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Middlesex Area Rentals

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Results: 340 Rentals

  • Marina Guest House
    From $230 per night (USD)

    VRBO

    Marina Guest House

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This beautifully decorated, clean and comfortable space is 600 square feet, has one bedroom with a queen size bed, a ful ...

    From $230 per night (USD)

    VRBO

    Details
  • Historic Mansion 1841
    From $171 per night (USD)

    VRBO

    Historic Mansion 1841

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    The Mansion is a 3,200 square foot structure. You are renting 1 bedroom with a full en-suite bathroom on the first floor ...

    From $171 per night (USD)

    VRBO

    Details
  • Direct Lakefront, 2 docks, private, easy access from I 91.
    From $416 per night (USD)

    VRBO

    Direct Lakefront, 2 docks, private, easy access from I 91.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Rental of this property is subject to The State of Connecticut Travel Restrictions.This property is cleaned and disinfec ...

    From $416 per night (USD)

    VRBO

    Details
  • Driftwood Cottage @  Saybrook Point Marina, 2 King Beds
    From $568 per night (USD)

    Expedia

    Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Nestled between the Long Island Sound and the Connecticut River, Cove Street Cottage is your luxury getaway. You won’t h ...

    From $568 per night (USD)

    Expedia

    Details
  • Newly Remodeled 2 Bedroom Cottage On The Beach.  The Kaitlyn Cottage
    From $430 per night (USD)

    VRBO

    Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    If you are looking for a beach front property then look no further! This beautiful freshly remodeled 2 bedroom cottage s ...

    From $430 per night (USD)

    VRBO

    Details
  • The Perfect Family Beachfront Cottage  The Viola Cottage
    From $426 per night (USD)

    Expedia

    The Perfect Family Beachfront Cottage The Viola Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    <p>A short distance from sailing, windsurfing, and more, this beach cottage lets you experience it all. Jump into your c ...

    From $426 per night (USD)

    Expedia

    Details
  • 4BR Beach Cottage sits on private beach.  Sleeps 12 with comfort, Outdoor grill
    From $855 per night (USD)

    VRBO

    4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    OCEAN FRONT HOME WITH SPECTACULAR views of Duck Island and the Long Island Sound. The front of the house faces the Menu ...

    From $855 per night (USD)

    VRBO

    Details
  • Contemporary Loft Apartment
    From $172 per night (USD)

    VRBO

    Contemporary Loft Apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Spacious loft style apartment located on second floor with views of Long Island Sound. Single bedroom with Queen size ...

    From $172 per night (USD)

    VRBO

    Details
  • Romantic Lakefront Cottage #5
    From $265 per night (USD)

    VRBO

    Romantic Lakefront Cottage #5

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    This lovely renovated 1950's Lakefront Cottage is a perfect romantic get away. It boasts an open floor plan with kitche ...

    From $265 per night (USD)

    VRBO

    Details
  • Lovely Cottage by Lake Hayward
    From $236 per night (USD)

    VRBO

    Lovely Cottage by Lake Hayward

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Stay in this lovely, recently renovated cottage that is just a quick walk (or drive) to 3 lakeside beaches and just 30 m ...

    From $236 per night (USD)

    VRBO

    Details
  • Large, Comfortable Beach House with Shared Private Beach and Stunning Views
    From $833 per night (USD)

    VRBO

    Large, Comfortable Beach House with Shared Private Beach and Stunning Views

    Bedrooms:
    3
    Bathrooms:
    7
    Sleeps:
    10

    We have some prime weeks remaining for summer 2024. This lovely family vacation home has 5 bedrooms, 2.5 bathrooms (one ...

    From $833 per night (USD)

    VRBO

    Details
  • Seasonal cottage rental,waterview
    From $393 per night (USD)

    VRBO

    Seasonal cottage rental,waterview

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Guests are sure to enjoy a memorable vacation in this fully furnished, 3 bedroom/1 bath cottage. The space is comforta ...

    From $393 per night (USD)

    VRBO

    Details
  • Lake Front Home on the water
    From $480 per night (USD)

    VRBO

    Lake Front Home on the water

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    5 bedrooms, 3 & 1/2 bathrooms, sleeps up to 10 Beautiful renovated home on Lake Pocotopaug. This private 553 acre lake i ...

    From $480 per night (USD)

    VRBO

    Details
  • SeaStar Beach House \nCLOSE WALK TO OCEAN
    From $404 per night (USD)

    Expedia

    SeaStar Beach House \nCLOSE WALK TO OCEAN

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    *****SEASTAR****** Enjoy the beauty and Seascape of Knollwood Beach located in beautiful and scenic Old Saybrook Conne ...

    From $404 per night (USD)

    Expedia

    Details
  • Fun Lake Front Cottage!
    From $261 per night (USD)

    VRBO

    Fun Lake Front Cottage!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This cottage was lovingly remodeled with lake décor and fun in mind. Come enjoy this two bedroom with open living room ...

    From $261 per night (USD)

    VRBO

    Details
  • Cornfield Point Cottage
    From $1076 per night (USD)

    VRBO

    Cornfield Point Cottage

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    9

    Our NEWLY RENOVATED cozy cottage is right on the beach. 🏖 You can’t get any closer than a home on the beach. Great fish ...

    From $1076 per night (USD)

    VRBO

    Details
  • ๐ŸŒ…A Lakefront Sunrise retreat for Couples or Families๐ŸŒ…
    From $621 per night (USD)

    VRBO

    🌅A Lakefront Sunrise retreat for Couples or Families🌅

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Welcome to Lake Pocotopaug! Enjoy four seasons of fun, relaxation and adventure! This lakefront destination offers it a ...

    From $621 per night (USD)

    VRBO

    Details
  • Family Friendly, Beach Themed Cottage - Chalker Beach
    From $259 per night (USD)

    VRBO

    Family Friendly, Beach Themed Cottage - Chalker Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This is a beautiful, Cape Cod style cottage that is only an 8 minute walk from the beach. Located in the private Chalker ...

    From $259 per night (USD)

    VRBO

    Details
  • Charming Quiet Updated 1921 Cottage West Beach Connecticut
    From $256 per night (USD)

    VRBO

    Charming Quiet Updated 1921 Cottage West Beach Connecticut

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Second cottage see VRBO #342736 is also available at the front of the property, for vacations with extended family and f ...

    From $256 per night (USD)

    VRBO

    Details
  • Charming Cottage with L.I. Sound and Marsh Views
    From $330 per night (USD)

    VRBO

    Charming Cottage with L.I. Sound and Marsh Views

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Completely renovated beach home directly across the street from one house on a private beach. Enjoy water views of Long ...

    From $330 per night (USD)

    VRBO

    Details
  • You and your Family deserve a break. Relax and enjoy lake front living
    From $377 per night (USD)

    VRBO

    You and your Family deserve a break. Relax and enjoy lake front living

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    2 story lake front cottage. Sleeps 8 in 2-Bedrooms 10 steps off the rear deck lies the Modus Reservoir, a 450 acre fresh ...

    From $377 per night (USD)

    VRBO

    Details
  • 5 Bedroom Cottage Steps From The Beach @ Great Hammock Beach - JULY RENTAL ONLY
    From $402 per night (USD)

    VRBO

    5 Bedroom Cottage Steps From The Beach @ Great Hammock Beach - JULY RENTAL ONLY

    Bedrooms:
    1
    Bathrooms:
    5
    Sleeps:
    12

    We are booked for the 2022 season! Check back with us next year! We will not reply to any inquiries for 2022. Thank yo ...

    From $402 per night (USD)

    VRBO

    Details
  • Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach
    From $270 per night (USD)

    VRBO

    Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Chalker Beach has been part of our family since 1966; come and enjoy our cozy renovated vintage cottage. Two bedrooms co ...

    From $270 per night (USD)

    VRBO

    Details
  • OCEAN\/BEACH FRONT, HUGE YARD, SUNSET VIEW
    From $783 per night (USD)

    Expedia

    OCEAN\/BEACH FRONT, HUGE YARD, SUNSET VIEW

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Ocean front, sunset facing, property is the only one in the area that has a huge yard and beach. 4-bedrooms, beautiful ...

    From $783 per night (USD)

    Expedia

    Details
  • Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino
    From $1133 per night (USD)

    VRBO

    Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    What you will LOVE - PRIVATE RESORT STYLE PATIO - stunning pool, hot tub, cabana bar and grill, 65" TV and more! Tons o ...

    From $1133 per night (USD)

    VRBO

    Details
  • Luxury Waterfront Home-August 18-23 still available.
    From $810 per night (USD)

    VRBO

    Luxury Waterfront Home-August 18-23 still available.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Perched along a luxurious peninsula jutting into the Long Island Sound, the Obstreperous Octopus sinks its tentacles int ...

    From $810 per night (USD)

    VRBO

    Details
  • Family compound, vintage 1872 cottage water views
    From $304 per night (USD)

    VRBO

    Family compound, vintage 1872 cottage water views

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    A second cottage (see VRBO #394631) is also available at the back of the property if you'd like to rent both. A large l ...

    From $304 per night (USD)

    VRBO

    Details
  • Spacious And Luxurious Beach Home Steps From The Water
    From $547 per night (USD)

    Expedia

    Spacious And Luxurious Beach Home Steps From The Water

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    This house is perfect for families or groups that want to enjoy beautiful Old Saybrook in a spacious, newly remodeled, t ...

    From $547 per night (USD)

    Expedia

    Details
  • LAKE HOUSE! Walking distance to Lake Pocotopaug!
    From $321 per night (USD)

    VRBO

    LAKE HOUSE! Walking distance to Lake Pocotopaug!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to The Mohawk Cottage! Perfectly located walking distance to Lake Pocotopaug in East Hampton, Connecticut. Our ...

    From $321 per night (USD)

    VRBO

    Details
  • Romantic Cottage by the Sea, steps to private beach, sleeps 2!
    From $256 per night (USD)

    VRBO

    Romantic Cottage by the Sea, steps to private beach, sleeps 2!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This adorable little studio cottage is located in a private association with beach just 200 steps away! The property ha ...

    From $256 per night (USD)

    VRBO

    Details
  • Paradise in Clinton! AIR-CONDITIONED
    From $1782 per night (USD)

    VRBO

    Paradise in Clinton! AIR-CONDITIONED

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    This ocean front luxurious 4 bedroom 3 bath is a dream home in a high-end community located in Clinton, Connecticut. T ...

    From $1782 per night (USD)

    VRBO

    Details
  • Charming Beach House - Steps to private beach! Sleeps 4
    From $402 per night (USD)

    VRBO

    Charming Beach House - Steps to private beach! Sleeps 4

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This adorable house is located in a great private beach community, 6 houses away from beach (200 steps!) with a water vi ...

    From $402 per night (USD)

    VRBO

    Details
  • Family friendly beachfront escape
    From $1140 per night (USD)

    VRBO

    Family friendly beachfront escape

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Relax and spend time with family on this beautiful beachfront home! Originally built in 1890, this newly renovated bunga ...

    From $1140 per night (USD)

    VRBO

    Details
  • Saybrook Almost Beach-Front, Private Beach,  Boat Launch, Shallow Dock, Secluded
    From $419 per night (USD)

    VRBO

    Saybrook Almost Beach-Front, Private Beach, Boat Launch, Shallow Dock, Secluded

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    This water view, beach access home is located just one house away from the beach. The house features four bedrooms, one ...

    From $419 per night (USD)

    VRBO

    Details
  • Stunning cottage
    From $380 per night (USD)

    VRBO

    Stunning cottage

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    6

    Great Hammock beach is an exceptional summer community with fishing, swimming and kayaking. enjoy walking the beautiful ...

    From $380 per night (USD)

    VRBO

    Details
  • Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
    From $531 per night (USD)

    Expedia

    Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    13

    Amazing Waterview Getaway with All the Essentials Experience a fantastic coastal escape just steps away from breathtaki ...

    From $531 per night (USD)

    Expedia

    Details
  • Beautiful Cottage Cove!
    From $442 per night (USD)

    VRBO

    Beautiful Cottage Cove!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Come stay at this tastefully updated 4 bedroom-2.5 bath home. Large kitchen and spacious rooms. Each room has its own TV ...

    From $442 per night (USD)

    VRBO

    Details
  • Cozy, Beach Cottage on West Beach
    From $322 per night (USD)

    VRBO

    Cozy, Beach Cottage on West Beach

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Cozy cottage, with water views, steps from West Beach and Coral Sands Beach. A wonderful family community with many recr ...

    From $322 per night (USD)

    VRBO

    Details
  • 3+BR\/ 2 bath in Grove Beach Improvement Association Community... Central AC
    From $398 per night (USD)

    VRBO

    3+BR\/ 2 bath in Grove Beach Improvement Association Community... Central AC

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Looking for a quintessential family vacation on the Connecticut shore? Our family vacation home has Central Air, 3 bedr ...

    From $398 per night (USD)

    VRBO

    Details
  • Waterfront Retreat overlooking Long Island Sound w\/gorgeous sunrises & sunsets!
    From $546 per night (USD)

    VRBO

    Waterfront Retreat overlooking Long Island Sound w\/gorgeous sunrises & sunsets!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    *******************************************NOTE************************************************** I DO NOT LIST THIS PRO ...

    From $546 per night (USD)

    VRBO

    Details
  • Spectacular Lakefront home with expansive decks
    From $384 per night (USD)

    VRBO

    Spectacular Lakefront home with expansive decks

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    8

    Escape to charming Lake front home with water views from virtually every room. Indoor/outdoor living at it's best with ...

    From $384 per night (USD)

    VRBO

    Details
  • Luxurious Beach Home!
    From $784 per night (USD)

    VRBO

    Luxurious Beach Home!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Enjoy you vacation time at this Newly Remodeled Luxurious Beach Home,With two first floor full Baths and bedrooms With ...

    From $784 per night (USD)

    VRBO

    Details
  • Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
    From $224 per night (USD)

    VRBO

    Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Our Great Hammock Beach cottage is a seasonal rental with 4 bedrooms and 1 bath. Recently installed central air conditio ...

    From $224 per night (USD)

    VRBO

    Details
  • Charming Lakefront Home with Sunset Views
    From $476 per night (USD)

    VRBO

    Charming Lakefront Home with Sunset Views

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    Newly renovated home on beautiful Lake Pocotopaug. This private 650-acre lake is closed to the public! Located in a sm ...

    From $476 per night (USD)

    VRBO

    Details
  • Upscale Beach Home!!
    From $761 per night (USD)

    VRBO

    Upscale Beach Home!!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Thinking of having your wedding at Waters Edge? Stay at this beautiful beach home . . Relax at this Newly Remodeled Spac ...

    From $761 per night (USD)

    VRBO

    Details
  • Charming Beach House With Totally Private Backyard - 500 Ft. From Private Beach
    From $262 per night (USD)

    VRBO

    Charming Beach House With Totally Private Backyard - 500 Ft. From Private Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    (Disregard the GPS map - The beach house is 500 feet from Island View Beach) This cozy and very clean beach house offer ...

    From $262 per night (USD)

    VRBO

    Details
  • Private Access Studio_king bed_WiFi_all the amenities of a hotel_5โญ๏ธ experience
    Click For Pricing

    VRBO

    Private Access Studio_king bed_WiFi_all the amenities of a hotel_5⭐️ experience

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Everything you need for your overnight stay! Rest peacefully in the king size bed. Wake to a cup of coffee with your cho ...

    Click For Pricing

    VRBO

    Details
  • Modern Middletown Retreat, Minutes to Downtown!
    From $309 per night (USD)

    Expedia

    Modern Middletown Retreat, Minutes to Downtown!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    6

    Whether you’re visiting family, seeking outdoor adventure, or simply exploring a new area, this sleek 3-bedroom, 1-bathr ...

    From $309 per night (USD)

    Expedia

    Details
  • Large Charming Historic House close to Beaches
    From $474 per night (USD)

    VRBO

    Large Charming Historic House close to Beaches

    Bedrooms:
    2
    Bathrooms:
    6
    Sleeps:
    11

    This lovely family home has 6 bedrooms and 2 full baths and is close to downtown Clinton, Clinton Marina and many restau ...

    From $474 per night (USD)

    VRBO

    Details
  • Stroll to beach at charming, historical, rustic home w\/expansive yard & pool.
    From $695 per night (USD)

    VRBO

    Stroll to beach at charming, historical, rustic home w\/expansive yard & pool.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Charming, spacious, historical, artistic home walking distance to beach. Private yet centrally located; relaxing propert ...

    From $695 per night (USD)

    VRBO

    Details
  • Chic waterside Bungalow is stylish and secluded with harbor and beach views.
    From $411 per night (USD)

    VRBO

    Chic waterside Bungalow is stylish and secluded with harbor and beach views.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Just two doors from Old Harbor Marina and Clinton Town Beach, this cozy getaway is located on one of Connecticut's most ...

    From $411 per night (USD)

    VRBO

    Details
  • Bimbadeen Loft: Huge Open Plan 2-bedroom! Bring the boat, kids, and the dog!
    From $288 per night (USD)

    Expedia

    Bimbadeen Loft: Huge Open Plan 2-bedroom! Bring the boat, kids, and the dog!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Gorgeous NEW loft apartment on our country property! Enjoy views of the surrounding forest from the open-space living ar ...

    From $288 per night (USD)

    Expedia

    Details
  • Exquisite Beach Villa In Ground pool and Spacious Bermuda room! 2 living Rooms!
    Click For Pricing

    VRBO

    Exquisite Beach Villa In Ground pool and Spacious Bermuda room! 2 living Rooms!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Elegant 3200 Sq. Ft. Home on Private setting, with 2 Living Rooms, Bermuda room with Large in ground pool! Gourmet Kit ...

    Click For Pricing

    VRBO

    Details
  • Spacious Lake Hayward Cottage
    Click For Pricing

    Expedia

    Spacious Lake Hayward Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Forget your worries in this spacious and serene space. This 1,400+ Sq/Ft cottage is just a short 0.1 mile walk to Lake H ...

    Click For Pricing

    Expedia

    Details
  • Charming Old Saybrook Home: Half-Mi to Sand & Sea!
    Click For Pricing

    VRBO

    Charming Old Saybrook Home: Half-Mi to Sand & Sea!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Complement your next escape to the Connecticut coastline with a stay at this charming Old Saybrook vacation rental! Loca ...

    Click For Pricing

    VRBO

    Details
  • Charming private home on the Connecticut River that comfortably sleeps 11 people
    From $333 per night (USD)

    VRBO

    Charming private home on the Connecticut River that comfortably sleeps 11 people

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    Beautiful River Views and River Access! This unique 5 bed, 2 full bath contemporary sits on 1.39 acres of tranquil, priv ...

    From $333 per night (USD)

    VRBO

    Details
  • East Haddam Country Loft......
    From $267 per night (USD)

    VRBO

    East Haddam Country Loft......

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Bring the whole family and friends to this great place with lots of room for fun. Outdoor picnic table for 15, Grill, Ha ...

    From $267 per night (USD)

    VRBO

    Details
  • Upscale Bungalow with garden and Long Island Sound views. Walk to beach!
    From $400 per night (USD)

    VRBO

    Upscale Bungalow with garden and Long Island Sound views. Walk to beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy views of the Long Island Sound in these beautiful New England Bungalows. Walk to Clinton Beach. Queen Bed, Full Ki ...

    From $400 per night (USD)

    VRBO

    Details
  • COZY Maple Tree Cabin - Situated on 6 private acres - Get Away and RELAX ๐Ÿ˜Ž
    From $466 per night (USD)

    VRBO

    COZY Maple Tree Cabin - Situated on 6 private acres - Get Away and RELAX 😎

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    A quiet - peaceful place for families to enjoy. Also a great place for a couples retreat/romantic getaway. Get away fro ...

    From $466 per night (USD)

    VRBO

    Details
  • Old Saybrook family gem very close to local beaches!
    From $481 per night (USD)

    Expedia

    Old Saybrook family gem very close to local beaches!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    8

    Five bedroom family friendly home and the best of Old Saybrook. Our home is close to the beaches, dozens of fine restau ...

    From $481 per night (USD)

    Expedia

    Details
  • Waterfront home in the town of Old Saybrook, CT, walk to beach in a minute.
    From $1201 per night (USD)

    VRBO

    Waterfront home in the town of Old Saybrook, CT, walk to beach in a minute.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Welcome to our home. The beach is just a minute or 2 away from the home. Truly magically sunrise. If you are on the back ...

    From $1201 per night (USD)

    VRBO

    Details
  • 11 Mi to Powder Ridge Mountain: Connecticut Home
    From $652 per night (USD)

    Expedia

    11 Mi to Powder Ridge Mountain: Connecticut Home

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Seeking a serene and secluded vacation rental in Killingworth, CT? Search no further! Conveniently located near beaches, ...

    From $652 per night (USD)

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    Details
  • Coastal Cottage !3 bedroom, 2 bath home with deck and walk to the beach\n
    From $390 per night (USD)

    VRBO

    Coastal Cottage !3 bedroom, 2 bath home with deck and walk to the beach\n

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Enjoy oceanside walks, cool summer breezes, local beaches and amazing sunsets. Have fun looking for shells, catching cra ...

    From $390 per night (USD)

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    Details
  • New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
    From $848 per night (USD)

    Expedia

    New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Got college visits coming up? Local weddings?Halfway between Boston and NYC. Very near Yale and Wesleyan Universities. ...

    From $848 per night (USD)

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    Details
  • Private Apt in Middletown-Wesleyan
    From $277 per night (USD)

    VRBO

    Private Apt in Middletown-Wesleyan

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to our charming apartment located in the heart of Middletown, just a stone's throw away from Wesleyan University ...

    From $277 per night (USD)

    VRBO

    Details
  • Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
    From $762 per night (USD)

    Expedia

    Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Charming Coastal Retreat – Two-Unit Getaway Near the Beach! Experience the charm of Westbrook, CT, in this adorable coa ...

    From $762 per night (USD)

    Expedia

    Details
  • Equestrian Living: It's a lifestyle \Living on the Farm\ Not your ordinary Stay!
    From $623 per night (USD)

    VRBO

    Equestrian Living: It's a lifestyle \"Living on the Farm\" Not your ordinary Stay!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    "Living on the Farm" The Estate quarters are gorgeous, everything you would expect from Luxury Living like on Yellowston ...

    From $623 per night (USD)

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  • Life on the Farm
    From $174 per night (USD)

    VRBO

    Life on the Farm

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Imagine living on a horse farm! Enjoy the wildlife, and watch horses graze right from your steps. Relax, at this unique ...

    From $174 per night (USD)

    VRBO

    Details
  • Waterfront Lakehouse in Clinton, CT with Hot Tub!
    From $834 per night (USD)

    VRBO

    Waterfront Lakehouse in Clinton, CT with Hot Tub!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Embrace lakeside serenity at our inviting Lakehouse retreat. With modern comforts and tranquil surroundings, it comforta ...

    From $834 per night (USD)

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    Details
  • Luxe Lake House in Connecticut
    From $904 per night (USD)

    Expedia

    Luxe Lake House in Connecticut

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Take the peaceful lakeside escape you've been craving at this 5-bedroom, 3.5-bath vacation rental in Higganum, CT! 2 hou ...

    From $904 per night (USD)

    Expedia

    Details
  • Charming 2-bedroom farm cottage in quiet Killingworth neighborhood
    From $207 per night (USD)

    VRBO

    Charming 2-bedroom farm cottage in quiet Killingworth neighborhood

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Spring is here! Come get away and immerse yourself in the beauty of Killingworth. Experience a quiet getaway at this wel ...

    From $207 per night (USD)

    VRBO

    Details
  • Charming 3-bedroom cottage in Old Saybrook with AC, WiFi
    From $393 per night (USD)

    Expedia

    Charming 3-bedroom cottage in Old Saybrook with AC, WiFi

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Make memories at this Old Saybrook summer home, just a 2-minute walk to your private neighborhood beach! This charming c ...

    From $393 per night (USD)

    Expedia

    Details
  • Family Stays: Middletown, CT
    From $224 per night (USD)

    VRBO

    Family Stays: Middletown, CT

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Centrally Located Cozy Family Vacation Home: Just 1.2 miles from Wesleyan University, our space is perfect for families, ...

    From $224 per night (USD)

    VRBO

    Details
  • New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan
    From $384 per night (USD)

    Expedia

    New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Don't miss this fully renovated 2nd floor family friendly 3br apt in a historic home built in 1829. Formerly owned by ...

    From $384 per night (USD)

    Expedia

    Details
  • The Old Salt Cottage ยท Walk to Beach, Waters Edge
    From $547 per night (USD)

    VRBO

    The Old Salt Cottage · Walk to Beach, Waters Edge

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Grab your flip-flops and bathing suit and let your beach vacation begin! Located within walking distance to the private ...

    From $547 per night (USD)

    VRBO

    Details
  • Alongside ski area.  Charming house in Middlefield, 2 hrs from NY or Boston
    From $419 per night (USD)

    Expedia

    Alongside ski area. Charming house in Middlefield, 2 hrs from NY or Boston

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    This 3-bedroom house in Middlefield is perfect for your winter escape. With many nearby attractions, Lyman Orchards, Po ...

    From $419 per night (USD)

    Expedia

    Details
  • Coastal Connecticut Waters Edge Resort and Spa Long Island Sound Westbrook, CT
    From $345 per night (USD)

    VRBO

    Coastal Connecticut Waters Edge Resort and Spa Long Island Sound Westbrook, CT

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located in Westbrook, CT at Water's Edge Resort and Spa timeshare condo 3 restaurants, outdoor patio, beach, indoor/outd ...

    From $345 per night (USD)

    VRBO

    Details
  • Charming 4-bedroom house in Ivoryton\/Essex
    From $439 per night (USD)

    Expedia

    Charming 4-bedroom house in Ivoryton\/Essex

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Nestled in the village of Ivoryton, just outside the picturesque town of Essex and a stone's throw from the beautiful Bu ...

    From $439 per night (USD)

    Expedia

    Details
  • Shoreline Oasis
    From $261 per night (USD)

    VRBO

    Shoreline Oasis

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Keep it simple at this peaceful little oasis located in a quiet neighborhood, but close to all the fun stuff! We are a 5 ...

    From $261 per night (USD)

    VRBO

    Details
  • Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
    From $391 per night (USD)

    Expedia

    Charming 3-bedroom cottage in Old Saybrook with WiFi and AC

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Welcome to this seasonal, summer cottage located in the picturesque Great Hammock community of Old Saybrook, CT. This ch ...

    From $391 per night (USD)

    Expedia

    Details
  • Beautifully renovated, beach front home in charming Westbrook.
    From $717 per night (USD)

    VRBO

    Beautifully renovated, beach front home in charming Westbrook.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    **NEW THIS SUMMER ** Welcome to “The Beach House”! Our newly renovated home in Westbrook CT, located directly across t ...

    From $717 per night (USD)

    VRBO

    Details
  • Charming 1-bedroom apartment with AC, 3 minute walk to beach, and new hot tub
    From $275 per night (USD)

    Expedia

    Charming 1-bedroom apartment with AC, 3 minute walk to beach, and new hot tub

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to your perfect getaway! Recently renovated for comfort and style, this charming and cozy retreat offers everyth ...

    From $275 per night (USD)

    Expedia

    Details
  • Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
    From $431 per night (USD)

    VRBO

    Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Imagine the clinking of glasses, laughter and friendship during prohibition. This was Pierre Houpert's private distiller ...

    From $431 per night (USD)

    VRBO

    Details
  • Little Cottage of Gratitude Saybrook Manor walk to beach
    From $320 per night (USD)

    Expedia

    Little Cottage of Gratitude Saybrook Manor walk to beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This adorable cottage features a cozy coastal decor. Sleep in a queen or full bedroom or the queen sleeper sofa in the ...

    From $320 per night (USD)

    Expedia

    Details
  • Modern oceanfront home on West Beach
    From $538 per night (USD)

    VRBO

    Modern oceanfront home on West Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Experience New England charm while you enjoy the sunset and breathtaking views from our deck or loft. Directly across fr ...

    From $538 per night (USD)

    VRBO

    Details
  • Saltwater Gospel-Indian Town, Old Saybrook CT
    From $392 per night (USD)

    Expedia

    Saltwater Gospel-Indian Town, Old Saybrook CT

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to 58 Nehantic Trail, Old Saybrook CT. Located in the beach community of Indiantown within walking distance to ...

    From $392 per night (USD)

    Expedia

    Details
  • Beautiful Marsh Views in a Beach Community
    From $337 per night (USD)

    VRBO

    Beautiful Marsh Views in a Beach Community

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Sun-filled home within a bike ride to a private beach community with gorgeous marsh views and access to a private dock. ...

    From $337 per night (USD)

    VRBO

    Details
  • Escape to your lakeside paradise
    From $762 per night (USD)

    Expedia

    Escape to your lakeside paradise

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to our stunning 4-bedroom, 2.5-bathroom lake house that boasts luxurious amenities and breathtaking views. This ...

    From $762 per night (USD)

    Expedia

    Details
  • The Beach Nest-Lux Cottage Steps to the Beach
    From $369 per night (USD)

    VRBO

    The Beach Nest-Lux Cottage Steps to the Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Come enjoy the cutest cottage on Shore Rd. Newly renovated. Just steps to the beach and minutes away from town and all o ...

    From $369 per night (USD)

    VRBO

    Details
  • Tiffany's Oasis on the Shore
    From $645 per night (USD)

    VRBO

    Tiffany's Oasis on the Shore

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    9

    *Inquire for long term rentals* Nestled across from a private beach, this Pilots Point gem provides for a spacious and ...

    From $645 per night (USD)

    VRBO

    Details
  • Charming Chester Retreat- Near Village Center
    From $254 per night (USD)

    VRBO

    Charming Chester Retreat- Near Village Center

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This thoughtfully designed and smartly decorated 2 bed, 1 bath unit is the perfect blend of style and comfort. The space ...

    From $254 per night (USD)

    VRBO

    Details
  • Cozy Cottage On Star Lake
    From $246 per night (USD)

    Expedia

    Cozy Cottage On Star Lake

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Relax and enjoy this unique and tranquil getaway. Gorgeous lake house remolded in 2021. Enjoy the kitchen with stainless ...

    From $246 per night (USD)

    Expedia

    Details
  • Country getaway in 2 family home, huge yard & grounds, minutes from lakes & more
    From $356 per night (USD)

    VRBO

    Country getaway in 2 family home, huge yard & grounds, minutes from lakes & more

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Cozy rental unit in a historic 2-family home. With a private deck and outdoor shower & full use of the 4 acre property. ...

    From $356 per night (USD)

    VRBO

    Details
  • Newly Renovated Beach Cottage in Old Saybrook CT - AIR CONDITIONED!
    From $393 per night (USD)

    VRBO

    Newly Renovated Beach Cottage in Old Saybrook CT - AIR CONDITIONED!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Sparkling clean, fully air-conditioned, quiet and comfortable 2 bedroom, 1 1/2 bath cottage, summer weeks still availabl ...

    From $393 per night (USD)

    VRBO

    Details
  • 1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
    From $182 per night (USD)

    VRBO

    1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    In the delightful town of Clinton lies a snug one-bedroom cottage, ideal for your upcoming getaway. Surrounded by the na ...

    From $182 per night (USD)

    VRBO

    Details
  • Seaside Beach Haven with a private beach!
    From $1025 per night (USD)

    Expedia

    Seaside Beach Haven with a private beach!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    10

    Summary: This stunning beachfront home has 3 bedrooms & 3.5 bathrooms and sleeps 10 guests! It is the perfect sunny esca ...

    From $1025 per night (USD)

    Expedia

    Details
  • Beach House steps to private beaches in sought after location!
    From $406 per night (USD)

    VRBO

    Beach House steps to private beaches in sought after location!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    You will fall in love with this beautiful beach house in the sought-after Indian Town beach. Beautiful views of Harvey B ...

    From $406 per night (USD)

    VRBO

    Details
  • #24 *Serenity* A Lakefront Cottage Retreat
    From $349 per night (USD)

    Expedia

    #24 *Serenity* A Lakefront Cottage Retreat

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Closed the month of November for some exciting new upgrades! Stunning FALL FOLIAGE & WINTER VIEWS! This Lakefront Cott ...

    From $349 per night (USD)

    Expedia

    Details
  • Tiny Lakefront Cottage!
    From $199 per night (USD)

    VRBO

    Tiny Lakefront Cottage!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This lake front cottage is approx. 325sq. of adorable efficiency living space. It has an open floor plan with full siz ...

    From $199 per night (USD)

    VRBO

    Details
  • Cozy Cottage at The Cabins
    From $177 per night (USD)

    VRBO

    Cozy Cottage at The Cabins

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    A recently renovated one bedroom cottage in historic Westbrook, a quaint shoreline community on the banks of Long Island ...

    From $177 per night (USD)

    VRBO

    Details