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VRBO
Vacation on Library Lane in the heart of downtown Chatham!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Vacation on Library Lane in the heart of downtown Chatham! This newly renovated home that sleeps 8 in 2 queens, 2 twins ...
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VRBO
From $1520 per night (USD)
Expedia
PRIVATE HEATED POOL! Pet friendly, sleeps 9 near the beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Private pool! Vacation near the beach in this charming 4 bedroom (King/king/queen/two twins/a trundle) and 4.5 bath home ...
From $1520 per night (USD)
Expedia
From $244 per night (USD)
VRBO
Cute clapboard cottage on the hill off Stage Island Road!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Spend your vacation in The Sand Dune! This cute clapboard cottage on the hill off Stage Island Road offers an open kitch ...
From $244 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Colorful clapboard cottage perfect for 2!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Spend your vacation in The Sea Glass, a charming clapboard cottage on the hill off Stage Island Road that offers an open ...
From $248 per night (USD)
Expedia
From $524 per night (USD)
VRBO
Just off the Chatham bike loop... a perfect location for your family vacation.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just off the Chatham bike loop, is a perfect location for your family vacation. This two bedroom home offers a queen and ...
From $524 per night (USD)
VRBO
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Expedia
Tastefully appointed new home located at the end of a cul-de-sac!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Tastefully appointed home located at the end of a cul-de-sac with plenty of living area and beautiful outdoor space. Com ...
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Expedia
From $370 per night (USD)
VRBO
The Whistling Whale - Fantastic Location!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Whistling Whale - Fantastic Location!! Charming one bedroom, upstairs apartment with a queen bed and fabulous views ...
From $370 per night (USD)
VRBO
$Charming 3b\/2ba House Close to Downtown\/Pier\/Beach$
From $489 per night (USD)
Expedia
Charming 3b\/2ba House Close to Downtown\/Pier\/Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming 3bdrm/2ba House -1 mile from Downtown- Close to Lighthouse Beach About our space Pack your bags and leave the ...
From $489 per night (USD)
Expedia
From $898 per night (USD)
VRBO
Spacious Home Facing Nantucket Sound
Bedrooms:
5
Bathrooms:
3
Sleeps:
10
Our airy and comfortable beach house features tranquil ocean views, a large 22 x 11 foot elevated back deck, 4 bedrooms, ...
From $898 per night (USD)
VRBO
$Beach Cottage 4BD\/2BATH (2,138 sqft)$
From $858 per night (USD)
VRBO
Beach Cottage 4BD\/2BATH (2,138 sqft)
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Beautifully renovated 4 BR/2BA bath Cape (2,138 sqft) and just a mile from Hardings Beach! Enjoy the updated kitchen, l ...
From $858 per night (USD)
VRBO
From $511 per night (USD)
VRBO
Cozy North Chatham house. Great location, near downtown shopping and fish pier
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
North Chatham house a mile from Chatham fish pier. We are short drive to Lighthouse, Hardings or Ridgevale beach in on ...
From $511 per night (USD)
VRBO
From $755 per night (USD)
Expedia
Beautiful and Spacious, Sleeps 10 and a Quick Walk to Chatham's popular Harding's Beach!
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Spacious Updated Home, Very Close to Popular Kid-friendly Harding's Beach, just Perfect for Two Families! This lovel ...
From $755 per night (USD)
Expedia
$Charming ranch home with fast WiFi, central air conditioning, & a washer\/dryer$
From $417 per night (USD)
VRBO
Charming ranch home with fast WiFi, central air conditioning, & a washer\/dryer
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Jesmond Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $417 per night (USD)
VRBO
From $807 per night (USD)
Expedia
Serene home near downtown with furnished deck - walk to Ridgevale Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Cozy Cape Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $807 per night (USD)
Expedia
From $510 per night (USD)
VRBO
5-Mins to Forest Beach Dog Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 16647 - Pink Sky : 5-Mins to Forest Beach Dog Friendly! The Space: Escape the hustle and bustle of your everyd ...
From $510 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Newly Renovated Modern Pond Access!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: 16622 - The Yachtsman: Newly Renovated Modern Pond Access! The Space: Fully updated and modernized, this vacat ...
From $408 per night (USD)
Expedia
From $776 per night (USD)
VRBO
Perfect Chatham Retreat | Access To Lovers Lake
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
*Cancellation policy at end of property description.* Enjoy your best days of summer at this 2BR + Bonus custom home ...
From $776 per night (USD)
VRBO
From $472 per night (USD)
VRBO
Avoid Renters Remorse, Book Your Next Getaway Now!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Summary: Recently renovated home in Harwich awaits your next groups stay. 3 Bedrooms, 2.5 bathrooms, 5 beds, sleeps 10. ...
From $472 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Breezy beachy house close to everything but away from it all
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Eastpoint – the ultimate vacation rental that strikes the perfect balance between convenience and serenity! T ...
From $574 per night (USD)
VRBO
From $399 per night (USD)
Expedia
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 $399 per night (USD)
Expedia
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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 ...
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VRBO
From $401 per night (USD)
VRBO
Idyllic Cape House Close to Beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Idyllic cape house close to beaches and ponds, as well as walking distance to restaurants, bars, ice cream, and shops in ...
From $401 per night (USD)
VRBO
From $761 per night (USD)
VRBO
Chatham's Best Views-Harbor & Atlantic; On the Beach 4 Kayaks, 2 SUP's, 5 chairs
Bedrooms:
5
Bathrooms:
3
Sleeps:
5
This exquisite ONE (1) family home easily compares favorably to ocean front suites at the Chatham Bars Inn for a fractio ...
From $761 per night (USD)
VRBO
From $658 per night (USD)
Expedia
Sparkling New in Chatham, Superb Views, Walk to Beaches : 041-C
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties. Sparkling Renovation in Chatham, Superb Views, Walk ...
From $658 per night (USD)
Expedia
From $919 per night (USD)
VRBO
Dog Friendly! Half mile to Hardings Beach, newly updated, modern coastal chic, great outdoor space
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
3 Bedroom - 3.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $919 per night (USD)
VRBO
From $635 per night (USD)
Expedia
Charming colonial gem with multiple decks, gas grill, patio, and central AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Chatham Charmer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $635 per night (USD)
Expedia
From $912 per night (USD)
VRBO
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
1.2 acres of beautiful waterfront property. Pond is great for canoes, fishing, and swimming. Canoe provided for tenant u ...
From $912 per night (USD)
VRBO
From $1328 per night (USD)
VRBO
Perfect spot to kayak or 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 $1328 per night (USD)
VRBO
From $245 per night (USD)
VRBO
Renovated cottage 1 mile to beach in Chatham!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Totally renovated bungalow style cottage with a sunny open floor plan, brand new appliances and furnishings on quiet str ...
From $245 per night (USD)
VRBO
From $708 per night (USD)
VRBO
Beautiful Waterfront home, overlooking Pleasant Bay.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
LOCATION! LOCATION! LOCATION! Come to Cape Cod and enjoy this beautiful waterfront home, just steps from the water! With ...
From $708 per night (USD)
VRBO
From $484 per night (USD)
VRBO
In the heart of Chatham Village -- Walk to everything Chatham has to offer.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to our Chatham Bookends (main house) and Pencil Me Inn (guest cottage) tucked away just steps from Chatham Villa ...
From $484 per night (USD)
VRBO
From $410 per night (USD)
VRBO
Chatham Beach Cottage + loft Walk to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax with the whole family at this year round Charming Chatham Seaside Cottage , with just a short 5 minute walk to a b ...
From $410 per night (USD)
VRBO
$Centrally located home with patio, a\/c included, walking distance from town.$
From $558 per night (USD)
VRBO
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 $558 per night (USD)
VRBO
$ABSOLUTELY AMAZING WATER VIEWS OF NANTUCKET SOUND AND JUST 1\/10 OF A MILE WALK TO DEEDED ASSOCIATION BEACH!$
From $955 per night (USD)
VRBO
ABSOLUTELY AMAZING WATER VIEWS OF NANTUCKET SOUND AND JUST 1\/10 OF A MILE WALK TO DEEDED ASSOCIATION BEACH!
Bedrooms:
5
Bathrooms:
5
Sleeps:
11
Just 1/10 of a Mile to Deeded Association Beach! You will never want to leave this property, the views will take your b ...
From $955 per night (USD)
VRBO
From $431 per night (USD)
VRBO
Wrap-Around Porch Mins. to Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: 16643 - Tidal Treasure: Wrap-Around Porch Mins. to Beach! The Space: There isn’t a much more beautiful place t ...
From $431 per night (USD)
VRBO
From $1480 per night (USD)
Expedia
Luxurious Waterfront Home!
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Summary: 15526 - Nautical Dream: Luxurious Waterfront Home! The Space: Orleans, Cape Cod is a picturesque town full of ...
From $1480 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Sun-filled Completely Renovated 3 BR-2B minutes from Pleasant Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sun Filled, Completely Renovated 3 Bedroom, 2 Bath Minutes from Pleasant Bay or Downtown, Perfect for your Cape Adventur ...
From $446 per night (USD)
VRBO
From $829 per night (USD)
VRBO
Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
A charming 3 bedroom, 2.5 bath cape with large kitchen and private backyard, patio and deck that abuts conservation lan ...
From $829 per night (USD)
VRBO
From $300 per night (USD)
VRBO
New construction home on quiet, private waterview lot near Pleasant Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We will provide an additional $250 discount for singles or couples -- please send a message and we'll discuss how to imp ...
From $300 per night (USD)
VRBO
From $595 per night (USD)
Expedia
The Boarding House, Air conditioned King bed comfort
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This completely renovated 4 bedroom cape is about .5 miles from Nantucket Sound beaches. Inside there is central air con ...
From $595 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Chatham Home ~ 1 Mi to Town & Oyster Pond Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Recently built and only 1 mile from Oyster Pond Beach, this Chatham vacation rental has everything you need for your nex ...
From $357 per night (USD)
VRBO
From $315 per night (USD)
VRBO
Exquisite Cottage - Minutes to Village Center and Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome! This cottage is just perfect - it's adorable, fully independent and recently renovated. The cottage is 660 squa ...
From $315 per night (USD)
VRBO
From $309 per night (USD)
VRBO
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
On over two acres of Oceanfront, 'Bayberry and Seadaisy Cottages at Ridgevale Beach face the temperate waters of Nantuc ...
From $309 per night (USD)
VRBO
From $1038 per night (USD)
VRBO
New Waterfront Townhome
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster. Beautifully and meticulously designed, this Town ...
From $1038 per night (USD)
VRBO
From $875 per night (USD)
VRBO
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Ocean Harbor Waterfront. Stunning downtown Chatham Waterfront location with panoramic views, (Little Mill Pond) with ...
From $875 per night (USD)
VRBO
From $436 per night (USD)
Expedia
5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
My family and i live full time in lexington, ma. We decided to purchase a vacation home in chatham, ma because of the sh ...
From $436 per night (USD)
Expedia
$Walk to Beach-Water views-Central A\/C and WiFi$
From $739 per night (USD)
VRBO
Walk to Beach-Water views-Central A\/C and WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedroom- 2 Bathroom- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $739 per night (USD)
VRBO
From $320 per night (USD)
VRBO
Pleasant Chatham Cape
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to Pleasant Chatham Cape, a quintessential Cape Cod house that offers all-season fun in Chatham. This charming h ...
From $320 per night (USD)
VRBO
From $1249 per night (USD)
VRBO
Fabulous Family Capehouse, with Views of Pleasant Bay, with Beach and Dock!
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
AVAILABLE SUN 8/10 to SUN 8/17, 2025! This sprawling family beach home is perfectly located on a hilltop with 3.5 acre ...
From $1249 per night (USD)
VRBO
From $762 per night (USD)
VRBO
Solitude near the beach, High speed wifi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Comfort, convenience and beauty a mere 5 minute stroll away from Ridgevale beach. Nestled in a quiet neighborhood, our b ...
From $762 per night (USD)
VRBO
Click For Pricing
VRBO
Spacious Home on the Loop in Chatham
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Located on the Loop in scenic Chatham, this house rents Sunday to Sunday. The large living room opens onto a deck with ...
Click For Pricing
VRBO
$Cape Cod House w\/ Deck & Grill: 2 Mi to Beach!$
From $337 per night (USD)
Expedia
Cape Cod House w\/ Deck & Grill: 2 Mi to Beach!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
If you’re looking to listen to the ocean waves, hit the greens on a pristine course, and savor fresh-caught seafood in a ...
From $337 per night (USD)
Expedia
From $1840 per night (USD)
VRBO
Location! Pool & Spa! 2 Primary Suites, Walk to Town, Beach, Chatham Bars Inn
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
**As is customary with Cape rentals, there is a cleaning fee and a 14.45% local and state lodging tax. Please enter desi ...
From $1840 per night (USD)
VRBO
From $612 per night (USD)
Expedia
Chatham Beach Facing 2 Bedroom Condo With Private Beach Access (2267)
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic Chatham location with private association beach only minutes to downtown! White sandy beaches, dining and sho ...
From $612 per night (USD)
Expedia
From $1309 per night (USD)
VRBO
Charming and updated home with private gardens and patio!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming and updated home with private gardens and patio! Located on "The Loop", this vacation rental that sleeps 8 is g ...
From $1309 per night (USD)
VRBO
From $1117 per night (USD)
Expedia
Luxury 4 Bedroom Harwich Home - Centrally Located
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Our home is located close to East Harwich shopping centers, restaurants, and Pleasant Bay for boating, fishing, and swim ...
From $1117 per night (USD)
Expedia
From $534 per night (USD)
VRBO
Serene home with WiFi, deck, & outdoor fireplace - walk to beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Harwich Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $534 per night (USD)
VRBO
From $793 per night (USD)
VRBO
ELBOW INN ,Private Retreat with Two Master Suites
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This fully air conditioned 4 bedroom, 3 bath house on 1/2 acre lot sleeps 8 with 2 master suites! The main house has 3 b ...
From $793 per night (USD)
VRBO
From $326 per night (USD)
VRBO
Deeded Rights to Emery Pond Fire Pit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 16646 - Sunny-Side-Up: Deeded Rights to Emery Pond Fire Pit! The Space: Spend a week where the sun always shin ...
From $326 per night (USD)
VRBO
From $1674 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 $1674 per night (USD)
Expedia
From $423 per night (USD)
VRBO
Large Yard, Quiet; 300 Yd on Sidewalk to Hardings Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
If you have small children or would just like some peace and serenity, Blue Skye is for you. Lots of lawn to run and pl ...
From $423 per night (USD)
VRBO
From $478 per night (USD)
Expedia
Full Renovation! Amazing Spot with Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: 16620 - A Step Above: Full Renovation! Amazing Spot with Views! The Space: Our completely renovated and newly ...
From $478 per night (USD)
Expedia
From $656 per night (USD)
VRBO
9-Min Walk to Water Fire Pit!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16645 - First Mates Escape : 9-Min Walk to Water Fire Pit! The Space: Spend a week exploring the shores of Cap ...
From $656 per night (USD)
VRBO
From $121 per night (USD)
VRBO
Pleasant Forest Shores #1 S. Chatham: Classic Swedish ''Stuga'' style near beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget w ...
From $121 per night (USD)
VRBO
From $1709 per night (USD)
VRBO
Historic Home With Private Beach On Stage Harbor
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
** Weekly rentals only: Saturday to Saturday ** ** No Pets or Parties** Our family has enjoyed this community for ov ...
From $1709 per night (USD)
VRBO
From $665 per night (USD)
Expedia
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 $665 per night (USD)
Expedia
$Beautiful Home w\/ Artistic Flair!$
From $452 per night (USD)
VRBO
Beautiful Home w\/ Artistic Flair!
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Summary: 16657 - Artist's Haven: Beautiful Home w/ Artistic Flair! The Space: On the Cul-de-sac of a private Chatham ne ...
From $452 per night (USD)
VRBO
$Centrally Located Home w\/ Patio Fire Pit!$
From $567 per night (USD)
Expedia
Centrally Located Home w\/ Patio Fire Pit!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: 16658 - Home Base: Centrally Located Home w/ Patio Fire Pit! The Space: Conveniently situated in the middle of ...
From $567 per night (USD)
Expedia
Click For Pricing
VRBO
North Chatham, Quaint Cottage, Great Yard, Welcome to Bobs Place
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedroom - 1 Bathroom - Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
Click For Pricing
VRBO
From $1151 per night (USD)
Expedia
Bungalow style home in downtown Chatham!
Bedrooms:
3
Bathrooms:
6
Sleeps:
11
Spend your Cape Cod vacation in a large bungalow style home located in the heart of Chatham. Only 1/2 mile to the sandy ...
From $1151 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Quaint 2 Bedroom Cottage Overlooking White Pond
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Must bring your own linens. Perfect getaway to relax and unwind. Located in a small 5 acre enclave of cottages nestled u ...
From $304 per night (USD)
VRBO
From $1183 per night (USD)
VRBO
Location and Luxury
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
LOCATION: The cottage is located in Chatham's old village, just a block from the ocean. The closest beach is Andrew Har ...
From $1183 per night (USD)
VRBO
From $1024 per night (USD)
VRBO
Family friendly luxury home with heated pool and spa
Bedrooms:
5
Bathrooms:
4
Sleeps:
14
Gorgeous home in Chatham with a brand new heated saltwater pool and hot tub. The open floor plan, combined living and ...
From $1024 per night (USD)
VRBO
From $281 per night (USD)
VRBO
Cozy one bedroom on White pond (Must bring your own linens)
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
2 Person only. Charming little classic Cape cottage located close to town, beaches and bike trail. The cottage is nestl ...
From $281 per night (USD)
VRBO
From $788 per night (USD)
VRBO
Refreshed Interior Central AC WIFI Large Yard Deck Great Chatham Location
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
4 Bedroom - 2 Baths - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $788 per night (USD)
VRBO
From $312 per night (USD)
Expedia
Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
South Chatham Sunshine Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $312 per night (USD)
Expedia
From $849 per night (USD)
VRBO
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 $849 per night (USD)
VRBO
From $513 per night (USD)
Expedia
Chatham walk to Cape Cod beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A Very Short Walk to Hardings Beach. Ocean-side private neighborhood. Chosen by Condé Nast Traveler as “One of the Bes ...
From $513 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Charming Downtown Chatham
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Charming in town apartment above retail shops overlooks the Main St. Walk to beaches, nearby shops & restaurants, band c ...
From $285 per night (USD)
VRBO
$Chatham 3 Bedroom\/2 Bath Retreat$
From $315 per night (USD)
Expedia
Chatham 3 Bedroom\/2 Bath Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully renovated and spacious 3 Bedroom 2 Full Bath Home on a private 1/2 acre setting in one of Chatham's sought a ...
From $315 per night (USD)
Expedia
$Lovely Stage Harbor Estate Guest House W\/Private Beach to Use$
From $315 per night (USD)
VRBO
Lovely Stage Harbor Estate Guest House W\/Private Beach to Use
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Lovely guest house on quiet and picturesque Stage Harbor! Right on town way with 30 second walk to the water and use of ...
From $315 per night (USD)
VRBO
From $832 per night (USD)
Expedia
Near beach and town, private, AC, pet friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
3 Bedrooms- 3 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $832 per night (USD)
Expedia
$\Chatham Up\ - Come Stay, Relax, Have Fun!$
From $255 per night (USD)
VRBO
\"Chatham Up\" - Come Stay, Relax, Have Fun!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
"CHATHAM UP" is a wonderful home located in North Chatham within a very established family neighborhood which is great f ...
From $255 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Stunning 3BR Home - Close to Town & Beaches (2159)
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Nestled in East Harwich, this beautiful 3BR/3BA Harwich home features a welcoming open floor plan with high ceilings, ha ...
From $541 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
From $867 per night (USD)
Expedia
CHARMING COASTAL COTTAGE IN NORTH CHATHAM
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
...
From $867 per night (USD)
Expedia
From $792 per night (USD)
VRBO
Charming new 3Bd Rm 4 bath home .6mi to Ridgevale Beach
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Newly built home, app 2900 sq feet, The 1st floor includes a master bedroom with private bath with tub/shower, king siz ...
From $792 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Chatham Break! 3BR, large quiet yard, walk to shops + restaurants.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Traditional Cape Cod style home with a large, private yard, sunny deck, outdoor shower and hammock in a quiet Chatham ne ...
From $444 per night (USD)
Expedia
From $711 per night (USD)
VRBO
New Waterfront Townhome
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachus ...
From $711 per night (USD)
VRBO
From $776 per night (USD)
VRBO
WATER VIEW OF STETSON COVE! UPDATED HOME WITH SO MUCH TO OFFER!
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
Newly Updated Home With Lovely Views Of Stetson Cove! This spacious, immaculate home boasts large kitchen with double ...
From $776 per night (USD)
VRBO
From $887 per night (USD)
VRBO
Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This updated 4-bedroom 2-bathroom home has the best view on Pleasant Bay, hands down. The open floor plan is ideal for l ...
From $887 per night (USD)
VRBO
From $641 per night (USD)
VRBO
Happy Yellow House - Family and pet-friendly; walkable to Ridgevale Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
*Note: The minimum stay dropped to 3 nights for Jan-March! Other months are still 7 nights as a minimum. The monthly dis ...
From $641 per night (USD)
VRBO
$CHATHAM WATER FRONT\/VIEW HOUSE FIRST TIME RENTAL$
From $616 per night (USD)
VRBO
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 $616 per night (USD)
VRBO
From $670 per night (USD)
Expedia
Air Conditioned, King bed Comfort .Dog friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cranberry Cove, beautiful bright open-plan 3 bedroom house with central AC, a great room made for family time, with vaul ...
From $670 per night (USD)
Expedia
From $236 per night (USD)
VRBO
Cozy Cottage close to Beaches, Boating, Biking, Shopping and more
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Centraly located on the elbow of Cape Cod, cozy little cottage in isolated neighborhood of like summer homes. Two bedroo ...
From $236 per night (USD)
VRBO
From $1159 per night (USD)
Expedia
Beachfront, ocean view, pet friendly, sleeps 8 Nauset Watch
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 Bedroom- 2 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $1159 per night (USD)
Expedia
From $556 per night (USD)
VRBO
Secluded Chatham Cape Cod House Stage Harbor Area
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Very secluded 3br family friendly (pets considered) full Cape at the end of a cul-de-sac. Located in rural Stage Harbor ...
From $556 per night (USD)
VRBO
From $372 per night (USD)
VRBO
Fabulous Quiet Cape, Close to Beach, Central Air, Perfect for Families
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy your quiet family get-away in a lovely, newer construction beautifully decorated cape with central air. Just a co ...
From $372 per night (USD)
VRBO
From $459 per night (USD)
VRBO
Cozy Cape near Chatham Center
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
You will be sure to enjoy your time in the idyllic town of Chatham, MA in Cape Cod. Our home is 1/2 mile from the qua ...
From $459 per night (USD)
VRBO
From $493 per night (USD)
Expedia
Relaxing, peaceful area close to beaches, downtown Chatham, and walking trails.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 3 bedroom 2 bathroom two-story Cape is private, quiet, and overlooks a lovely cranberry bog. Living room, dining r ...
From $493 per night (USD)
Expedia

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