Pinkwink Pond, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Pinkwink Pond, Massachusetts on RentalSaver.com!

Pinkwink Pond Rentals

From $635 per night (USD)
VRBO
4 Bedrooms, 2 Baths, Sleeps 8-10
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Location! Location! Location! The “Woodford Reserve” for fun and respite! This is classic cape cod home with four bedro ...
From $635 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Pet friendly and waterfront!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This beautiful home overlooking Emery Pond is spacious with 3 bedroom and 1 and half baths. With 1 queen, 2 twins and a ...
From $669 per night (USD)
Expedia
Click For Pricing
VRBO
Pet Friendly in Riverbay! Nicely furnished 3 bedroom, 2 full bath home in quiet Riverbay.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Perfect home for a family vacation! Nicely furnished 3 bedroom, 2 full bath home in quiet Riverbay. There is a queen be ...
Click For Pricing
VRBO
From $722 per night (USD)
Expedia
Updated Chatham Inn Home | Spacious Deck & Private Heated Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Stepping Stones -- Old Chatham Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $722 per night (USD)
Expedia
From $695 per night (USD)
VRBO
Spacious home in quiet neighborhood!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious three bedroom, two and half bath home in Riverbay offers plenty of living space on a 1/2 acre wooded corner lot ...
From $695 per night (USD)
VRBO
From $1268 per night (USD)
Expedia
Pet friendly! Beautiful decor and great outdoor entertaining space for the whole family.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy your Chatham vacation at this spacious, newly furnished, 4 bedroom, 3 bath home. Offering 1 king, 2 queens, a bunk ...
From $1268 per night (USD)
Expedia
From $372 per night (USD)
VRBO
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This adorable cottage is in an ideal location in West Chatham! Located on a quiet cul-de-sac with five other homes. A 5 ...
From $372 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Waterfront on Private Lake!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: 16644 - Lover's Lookout: Waterfront on Private Lake! The Space: Enjoy your best days of summer at our waterfro ...
From $406 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Updated Chatham cottage with privacy, nautical decor and lovely backyard.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy Chatham home set back from the road for privacy and nautical decor throughout. There is a gourmet kitchen with stai ...
From $451 per night (USD)
VRBO
$Great Chatham Location w\/ Hot Tub, Near Beach!$
From $854 per night (USD)
Expedia
Great Chatham Location w\/ Hot Tub, Near Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: 16650 - The Beach Buoys: Great Chatham Location w/ Hot Tub, Near Beach! The Space: Access to beaches, a quinte ...
From $854 per night (USD)
Expedia
From $742 per night (USD)
VRBO
Hot Tub, Fenced Yard & Dog Friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Summary: 16651 - Smooth Sailing: Hot Tub, Fenced Yard & Dog Friendly The Space: Keep it classy this summer and spend a ...
From $742 per night (USD)
VRBO
$Spacious w\/ Large Outdoor Area Fire Pit!$
From $451 per night (USD)
Expedia
Spacious w\/ Large Outdoor Area Fire Pit!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16637 - The Driftwood: Spacious w/ Large Outdoor Area Fire Pit! The Space: Our beautifully decorated, spacious ...
From $451 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Quintessential Chatham Cottage by the Pond
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
If a true Cape Cod cottage is what you are looking for, your search ends here. Steps from Schoolhouse Pond, you can for ...
From $367 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Beautifully Renovated Cape on Bike Trail, 1 mile to Downtown Chatham and Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Charming Cape house recently renovated less than a mile to Downtown Chatham for shopping and restaurants. Located on a q ...
From $270 per night (USD)
VRBO
From $570 per night (USD)
VRBO
Wifi, AC, 4 bedrooms, 3 bathrooms, additional sleep space and bonus living room in the lower level
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
3 Bedroom - 3 Bath - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $570 per night (USD)
VRBO
From $1122 per night (USD)
Expedia
Luxury Waterfront with Game Room!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: 16693 - Chatham Homecoming: Luxury Waterfront with Game Room! The Space: Perched above the shimmering waters o ...
From $1122 per night (USD)
Expedia
From $728 per night (USD)
VRBO
Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Book your Cape Cod escape where location, historic charm, and value unite! Our beautifully preserved and updated 1930s h ...
From $728 per night (USD)
VRBO
From $576 per night (USD)
VRBO
3BR - Large Fenced In Yard, Patio, Near Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Location: Located on a dead-end road near the head of Pleasant Bay, this 3 bedroom house offers a large fenced in yard w ...
From $576 per night (USD)
VRBO
From $1460 per night (USD)
VRBO
Luxury Family Fun - Heated Pool, Hot Tub, Game Room, Walk to Small Beach - 5BR
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home featur ...
From $1460 per night (USD)
VRBO
From $1104 per night (USD)
VRBO
Perfect House to Enjoy Family & Friends!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Main house has 3 bedrooms 2 baths. Open floor plan is great for a big group. Apartment has a full kitchen, living area a ...
From $1104 per night (USD)
VRBO
From $746 per night (USD)
VRBO
New July dates! Sun drenched Cape haven- spectacular deck, garden & patio!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Relax and revive in this airy, modern and beautifully appointed 2600 square ft. Cape Cod home in a lovely secluded neigh ...
From $746 per night (USD)
VRBO
From $667 per night (USD)
Expedia
Modern Luxury in Chatham with Water Views: 875-C
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties June rates just reduced! Modern Luxury in Chatham wi ...
From $667 per night (USD)
Expedia
From $799 per night (USD)
VRBO
Near Beach, bike trail, Central AC, WiFi, Private Neighborhood
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
5 Bedroom- 3 Bathroom- Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $799 per night (USD)
VRBO
$North Chatham - Charming \Stones Throw\ (2130)$
From $519 per night (USD)
Expedia
North Chatham - Charming \"Stones Throw\" (2130)
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located outside of downtown Chatham sits this charming four bedroom home, known as Stones Throw. This property features ...
From $519 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Pool Table, Bar, Ping Pong, Sun Rm, Deck,4 BR, Private
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This North Chatham 4 BR home with central AC has plenty of room for families to spread out and enjoy a relaxing Chatham ...
From $372 per night (USD)
VRBO
From $692 per night (USD)
Expedia
BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to Vivian's Hideaway! Experience all that Cape Cod has to offer in an amazing indoor and outdoor living space, n ...
From $692 per night (USD)
Expedia
From $530 per night (USD)
VRBO
Perfect couples escape. Close to beaches, great biking & walking & pet friendly.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This open studio apartment is the perfect stay. Privacy, beach proximity, pet friendly and CLEAN. Lots to do and see in ...
From $530 per night (USD)
VRBO
$Apres Sea - Chatham 4 Bedroom w\/ Central AC$
From $1252 per night (USD)
VRBO
Apres Sea - Chatham 4 Bedroom w\/ Central AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Ideal location just minutes to bike trail, beaches and downtown Chatham! This home is represented by Nauset Rental, a l ...
From $1252 per night (USD)
VRBO
From $666 per night (USD)
VRBO
Perfectly located, with central AC. 3BR, sleeps 6-8
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Our house has undergone a complete renovation with all new updates. The house has a complete master suite on the first ...
From $666 per night (USD)
VRBO
From $1001 per night (USD)
Expedia
Reuben Young House: Two 1st Floor King Master Suites. Close to Town & Beaches.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming circa 1820 antique newly renovated. close to downtown Chatham (1.5 miles). Close to Fish Pier, Ryders Cove, Oys ...
From $1001 per night (USD)
Expedia
From $551 per night (USD)
VRBO
Excellent Chatham Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This Chatham beauty is a Newly built cottage which is walking distance to Pleasant Bay and a short drive to town. A per ...
From $551 per night (USD)
VRBO
$CHATHAM WATER FRONT\/VIEW HOUSE FIRST TIME RENTAL$
From $764 per night (USD)
Expedia
CHATHAM WATER FRONT\/VIEW HOUSE FIRST TIME RENTAL
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Perfect vacation spot. Enjoy your vacation on this 3 bedroom 2 bath, Central air conditioned house bordering Emery Lake ...
From $764 per night (USD)
Expedia
From $1102 per night (USD)
VRBO
FIVE BEDROOM-- WATERFRONT RETREAT ON RYDERS COVE, PERFECT SPOT TO KAYAK AND CANOE.
Bedrooms:
5
Bathrooms:
5
Sleeps:
13
Enjoy this Special Waterfront Retreat on Ryders Cove, a Perfect Spot to Kayak or Canoe! This 5 bedroom, 3.5 bath home ...
From $1102 per night (USD)
VRBO
$Centrally located home with patio, a\/c included, walking distance from town.$
From $656 per night (USD)
Expedia
Centrally located home with patio, a\/c included, walking distance from town.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Centrally located vacation home with central air conditioning in an ideal location with 3 bedrooms, 2 full baths plus ...
From $656 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Three Bedroom Updated Home -- Just Minutes to Pleasant Bay, Town and Bike Path!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sun Filled, Completely Renovated 3 Bedroom, 2 Bath. Minutes from Pleasant Bay or Downtown, Perfect for your Cape Adven ...
From $486 per night (USD)
VRBO
From $1695 per night (USD)
Expedia
Chatham Landmark Estate, Large Guest House, Pool 177-CF
Bedrooms:
8
Bathrooms:
8
Sleeps:
18
This property is professionally managed by Pretty Picky Properties Chatham Landmark Estate, Awesome Barn/Guest House, P ...
From $1695 per night (USD)
Expedia
From $377 per night (USD)
VRBO
On Goose Pond Pet Friendly Wifi Water Views Private
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 Bedroom- 1 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $377 per night (USD)
VRBO
From $893 per night (USD)
VRBO
Lover's Lake Escape - Chatham Lakefront home with private access to Lover's Lake
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This home is represented by Nauset Rental, a local vacation rental management company. Enjoy the serenity of Lover's L ...
From $893 per night (USD)
VRBO
From $777 per night (USD)
VRBO
Sand Dunes and Salty Air - 5 minutes drive to beaches!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A beautiful house on a quiet cul-de-sac that is close to everything that Chatham has to offer. It is less than 2 miles f ...
From $777 per night (USD)
VRBO
From $412 per night (USD)
VRBO
Pondfront cottage on Stillwater Pond
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Set your clocks back 50 years, and fish for your breakfast from your own dock or row-boat. This setting has been descri ...
From $412 per night (USD)
VRBO
From $766 per night (USD)
VRBO
Lake front, Near Beach, AC, WiFi, Pet Friendly near Bike Path
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
3 Bedroom - 2.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $766 per night (USD)
VRBO
From $306 per night (USD)
VRBO
Walk to School House Pond in Chatham.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2500sq ft house is 8yrs old and offers all the toys including a hot tub, sauna, bikes and kayaks for guest use. Fro ...
From $306 per night (USD)
VRBO
From $1075 per night (USD)
VRBO
Charming Waterfront House in Chatham
Bedrooms:
4
Bathrooms:
6
Sleeps:
11
Very private lakefront setting with spectacular views and private beach. Filled with Charm. It was the original Ice Hous ...
From $1075 per night (USD)
VRBO
From $928 per night (USD)
VRBO
Chatham rental, 4 bed 3ba ~ walk to the beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
WALK TO JACKKNIFE COVE BEACH in Chatham from this charming, clean, and well-kept home. Enjoy s'mores with the kids at ou ...
From $928 per night (USD)
VRBO
From $504 per night (USD)
VRBO
Beautiful home near Jacknife Beach and bike trail
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This newly renovated home has 3 bedrooms and 2 1/2 baths,and is located in a nice quiet neighborhood. This home is centr ...
From $504 per night (USD)
VRBO
Click For Pricing
Expedia
Stylish Cape in North Chatham ~ Walk to Private Neighborhood Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautiful cape in upscale Harbor Cove neighborhood. Recently renovated with all new furnishings and appliances. 4 BRs, 2 ...
Click For Pricing
Expedia
From $361 per night (USD)
VRBO
Pet friendly home with central air (1998)
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This adorable PET FRIENDLY cape style home is located on a peaceful, residential, dead end road, close to two fresh wate ...
From $361 per night (USD)
VRBO
$Large Home w\/ Fire Pit and Dogs Welcome!$
From $389 per night (USD)
Expedia
Large Home w\/ Fire Pit and Dogs Welcome!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: 16674 - Heatherwood Haven: Large Home w/ Fire Pit and Dogs Welcome! The Space: Escape to Chatham, where baysid ...
From $389 per night (USD)
Expedia
From $938 per night (USD)
VRBO
THE CHATHAM TREEHOUSE 7 minutes from the Village
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to the Treehouse, just 7 mins from the village of Chatham! This beautiful, private property is nestled in the wo ...
From $938 per night (USD)
VRBO
From $382 per night (USD)
Expedia
Bright home walking distance to Main Street with great patio, firepit & bikes
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Queen Anne Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $382 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Inviting apartment with patio, full kitchen, & golf nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Reynard's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $274 per night (USD)
VRBO
From $531 per night (USD)
Expedia
Gorgeous Home with Game Room Dog Welcome!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: 16675 - Summer Stunner: Gorgeous Home with Game Room Dog Welcome! The Space: Another Cape Cod vacation means a ...
From $531 per night (USD)
Expedia
From $659 per night (USD)
VRBO
WATERFRONT home close to Downtown Chatham!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Soak up the sun while enjoying the lush outdoor space at our waterfront home, Queen’s Quarters. Bring or rent a kayak or ...
From $659 per night (USD)
VRBO
$Chatham Getaway w\/ Trail Access, 2 Mi to Beaches!$
From $415 per night (USD)
Expedia
Chatham Getaway w\/ Trail Access, 2 Mi to Beaches!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Your next Cape Cod adventure awaits at this cozy Chatham vacation rental. Perfect for a memorable family getaway on the ...
From $415 per night (USD)
Expedia
From $473 per night (USD)
VRBO
Cozy cottage in delightful country side neighborhood!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this cozy three-bedroom, two-bath cottage nestled in a peaceful countryside neighborhood. With central air, hi ...
From $473 per night (USD)
VRBO
From $300 per night (USD)
Expedia
Bright cape cod retreat; steps to White pond, bike path, CAC & fire pit
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunny-Side Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $300 per night (USD)
Expedia
From $589 per night (USD)
VRBO
3-bedroom house in charming Chatham with WiFi, fitness room, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 3-bedroom house in Chatham is perfect for your escape to relaxation. With 1 king bed, 1 queen bed, and 4 twin beds, ...
From $589 per night (USD)
VRBO
From $259 per night (USD)
Expedia
New listing! Cozy, fresh and clean 1-bedroom cottage with Pond access in Chatham
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This cozy 1-bedroom cottage in Chatham is the perfect retreat for a couple’s or solo getaway. 2 occupants only please. S ...
From $259 per night (USD)
Expedia
From $1530 per night (USD)
VRBO
Vintage 1730 Farmhouse
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This vintage farm style home built in 1730 has 4 bedrooms (3 kings, 1 queen) and 4 bathrooms and a den that has a trundl ...
From $1530 per night (USD)
VRBO
From $953 per night (USD)
VRBO
Family Friendly Home. Kid Amenities. Beach Nearby!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Perfect for families, this cozy vacation home is packed with kid-friendly amenities! Enjoy a lovely deck, two spacious l ...
From $953 per night (USD)
VRBO
From $1123 per night (USD)
VRBO
Luxurious Home with Pool & Game Room in Cape Cod
Bedrooms:
5
Bathrooms:
4
Sleeps:
11
Welcome to our newly listed vacation home in Chatham, Cape Cod! This spacious 4-bedroom/4.5-bathroom house is a haven fo ...
From $1123 per night (USD)
VRBO
From $917 per night (USD)
Expedia
Pet friendly home with large backyard!
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Enjoy your Chatham vacation at this spacious, 5 bedroom, 2 bath home. Offering 2 queens, a bunk bed and 4 twins, and a t ...
From $917 per night (USD)
Expedia
From $598 per night (USD)
VRBO
Dog-friendly home with yard, patio, grill, & fireplace - great location
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Whale's Tales Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $598 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
2 Bedroom- 2 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $447 per night (USD)
Expedia
Click For Pricing
VRBO
Spacious and beautiful home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beautiful and welcoming property for a group of family or friends looking to have a wonderful time. Quiet and peaceful ...
Click For Pricing
VRBO
From $645 per night (USD)
Expedia
Updated 6 Bedroom Home Close to Everything!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Cranberry Corners is the perfect house for your extended family vacation! DOGS WELCOME! Plenty of space to spread out, ...
From $645 per night (USD)
Expedia
From $1083 per night (USD)
VRBO
Located in quiet Riverbay directly on the river; kayak to Jacknife Beach
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Located in quiet Riverbay neighborhood. This 5 bedroom, 4 bath home that sleeps 10. Plenty of room to spread out with ...
From $1083 per night (USD)
VRBO
From $864 per night (USD)
Expedia
Views of Eastward Ho Golf Course from the backyard!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
North Chatham gem offers views of Eastward Ho Golf Course from the backyard! Antique Cape style home that sleeps 8 peopl ...
From $864 per night (USD)
Expedia
From $997 per night (USD)
VRBO
KAYAK TO PLEASANT BAY FROM YOUR BACK YARD! KAYAKS PROVIDED!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
***KAYAK TO PLEASANT BAY FROM YOUR BACK YARD! KAYAKS PROVIDED! OPEN YEAR ROUND Spacious five bedroom, four bath ho ...
From $997 per night (USD)
VRBO
Click For Pricing
Expedia
The Rose Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to the enchanting Rose Cottage, a hidden gem nestled in the heart of Chatham, Massachusetts. This picturesque re ...
Click For Pricing
Expedia
From $1024 per night (USD)
VRBO
Wonderful dog-friendly rental close to downtown Chatham and Oyster Pond Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Wonderful dog friendly rental for the whole family, with access path to a private beach deeded at White's Pond! Close to ...
From $1024 per night (USD)
VRBO
From $2458 per night (USD)
Expedia
PRIVATE HEATED POOL!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Private Heated pool! Vacation near the beach in this charming 4 bedroom (King/king/queen/queen) and 3.5 bath (3rd bathro ...
From $2458 per night (USD)
Expedia
From $881 per night (USD)
VRBO
Chatham Compound + Carriage House - Huge yard, Game Room, Kayaks, Sleeps 10
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Newly Listed to VRBO. Also listed on Airbnb, with 37 reviews and a 4.97 star rating! This beautiful family home is ever ...
From $881 per night (USD)
VRBO
$Waterfront on Pond w\/ Private Beach!$
From $697 per night (USD)
Expedia
Waterfront on Pond w\/ Private Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: 16664 - Family Tides: Waterfront on Pond w/ Private Beach! The Space: This beautiful waterfront property, loca ...
From $697 per night (USD)
Expedia
Click For Pricing
VRBO
Spacious Cape - Large Private Backyard, 3 Decks!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
All bathrooms and kitchens recently renovated. Fast 1GB internet, full cable, multiple living areas, work from home frie ...
Click For Pricing
VRBO
From $780 per night (USD)
Expedia
Perfect Chatham Retreat | Access To Lovers Lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
*Cancellation policy at end of property description.* Enjoy your best days of summer at this 2BR + Bonus custom home ...
From $780 per night (USD)
Expedia
From $2678 per night (USD)
VRBO
Chatham Gem with Pool & High-End Style RPAM104
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
NEW FOR THE 2025 SEASON! Welcome to your perfect Cape Cod getaway in the heart of Chatham! This stunning 4-bedroom, 3.5- ...
From $2678 per night (USD)
VRBO
From $644 per night (USD)
Expedia
Like new with nautical theme!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Modern nautical-themed decor abounds in this newly renovated, freshly painted Cape located in West Chatham. On a quiet ...
From $644 per night (USD)
Expedia
From $369 per night (USD)
VRBO
AFFORDABLE, COMFORTABLE HOME WITH CENTRAL AIR CONDITIONING!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cozy, comfortable home just short drive to town and beaches. This Chatham 3 bedroom, 2 bath offers central air conditio ...
From $369 per night (USD)
VRBO
From $1292 per night (USD)
Expedia
Royal Retreat: 935-C Renovated Luxury Chatham Home with Pool & Hot Tub
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Renovated Luxury Chatham Home with Pool & Hot Tub Ho ...
From $1292 per night (USD)
Expedia
From $760 per night (USD)
VRBO
Beautiful Chatham
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This property is located in the Ryder's Cove area of Chatham MA. The main house consist of 2 bedrooms on the upper leve ...
From $760 per night (USD)
VRBO
From $893 per night (USD)
VRBO
Robin's Nest - Dog Friendly Chatham 4 Bedroom
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This home is represented by Nauset Rental, a local vacation rental management company. Beautiful, spacious 4 bedroom, 2 ...
From $893 per night (USD)
VRBO
From $1115 per night (USD)
VRBO
Chatham Vacation Rental With Pool and Charm to Spare! RPAM096
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Located in one of Cape Cod’s premier resort towns, 764 Riverview Drive offers everything a discerning vacationer is look ...
From $1115 per night (USD)
VRBO
From $765 per night (USD)
Expedia
A short drive brings you to Jackknife Cove!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy your vacation at this charming and cozy, 3 bedroom, 2 bath home. Offering 2 queens, 2 twins, and a king. Enjoy you ...
From $765 per night (USD)
Expedia
From $1880 per night (USD)
VRBO
Large, beautiful home with extraordinary design features and bonus rooms galore
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This large, gorgeous home is perfect for entertaining, set on an acre of land with a private yard and large patio. The h ...
From $1880 per night (USD)
VRBO
Click For Pricing
Expedia
Chatham pond access with view
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy our large back yard and private road that leads to the Pond behind the house, for fishing, non-motor boating, padd ...
Click For Pricing
Expedia
From $990 per night (USD)
VRBO
5 Bedroom Chatham Charmer RPAM012
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Located in the highly desirable town of Chatham, this five bedroom, three bath rental home will meet all your vacation n ...
From $990 per night (USD)
VRBO
$Large Chatham Rental w\/ 5 Bedrooms w\/ 5 Private Bathrooms RPAM007$
From $1218 per night (USD)
Expedia
Large Chatham Rental w\/ 5 Bedrooms w\/ 5 Private Bathrooms RPAM007
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
This stunning rental home is a vacationer’s dream! Easy and close access to the ponds, bike trails, conservation area a ...
From $1218 per night (USD)
Expedia
From $1138 per night (USD)
VRBO
Gorgeous, Modern, Dog Friendly Chatham 4 Bedroom with Central AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This home is represented by Nauset Rental, a local vacation rental management company. Gorgeous, modern beach house out ...
From $1138 per night (USD)
VRBO
From $1396 per night (USD)
Expedia
Waterfront Renovated Home with Pool and Dock: 560-C
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Waterfront Renovated Home with Pool and Dock Sleeps 8 Rents Friday - Friday during peak season Pets Considered Pool ope ...
From $1396 per night (USD)
Expedia

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Results: 90 Rentals