Chatham Rentals
- From $3000 per night (USD)
VRBO
Waterfront. Private beach. Pool. Estate has it all!!
- Bedrooms:
- 7
- Bathrooms:
- 9
- Sleeps:
- 19
Chosen by Cape Cod Life magazine as one of the Top Ten places to stay on Cape Cod. Our waterfront estate now has a gorg ...
From $3000 per night (USD)VRBO
- From $971 per night (USD)
VRBO
Former B&B in the Heart of Chatham. Sleeps 14, Walk to Beach and Town: 407-C
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 14
This property is professionally managed by Pretty Picky Properties Family Compound in the Heart of Chatham. Sleeps 14, ...
From $971 per night (USD)VRBO
- From $358 per night (USD)
VRBO
Lovely Harwich Home Near Red River Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This lovely, well appointed and recently updated home is located in a quiet area with beautiful Red River Beach on Nantu ...
From $358 per night (USD)VRBO
- From $1043 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 $1043 per night (USD)VRBO
- From $220 per night (USD)
VRBO
Lovely Home Near Bike Path Dog Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16665 - Summer Breeze: Lovely Home Near Bike Path Dog Welcome! The Space: This lovely four bedroom vacation ho ...
From $220 per night (USD)VRBO
- From $429 per night (USD)
Expedia
Walk to private beach, central air, wifi, 3 bedrooms.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Smell the water! Fully renovated, three bedroom, two bathroom Nantucket style home. Walk to private beach on a dead end ...
From $429 per night (USD)Expedia
- From $320 per night (USD)
VRBO
South Orleans Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Launch your canoe or kayaks across the street at Town Landing/Quanset Pond! This 2 bedroom 1.5 bath two-level property ...
From $320 per night (USD)VRBO
- From $722 per night (USD)
VRBO
Main House plus Guest House, Walk to Beach & Village: 086-C
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
This property is professionally managed by Pretty Picky Properties Main House plus Guest House, Walk to Beach & Village ...
From $722 per night (USD)VRBO
- From $129 per night (USD)
VRBO
1\/4 MILE TO BEAUTIFUL RIDGEVALE BEACH.....AND PET FRIENDLY!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
For those that love the beach, this 2 bedroom, 1 bath cottage is perfect: just 1/4 mile walk to Ridgevale beach! Bring ...
From $129 per night (USD)VRBO
- From $640 per night (USD)
VRBO
Ocean views, path to beach, short walk to lighthouse and town, sleeps 12
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
This listing combines a large house having a deck with a beautiful view of the ocean and an adjacent cottage allowing fo ...
From $640 per night (USD)VRBO
- From $617 per night (USD)
VRBO
Beautiful Harwich home with large yard near Red River Beach & Main Street fun
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Skinequit Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $617 per night (USD)VRBO
- From $423 per night (USD)
Expedia
Stylish coastal getaway with dual living areas - walk to Main Street, near beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Chatham Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $423 per night (USD)Expedia
- Click For Pricing
Expedia
Pleasant Bay gem with all-new beds & linens, game room & big deck - near beaches
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Pleasant Bay Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
Click For PricingExpedia
- From $799 per night (USD)
VRBO
Charming Waterfront Home with Commanding Views of Pleasant Bay
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
This 6-bedroom 3.5-bathroom home is the perfect setting for two families or multi-generation families vacationing togeth ...
From $799 per night (USD)VRBO
- From $405 per night (USD)
VRBO
Sunny Updated Chatham Village 2 Bedroom Condo W\/ Large Private Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Fantastic location! Thoughtfully updated with all new furnishings! Beautiful light filled 2 bedroom, 2 bath second floo ...
From $405 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful, cozy ranch home w\/ a deck - walking distance to Downtown Chatham
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
B By the Sea Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
Click For PricingExpedia
- From $375 per night (USD)
VRBO
Classic Cape Cod home near beaches with yard, patio & outdoor fireplace
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Pleasant Bay Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $375 per night (USD)VRBO
- From $359 per night (USD)
Expedia
Charming home on half-acre - near Red River Beach & Cape Cod Rail Trail
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Red River Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $359 per night (USD)Expedia
- From $434 per night (USD)
VRBO
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 $434 per night (USD)VRBO
- From $416 per night (USD)
Expedia
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming Downtown Chatham Condo Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $416 per night (USD)Expedia
- From $603 per night (USD)
VRBO
Waterfront house on Bucks Creek Marsh with deck, dock, & kayaks
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Cape Springs Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $603 per night (USD)VRBO
- From $1480 per night (USD)
Expedia
Beachfront on Pleasant Bay!!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Waterfront! Enjoy your Chatham vacation at this stunning, newly redecorated 5 bedroom 4 and 1 half bath home in North Ch ...
From $1480 per night (USD)Expedia
- From $236 per night (USD)
VRBO
Step back in time in this beautifully maintained antique horse barn cottage!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step back in time in this beautifully maintained antique carriage house that sleeps 5. Beamed ceilings, wide plank floor ...
From $236 per night (USD)VRBO
- From $171 per night (USD)
Expedia
Sweet clapboard cottage that is walk to the beach and downtown!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Spend your vacation in The Sea Crest! This sweet clapboard cottage on the hill off Stage Harbor Road offers an open kitc ...
From $171 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- From $1405 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 $1405 per night (USD)Expedia
- From $148 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 $148 per night (USD)VRBO
- From $129 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 $129 per night (USD)Expedia
- From $357 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 $357 per night (USD)VRBO
- From $1068 per night (USD)
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 ...
From $1068 per night (USD)Expedia
- From $200 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 $200 per night (USD)VRBO
- Click For Pricing
VRBO
Nestled in the woods overlooking horse paddock, yet 3 miles to the beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in a quiet neighborhood in East Harwich, my home abuts Harwich conservation land, and a state park, with beautif ...
Click For PricingVRBO
- From $388 per night (USD)
VRBO
Charming 3b\/2ba House Close to Downtown\/Pier\/Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming 3 bdrm/2ba House -1 mile from Downtown- Close to Lighthouse Beach About our space Pack your bags and leave th ...
From $388 per night (USD)VRBO
- From $760 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 $760 per night (USD)VRBO
- From $870 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 $870 per night (USD)VRBO
- From $408 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 $408 per night (USD)VRBO
- From $651 per night (USD)
VRBO
Beautiful and Spacious, Sleeps 10 and a Quick Walk to Chatham's popular Harding's Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Newly Reduced $750 to $6750 / week for remaining July & August in-season weeks - Book Now Spacious Updated Home, V ...
From $651 per night (USD)VRBO
- From $119 per night (USD)
Expedia
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 $119 per night (USD)Expedia
- From $267 per night (USD)
VRBO
Serene home near downtown with furnished deck - walk to Ridgevale Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy Cape Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $267 per night (USD)VRBO
- From $394 per night (USD)
Expedia
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 $394 per night (USD)Expedia
- From $343 per night (USD)
VRBO
Newly Renovated Modern Pond Access!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16622 - The Yachtsman: Newly Renovated Modern Pond Access! The Space: Fully updated and modernized, this vacat ...
From $343 per night (USD)VRBO
- From $550 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 $550 per night (USD)VRBO
- From $323 per night (USD)
VRBO
Avoid Buyers Remorse, Book Your Fall 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 $323 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $281 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 $281 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $317 per night (USD)
VRBO
Idyllic Cape House Close to Beaches
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Idyllic cape house close to beaches and ponds, as well as walking distance to restaurants, bars, ice cream, and shops in ...
From $317 per night (USD)VRBO
- From $750 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 $750 per night (USD)VRBO
- From $655 per night (USD)
VRBO
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 $655 per night (USD)VRBO
- From $966 per night (USD)
Expedia
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 $966 per night (USD)Expedia
- From $455 per night (USD)
VRBO
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 $455 per night (USD)VRBO
- From $850 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 $850 per night (USD)VRBO
- From $714 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 $714 per night (USD)VRBO
- From $209 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 $209 per night (USD)VRBO
- Click For Pricing
Expedia
Secluded hilltop home at Chatham, with a fenced yard, Pet\/family\/work-friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
*** New Installed Ductless Mini Split heating/AC System *** Nestled atop a secluded hill overlooking the picturesque Mon ...
Click For PricingExpedia
- From $499 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 to the water!) with ...
From $499 per night (USD)VRBO
- From $571 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 $571 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Chatham Beach Cottage + loft Walk to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $300 per night (USD)VRBO
- From $1538 per night (USD)
VRBO
Renovated Luxury Chatham Home with Pool & Hot Tub: 935-C
- 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 $1538 per night (USD)VRBO
- From $500 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 $500 per night (USD)VRBO
- From $1109 per night (USD)
VRBO
Gorgeous Cape Cod getaway with patio, grill, sun room, fireplace, AC, & W\/D
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Deer Meadow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $1109 per night (USD)VRBO
- From $730 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 $730 per night (USD)VRBO
- From $205 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 $205 per night (USD)VRBO
- From $777 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 $777 per night (USD)Expedia
- From $350 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 $350 per night (USD)VRBO
- From $627 per night (USD)
VRBO
Charming 3 bedroom 2.5 bath with all amenities - 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 $627 per night (USD)VRBO
- From $227 per night (USD)
VRBO
New construction home on quiet, private waterview lot near Pleasant Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
New weeks now open for summer 2023! We will provide an additional $250 discount for singles or couples -- please send a ...
From $227 per night (USD)VRBO
- From $477 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 $477 per night (USD)Expedia
- From $462 per night (USD)
VRBO
Chatham Home ~1 Mi to Downtown & Oyster Pond Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Recently built and only 1 mile from Oyster Pond Beach, this Chatham vacation rental has everything you need for your nex ...
From $462 per night (USD)VRBO
- From $557 per night (USD)
Expedia
Horse Lovers Take Notice!! 3 bedroom Cape located in quiet convenient location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This meticulously maintained Cape is a single family home that contains 1,764 sq ft and was built in 2004. This home co ...
From $557 per night (USD)Expedia
- From $179 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 $179 per night (USD)VRBO
- From $423 per night (USD)
Expedia
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
On over two acres of Oceanfront, 'Bayberry and Seadaisy Cottages at Ridgevale Beach face the temperate waters of Nantuc ...
From $423 per night (USD)Expedia
- From $1079 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 $1079 per night (USD)VRBO
- From $708 per night (USD)
Expedia
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 $708 per night (USD)Expedia
- From $350 per night (USD)
VRBO
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 $350 per night (USD)VRBO
- From $503 per night (USD)
Expedia
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 $503 per night (USD)Expedia
- From $323 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 $323 per night (USD)VRBO
- From $1800 per night (USD)
VRBO
Hilltop Views of Pleasant Bay from this Family Compound, Private Beach and Dock!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Perfectly located on a hilltop with 3.5 acres overlooking Pleasant Bay in South Orleans, this sprawling family home, s ...
From $1800 per night (USD)VRBO
- From $377 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 $377 per night (USD)VRBO
- From $650 per night (USD)
Expedia
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 ...
From $650 per night (USD)Expedia
- From $244 per night (USD)
VRBO
Cape Cod House w\/ Deck & Grill: 2 Mi to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $244 per night (USD)VRBO
- From $1790 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 $1790 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Chatham Beach Facing 2 Bedroom Condo With Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic Chatham location with private association beach only minutes to downtown! White sandy beaches, dining and sho ...
From $350 per night (USD)VRBO
- From $986 per night (USD)
Expedia
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 $986 per night (USD)Expedia
- From $837 per night (USD)
VRBO
Newly Built, Centrally Located 4 Bedroom Home
- 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 $837 per night (USD)VRBO
- From $231 per night (USD)
Expedia
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 $231 per night (USD)Expedia
- From $510 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 $510 per night (USD)VRBO
- From $335 per night (USD)
Expedia
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 $335 per night (USD)Expedia
- From $1252 per night (USD)
VRBO
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 $1252 per night (USD)VRBO
- From $370 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 $370 per night (USD)VRBO
- From $301 per night (USD)
VRBO
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 $301 per night (USD)VRBO
- Click For Pricing
VRBO
Cottage with beautiful marsh view, sleeps 7, walking distance to beach and pond
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Relax in our charming cottage with its spectacular views and ideal location. Great for families, young adults and older ...
Click For PricingVRBO
- From $261 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 $261 per night (USD)VRBO
- From $88 per night (USD)
VRBO
Pleasant Forest Shores #1 S. Chatham: Classic Swedish ''Stuga'' style near beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $88 per night (USD)VRBO
- From $1450 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 $1450 per night (USD)VRBO
- From $457 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 $457 per night (USD)Expedia
- From $329 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 $329 per night (USD)VRBO
- From $523 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 $523 per night (USD)Expedia
- From $400 per night (USD)
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 ...
From $400 per night (USD)VRBO
- From $771 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 $771 per night (USD)Expedia