Dogtown woods Rentals
From $672 per night (USD)VRBO
Stroll to SeaView\/Beach; Great Yard
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
The Ledge House is an idyllic retreat nestled in the heart of Gloucester's charming Bay View village. The historic farmh ...
From $672 per night (USD)VRBO
From $1664 per night (USD)Expedia
Maids Quarters; private beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This simple and quiet home is behind a Victorian mansion and was used as the Maid's quarters to house staff. It's now a ...
From $1664 per night (USD)Expedia
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The Quarry
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take it easy at this unique and tranquil magical getaway. What this place offers Lake view Public or shared beach access ...
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From $580 per night (USD)Expedia
Location Location Location walk to all the favorite Rockport attractions
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This 2 bedroom 1 full bath is super convenient. The property is walking distance to all the favorite Rockport attractio ...
From $580 per night (USD)Expedia
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The Solar Powered Dogtown Cabin at Applecart Farm
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walkin ...
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From $401 per night (USD)Expedia
Charming Coastal Cottage, Steps to Ocean & Rockport Village!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into the charming 1BR 1Bath cottage in a tranquil area just a few steps away from Shalin Liu Performance Center, ar ...
From $401 per night (USD)Expedia
From $505 per night (USD)VRBO
Amazing Waterfront\/Access 4BDRM in Riggs Point
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Come and relax at our amazing home fully equipped with everything to make you feel right at home. With spacious rooms to ...
From $505 per night (USD)VRBO
From $251 per night (USD)Expedia
Annisquam Village Bunny Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 ...
From $251 per night (USD)Expedia
From $142 per night (USD)VRBO
Cozy Cottage Old Fashioned Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Walk to beaches from this adorable old fashioned New England Style beach cottage when you book a stay with us. We are ...
From $142 per night (USD)VRBO
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Beautiful Rockport, steps to Front Beach, restaurants, shopping
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful fully furnished condo, just steps to Front Beach with ocean views. Accommodations for up to 4 guests, with se ...
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A walk up to heaven!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Very cozy Victorian home Fully renovated with brand new furniture and fresh paint Very convenient and plus location 5 ...
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From $595 per night (USD)Expedia
Tuna Wharf Townhouse has been sold and is no longer available to rent.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel free to contact me and I can refer you to other STR's Thanks! Jonathan Steps from the junction of Bearskin Ne ...
From $595 per night (USD)Expedia
From $213 per night (USD)VRBO
Quaint Home, Near Good Harbor Beach and Town, Great for Families
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
NOTE: We are currently only booking stays through May 2025. Check back later in the year for daily and weekly summer sta ...
From $213 per night (USD)VRBO
From $343 per night (USD)Expedia
Seaside Elegance with a Private Balcony – Wake Up to Harbor Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience coastal charm in The Captain's Quarters, a beautifully designed retreat at The Sail Loft. This inviting space ...
From $343 per night (USD)Expedia
From $215 per night (USD)VRBO
Cozy oceanfront home with unique architecture
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Rustic Rockport Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $215 per night (USD)VRBO
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Turning Tide Cottage on the Rivier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Nice deck with water views, small swimming beach,Bar-B-Que, large back lawn, on Annasquam river, close to downtown, easy ...
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From $626 per night (USD)VRBO
Cape Ann, Annisquam panoramic ocean views from every room.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
This charming shingled house, built in 1917 and respectfully renovated in recent years, sits atop a rocky hill overlooki ...
From $626 per night (USD)VRBO
From $521 per night (USD)Expedia
Clean Waterfront Classic Cottage with Private Beach
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Location x3! This classic, cozy, waterfront cottage that sits on a private beach overlooking the Annisquam River in Glou ...
From $521 per night (USD)Expedia
From $663 per night (USD)VRBO
Luxury Home in the Heart of Rockport
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Gorgeous house in Rockport, steps to beach, town, train, Shalin Liu performance center! This home is located on a quiet ...
From $663 per night (USD)VRBO
From $187 per night (USD)Expedia
WATERFRONT 1BDRM SPACIOUS STUDIO APARTMENT
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Come to the Cape named after a Queen NOT an Ugly Fish!! 🤣FABULOUS, quiet, dead end location! Incredible views of the An ...
From $187 per night (USD)Expedia
From $292 per night (USD)VRBO
A tranquil ocean retreat steps from the water's edge
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
On the Cove is a spacious three-room apartment is located directly on Lanes Cove in Lanesville (Gloucester) with spectac ...
From $292 per night (USD)VRBO
From $433 per night (USD)Expedia
Rockport Home with Beautiful Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 11
Enjoy stunningly beautiful ocean views from all 3 decks at this quirky 1820 colonial house with easy access to local ame ...
From $433 per night (USD)Expedia
From $286 per night (USD)VRBO
Dog-friendly apartment in a prime location - walk to town beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Olde New House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $286 per night (USD)VRBO
From $493 per night (USD)Expedia
'We can't wait to return to Four Winds'
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
PARKING SPOT 10 SECOND WALK AWAY, Four Winds is a two bedroom condo located directly on Tuna Wharf. If you love the sou ...
From $493 per night (USD)Expedia
From $320 per night (USD)VRBO
Quaint getaway with full kitchen and lush yard - close to the beach and downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Vintage Rockport Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $320 per night (USD)VRBO
From $445 per night (USD)Expedia
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to our idyllic retreat, the ultimate vacation spot for you, your family, and friends. Nestled between the picture ...
From $445 per night (USD)Expedia
From $594 per night (USD)VRBO
Downtown Home near the Beach & Downtown w\/Gas Grill, Washer\/Dryer & Deck
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
High Street Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $594 per night (USD)VRBO
From $726 per night (USD)Expedia
Gorgeous New Home w\/ Ocean Views- 2 Private Beaches Steps Away
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
THE HOME: This house was built in 2018 with every modern amenity and comfort for vacation life. Vaulted ceilings in the ...
From $726 per night (USD)Expedia
From $346 per night (USD)VRBO
Relax by the Sea – 3BR Rockport Retreat w\/ A\/C & Pets Welcome
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Just an hour from Boston, this classic New England cottage puts you right in the heart of Rockport—and yes, it’s real (e ...
From $346 per night (USD)VRBO
From $262 per night (USD)Expedia
NEW Rockport Studio · Walk to Bearskin Neck · Reserved Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
→ Perfect Rockport getaway only 5 minute walk to Old Garden Beach → Walk 5-10 minutes to Downtown Rockport where you'll ...
From $262 per night (USD)Expedia
From $262 per night (USD)VRBO
Harborside Oasis ★ Harbor View ★ Heart of Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
KEY FEATURES: 🌊 Sleeps 2 adults; 1 bedroom 🌊 Newly Renovated Modern Bathroom with standing shower 🌊 Modern and well-e ...
From $262 per night (USD)VRBO
From $425 per night (USD)Expedia
NEW 2BR Home Minutes to Downtown Rockport+Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This charming cottage is newly renovated with plenty of original character and fun details. Tucked away on a quiet lane ...
From $425 per night (USD)Expedia
From $235 per night (USD)VRBO
Chic Downtown Loft ☆ Private Parking ☆ Ocean View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy the coastal and seaside views from the renovated and bright "jewel" located in the charming seaside New England to ...
From $235 per night (USD)VRBO
From $287 per night (USD)Expedia
The Crow’s Nest – Loft with Stunning Ocean Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Perched above the heart of Bearskin Neck, The Crow’s Nest is a bright and airy studio apartment offering a cozy yet styl ...
From $287 per night (USD)Expedia
From $377 per night (USD)VRBO
Newly Renovated 2BR Rockport Home w\/ parking Steps to Back Beach+Bearskin Neck!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This charming seaside cottage is newly renovated with lots of modern conveniences and plenty of original character. You' ...
From $377 per night (USD)VRBO
From $410 per night (USD)Expedia
Beachmont: 3 bedroom house near beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Just 1/3 of a mile from Good Harbor Beach in East Gloucester! Enjoy a relaxing beach getaway in Historic Gloucester, MA. ...
From $410 per night (USD)Expedia
From $238 per night (USD)VRBO
Private Deck and Apartment in the treetops. The Admiral's Loft!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Close to downtown but set back on a quiet dead end street, The Admiral's Loft sits high in the treetops with keyhole vie ...
From $238 per night (USD)VRBO
From $367 per night (USD)Expedia
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Your cozy getaway awaits in Rockport at this brilliant house. With 2 bedrooms, a bathroom, and essential amenities like ...
From $367 per night (USD)Expedia
From $1064 per night (USD)VRBO
One of a kind ocean front property - private section of Wingaersheek Beach.
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 4
This property offers stunning views from every vantage point of Coffin's Beach, Crane Beach, the New Hampshire and Main ...
From $1064 per night (USD)VRBO
From $784 per night (USD)Expedia
Elegant Bayview Victorian Home; walk to beach
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Discover the historic charm of Bayview, a stunning private estate once home to Civil War General Benjamin F. Butler. Spa ...
From $784 per night (USD)Expedia
From $465 per night (USD)VRBO
NEW Home w\/firepit l Walk to Bearskin Neck+Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Set amidst a quiet oasis off the beaten path this exquisite shingled cape residence epitomizes refined elegance while ef ...
From $465 per night (USD)VRBO
From $474 per night (USD)VRBO
Oceanfront penthouse 2 bed 2 bath situated on beach and downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Renovated top floor apartment in the heart of the downtown Rockport historic district on the water. Deck with ocean view ...
From $474 per night (USD)VRBO
From $383 per night (USD)VRBO
NEW \"Tranquil Seas\" Rockport SUMMER Rental - Convenience, Comfort and Charm
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This meticulous, cozy, air conditioned home requires nothing but your suitcase and the desire to relax and have fun. Par ...
From $383 per night (USD)VRBO
From $607 per night (USD)Expedia
Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Riverdock Cottage was completely renovated in 2017 and has received some new updates for the 2022 rental season, includi ...
From $607 per night (USD)Expedia
From $534 per night (USD)VRBO
Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Greet each day with inspiring views of the Annisquam River from this charming vacation home and enjoy the most spectacul ...
From $534 per night (USD)VRBO
From $996 per night (USD)VRBO
Beach Front Luxe: Italian vibes & coastal glam in Rockport! Steps to Downtown!!!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
Enjoy a little bit of Italy in Coastal New England! Expansive Atlantic views, and steps to Front Beach, design enthusias ...
From $996 per night (USD)VRBO
From $826 per night (USD)VRBO
Granite Pier: Blends craftsmanship with modern amenities. Water views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Granite Pier, with its unparalleled ocean views, is a traditional Cape Ann home with an unusual history. Built in the mi ...
From $826 per night (USD)VRBO
From $208 per night (USD)VRBO
Cozy, Waterview Old Quarryman boarding house
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Adorable 1 bedroom (with memory foam folding cot for xtra guests) Sleep Sofa. Has foma topper, High ceilings, laundry, ...
From $208 per night (USD)VRBO
From $353 per night (USD)VRBO
\"Absolutely lovely. The cottage, the beach, the town, the owners.\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
A Breezy Cottage is a very short walk to the charming beaches of Rockport, MA. It comfortably sleeps up to 7 people inc ...
From $353 per night (USD)VRBO
From $894 per night (USD)VRBO
Family home – 40 Atlantic Ave., Rockport, MA. Minutes walk to town and beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Leave your car in the driveway and walk to beach and town: 4-minutes to secluded Old Garden Beach, the Atlantic Pat ...
From $894 per night (USD)VRBO
From $391 per night (USD)VRBO
The Waterline – A Private Harborfront Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in the historic Sail Loft building on Bearskin Neck, The Waterline offers a charming ground-floor retreat with s ...
From $391 per night (USD)VRBO
From $562 per night (USD)Expedia
Sunset Cove: Waterfront home in Goose Cove section of Gloucester.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river an ...
From $562 per night (USD)Expedia
From $603 per night (USD)VRBO
Ocean views just steps to Back Beach, Front Beach, and downtown Rockport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come enjoy the ocean in Rockport. Fully furnished 3 bedroom 2 bath charming antique home with updated kitchen and baths. ...
From $603 per night (USD)VRBO
From $584 per night (USD)Expedia
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 7
Get away from it all and unwind at this comfortable riverfront vacation retreat. Located in a quiet neighborhood, Thurst ...
From $584 per night (USD)Expedia
From $594 per night (USD)VRBO
Helena House: European flair, close to Plum Cove Beach.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Situated on a knoll in Gloucester's Bay View neighborhood, Helena House offers peekaboo views of Ipswich Bay from the se ...
From $594 per night (USD)VRBO
From $447 per night (USD)Expedia
Granite Cottage: Charming cottage in Rockport with private deck and views.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or, walk down the quiet lane to Granite Pier ...
From $447 per night (USD)Expedia
From $289 per night (USD)VRBO
You will love our location and will return for our hospitality!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
After the success of A Breezy Cottage, we set our sails on The Life of Reilly! The property was purchased in September, ...
From $289 per night (USD)VRBO
From $402 per night (USD)Expedia
Jewel Box: A gem of a rental home close to Good Harbor Beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Situated at the end of a quiet street and down the road from Good Harbor Beach, Jewel Box is a gem of a rental home. Thi ...
From $402 per night (USD)Expedia
Click For PricingVRBO
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You'll find river life at its best when you stay at this newly-built vacation rental home that sits along the banks of s ...
Click For PricingVRBO
From $677 per night (USD)Expedia
Squam Light: A newly renovated cottage, nestled in the village of Annisquam.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the ...
From $677 per night (USD)Expedia
From $227 per night (USD)VRBO
VIEWS! Annisquam Bridge House at Lobster Cove. June dates discounted.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Annisquam Bridge House-a renovated second floor unit high above Lobster Cove, Perfect getaway for a couple. It can acco ...
From $227 per night (USD)VRBO
From $386 per night (USD)Expedia
Sandy Bay: An oceanfront gem vacation rental with ocean views in Rockport.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to an oceanfront gem with exquisite views of Rockport's Sandy Bay and the Atlantic Ocean. Located just a short di ...
From $386 per night (USD)Expedia
From $969 per night (USD)VRBO
Landmark Lookout: Lovely views of Sandy Bay and the Atlantic Ocean.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy beautiful views of Sandy Bay and the Atlantic from this classic New England vacation rental home on Rockport's Pig ...
From $969 per night (USD)VRBO
From $1067 per night (USD)Expedia
Beach & King - Stunning Ocean Views!
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 14
Located across from Rockport's Front Beach, Beach & King is a beautiful Cape Ann Beach House rental on the North Shore i ...
From $1067 per night (USD)Expedia
From $303 per night (USD)VRBO
HEART OF HISTORICAL ROCKPORT with Reserved Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to the perfect romantic harborside retreat in Rockport, you will be mesmerized by the view. This 1,000 sq ft s ...
From $303 per night (USD)VRBO
From $499 per night (USD)VRBO
Private Pet Friendly hideaway near the beach and town center.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cottage on the Pond is tucked away from the summer crowds at the end of a picturesque lane with ocean views from the fro ...
From $499 per night (USD)VRBO
From $221 per night (USD)VRBO
Come home to Rockport!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Spend a weekend or a week enjoying the beauty and culture of Rockport. Enjoy panoramic views of Sandy Bay.and Straights ...
From $221 per night (USD)VRBO
From $884 per night (USD)Expedia
Sunrise on the Cove: Unobstructed 180 degree views of Pigeon Cove.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
From its waterfront perch, this vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor and has spectac ...
From $884 per night (USD)Expedia
From $437 per night (USD)VRBO
Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Just 4/10 of a mile from Gloucester's sandy Good Harbor Beach, Joseph's Way is delightful two bedroom property is nestle ...
From $437 per night (USD)VRBO
From $624 per night (USD)Expedia
Sea Glass on South: Modern rustic chic, just steps from downtown Rockport
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on the edge of the village of Rockport, Sea Glass on South is a brand new and modern retreat, inspired by the Ne ...
From $624 per night (USD)Expedia
From $342 per night (USD)VRBO
Historic charm meets contemporary comfort at Pigeon Hill.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Steeped in history, this traditional early victorian home has been newly remodeled and renovated blending original detai ...
From $342 per night (USD)VRBO
From $495 per night (USD)VRBO
Charming year round cottage - Pet Friendly with Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Please contact us for more details. We would love to discuss your vacation plans at our Home Away from Home. We are Pe ...
From $495 per night (USD)VRBO
From $405 per night (USD)VRBO
Seaside Village of Lanesville - North Gloucester, MA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This quaint, cozy, quiet two bedroom fully furnished apartment in the Village of Lanesville has views of the Ipswich Bay ...
From $405 per night (USD)VRBO
From $208 per night (USD)VRBO
Quaint Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Relax and breathe the salt air in this charming waterfront cottage. It is on well-known Bearskin Neck with a large deck ...
From $208 per night (USD)VRBO
From $443 per night (USD)VRBO
Waterfront House on Rockport’s \nOld Harbour Enjoy Spectacular Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This historical, 19th-century comfortable waterfront house is located in the heart of Rockport directly on Rockport's O ...
From $443 per night (USD)VRBO
From $275 per night (USD)VRBO
Picturesque Rockport Queen Anne Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Great location in beautiful Rockport. The house is a ten minute walk into town - Bearskin Neck shopping, art galleries, ...
From $275 per night (USD)VRBO
From $130 per night (USD)VRBO
Gloucester Studio - Om Suite Om~ near Good Harbor Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Om Suite Om is a comfortable, cozy and convenient studio efficiency space, with a separate key and entry, in the lower l ...
From $130 per night (USD)VRBO
From $656 per night (USD)Expedia
Beautiful vacation home. Reduced mos rates Oct-May. Plz contact for details.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to our charming 3-bedroom vacation home in the heart of Rockport, just a short walk from the Shalin Liu Performan ...
From $656 per night (USD)Expedia
From $586 per night (USD)VRBO
Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
This finely maintained summer cottage built in the 1820s overlooks Hodgkins Cove in Gloucester Massachusetts. Unique an ...
From $586 per night (USD)VRBO
From $653 per night (USD)VRBO
Rockport direct Waterfront 3 bedroom, 3 bathroom home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Breakwater House is a spacious contemporary home offering direct waterfront location in quiet, residential Pigeon Cove n ...
From $653 per night (USD)VRBO
From $184 per night (USD)VRBO
Seaside vacation studio steps from beaches and harbor area in historic Rockport
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 2
RESERVATIONS NOW BEING ACCEPTED FOR SUMMER 2023 starting May through October! Ground floor efficiency studio private r ...
From $184 per night (USD)VRBO
From $391 per night (USD)VRBO
Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy your vacation sojourn in this newly-renovated home, a short walk to one of New England's most beautiful beaches. ...
From $391 per night (USD)VRBO
From $473 per night (USD)VRBO
Bayview Guest Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
This property is a 650 sq. foot cozy cottage on Ipswich Bay with unbeatable views facing west, making for beautiful suns ...
From $473 per night (USD)VRBO
From $943 per night (USD)Expedia
Beautiful Oceanfront Home in Estate Setting, Gloucester
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
A spacious, beautiful contemporary home on a private oceanfront estate near Gloucester's coveted Annisquam district, wit ...
From $943 per night (USD)Expedia
From $469 per night (USD)VRBO
WaterViews Overlooking Gloucester Inner Harbor \/Sunroom\/ Deck \/Walk to Town\/ AC
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
VACATION or WORK or do a bit of both if it means you'll have longer to play here on Cape Ann! The preferred spot for all ...
From $469 per night (USD)VRBO
From $525 per night (USD)VRBO
Summer Cottage on Ipswich Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This quiet summer cottage was built in the 1890's, it's original charm has been retained, while updates have made it a c ...
From $525 per night (USD)VRBO
From $429 per night (USD)VRBO
Sunset Views, Waterfront Property, Dock - Sleeps 12
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Stunning sunsets, a parade of boats going by, a charming marina, and a beach brimming with natural beauty — these are th ...
From $429 per night (USD)VRBO
From $239 per night (USD)VRBO
Holbrook House: Charming Rockport Village House, Walk To Everything!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A cozy, lovingly restored 1950's house. Walking distance to all that Rockport village and Bear Skin Neck has to offer. ...
From $239 per night (USD)VRBO
From $652 per night (USD)VRBO
Brilliant Ocean Views. Two Cottages - One price.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
'Back Beach Cottages' is a unique property with a two cottage set up. Both houses have wonderful views of the ocean and ...
From $652 per night (USD)VRBO
From $550 per night (USD)VRBO
Experience seaside charm near Good Harbor Beach!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Come and enjoy this new home with roof top deck overlooking Good Harbor Beach. We are a 5 minute walk to the beach! We ...
From $550 per night (USD)VRBO
From $624 per night (USD)VRBO
Evensong: Oceanview Retreat with Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Unobstructed Water Views of The Annisquam in this newly-renovated "walls of glass" home boasting panoramic views of The ...
From $624 per night (USD)VRBO
From $370 per night (USD)VRBO
Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Our adorable, 3 bedroom home is in a prime location for your vacation, with plenty of windows for ocean breezes. If yo ...
From $370 per night (USD)VRBO
From $407 per night (USD)VRBO
Experience Rockport charm, walk to the beach ,restaurants & Shalin Liu Center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to our charming 3-bedroom vacation home in the heart of Rockport! Nestled just a short walk from the Shalin Liu ...
From $407 per night (USD)VRBO
From $223 per night (USD)VRBO
Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Immerse yourself in the heart of America's most famous seaside artists' colony. Located on Bearskin Neck and nestled in ...
From $223 per night (USD)VRBO
From $659 per night (USD)VRBO
Waterfront Home with Spectacular Viewsof the Annisquam River
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Watch the beautiful sunsets over the Annisquam River from the deck or just enjoy the scenic views all day long of Mercha ...
From $659 per night (USD)VRBO
From $372 per night (USD)VRBO
Quaint Simplicity on Quiet Lane, Spacious and Relaxing, Walk to Shops, Beaches
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This peaceful location on a quiet lane just outside of Rockport's downtown offers an easy place from which to enjoy the ...
From $372 per night (USD)VRBO
From $419 per night (USD)VRBO
Perfect Rockport Downtown Vacation Destination
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our fully renovated 3 bedroom cottage style unit offers all of the amenities needed for a perfect Rockport vacation. Ent ...
From $419 per night (USD)VRBO
From $354 per night (USD)VRBO
Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to a historical harborside treasure at our breathtaking 3rd-floor walk-up. As you step into the unit, prepare to ...
From $354 per night (USD)VRBO
From $787 per night (USD)VRBO
The Spinnaker: A hidden gem in Rockport village with roof deck and a garden.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Rockport village, The Spinnaker is the perfect rental home to feel worlds away from it all with a delightful ...
From $787 per night (USD)VRBO
From $319 per night (USD)Expedia
Single Level Home - Steps to Downtown Gloucester & A\/C throughout
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This darling property is private and steps to everything in Gloucester. We own both upstairs and downstairs units. The ...
From $319 per night (USD)Expedia