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

Chatham Rentals

From $772 per night (USD)
VRBO
Rhododendron Cottage – Walk to Cockle Cove
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedroom - 2 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $772 per night (USD)
VRBO
From $884 per night (USD)
Expedia
Perfect beach house to spend your summer days in!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Experience your summer vacation in this bright and airy 2-bedroom, 3-bath beach house. It features two queen bedrooms up ...
From $884 per night (USD)
Expedia
From $1189 per night (USD)
VRBO
Nautical Comfort near Rail Trail
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 $1189 per night (USD)
VRBO
From $406 per night (USD)
VRBO
Relaxing 3br, private yard, walk to beach, close to bike trail and shopping!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Relax and unwind at this charming South Chatham cottage, just a short 0.4-mile walk to Pleasant Street Beach. Set on a l ...
From $406 per night (USD)
VRBO
From $1001 per night (USD)
VRBO
Panoramic Water Views w/ Private Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: 16684 - Deja View: Panoramic Water Views w/ Private Beach! The Space: Find yourself on island time at this ...
From $1001 per night (USD)
VRBO
From $223 per night (USD)
VRBO
Newly renovated house 3 minutes to Wequassett Resort and 7 minutes to CBI.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upo ...
From $223 per night (USD)
VRBO
From $581 per night (USD)
VRBO
Ping-Pong & Backyard: Spacious Chatham Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience beachside bliss when you stay at this 3-bedroom, 3-bath South Chatham vacation rental! The home also features ...
From $581 per night (USD)
VRBO
From $553 per night (USD)
Expedia
Walk to Pleasant St Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Special Pricing Offered for Remaining In-Season Weeks - Book and Save10% Off, $2925 per week, plus fees and taxes ...
From $553 per night (USD)
Expedia
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VRBO
Chatham Tails & Trails!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Charming three-bedroom home in quiet neighborhood! One floor living, this home offers a queen bed in each of the three ...
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VRBO
From $1399 per night (USD)
VRBO
Renovated Chatham Compound on Bike Path, Less Than a Mile to the Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
This newly designed charming Chatham compound can sleep over 10 guests with 2 bedrooms in the main house, 2 bedrooms in ...
From $1399 per night (USD)
VRBO
From $751 per night (USD)
VRBO
Heated Plunge Pool, Game Barn, AC, 5 Min to Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: 16683 - Cherry Blossom: Plunge Pool, Game Barn, AC, 5 Min to Beach! The Space: Experience the charm of Cha ...
From $751 per night (USD)
VRBO
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Expedia
3 BR 2 BA Home in Charming Chatham - Close to Beaches, Town and Lobster Rolls!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 3 BR 2 BA home is perfect for your vacation in delightful Chatham. From June 20th to September 12th 2026, there is ...
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Expedia
From $1033 per night (USD)
VRBO
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 $1033 per night (USD)
VRBO
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VRBO
THREE BEDROOM--MINUTES TO GOOSE POND, PLEASANT BAY AND TOWN.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Comfortable home with quiet setting, just short drive to Downtown Chatham, Two Ponds and Beaches. * * * * See e ...
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VRBO
From $1648 per night (USD)
VRBO
Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to your dream Cape Cod getaway! Our brand-new, fully renovated 4-bedroom, 5-bath luxury home offers breathtaking ...
From $1648 per night (USD)
VRBO
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VRBO
Four Bedroom - Just 6/10's of a Mile to Nantucket Sound Forest Beach
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Charming Four Bedroom, 1.5 Bath Cottage that is just 6/10's of a mile to beautiful Forest Beach. * * * * See en ...
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VRBO
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VRBO
Beautiful and Spacious, 3BR/3 BR with bonus room - walk to the beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Lovely 4-bedroom, 3.5-bath beach rental on a quiet side street, just steps from Harding’s Beach. Light and bright with b ...
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VRBO
From $400 per night (USD)
VRBO
Let your Chatham traditions begin here!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
From the moment you walk into our charming single floor cottage you are invited to relax and unwind. Whether it is coffe ...
From $400 per night (USD)
VRBO
From $1493 per night (USD)
VRBO
Enjoy a Cape Cod beach vacation on the beach in picturesque Chatham.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Have the vacation of your dreams in this oceanfront beach cottage with beautiful water views, located on Morris Island i ...
From $1493 per night (USD)
VRBO
From $754 per night (USD)
VRBO
Newly Renovated Chatham Home overlooking Cranberry Bog.
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Beautiful classic cape house with huge back deck overlooking a quintessential Cape Cod cranberry bog. The house has been ...
From $754 per night (USD)
VRBO
From $2183 per night (USD)
VRBO
Water views, private beach and spectacular sunsets from highest point in town.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This large, beautiful home is the perfect place to stay for your next beach vacation: whether you’re hosting a big group ...
From $2183 per night (USD)
VRBO
From $723 per night (USD)
Expedia
Chatham Bliss - Dog Friendly oasis with EV Charging
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our recently updated getaway in charming Chatham, MA! Our pet-friendly retreat is the perfect destination for ...
From $723 per night (USD)
Expedia
From $1064 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 $1064 per night (USD)
VRBO
From $1202 per night (USD)
Expedia
Large Chatham Rental w/ 5 Bedrooms w/ 5 Private Bathrooms RPAM007
Bedrooms:
5
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 $1202 per night (USD)
Expedia
From $2287 per night (USD)
VRBO
Hiawatha: 177-CC Gorgeous Chatham Estate with heated pool, walk to Town or Beach
Bedrooms:
5
Bathrooms:
7
Sleeps:
15
This home is professionally managed by Pretty Picky Properties Gorgeous Chatham Estate with heated pool, walk to Town o ...
From $2287 per night (USD)
VRBO
From $417 per night (USD)
Expedia
Close to Bike Path 1 Mile to Beaches!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 16673 - Mayflower Retreat: Close to Bike Path 1 Mile to Beaches! The Space: A quick pedal from the Cape Co ...
From $417 per night (USD)
Expedia
From $713 per night (USD)
VRBO
NEW LISTING Peace and Quiet Pond Front
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Watch the sunset Mill Pond. Surrounded by nature the tranquility is perfection. Just minutes to Chatham Light, Cockle Co ...
From $713 per night (USD)
VRBO
From $2582 per night (USD)
Expedia
Elevate Your Cape Stay: Chatham Luxury with Pool & Beach RPAM026
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Located just .9 miles from the Chatham Bars Inn and 1.3 Miles from Main Street, this 6 bedroom 6 full bath luxury home s ...
From $2582 per night (USD)
Expedia
From $1303 per night (USD)
VRBO
Private Beach Front Chatham Rental Close To Everything RPAM054
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Nestled in one of the most coveted areas of Cape Cod, 63 Morris Island Road offers everything a discerning tenant could ...
From $1303 per night (USD)
VRBO
From $414 per night (USD)
VRBO
Dog Friendly Chatham 4 Bedroom, A/C
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: Perfect location near Schoolhouse Pond, Pleasant Bay and downtown Chatham The Space: *Contact us for infor ...
From $414 per night (USD)
VRBO
From $593 per night (USD)
VRBO
Close to Hardings Beach & Private Access to Oyster River
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Comfy and cozy four bedroom home near Hardings Beach! This recently updated Cape cottage is filled with new furnishings, ...
From $593 per night (USD)
VRBO
From $1649 per night (USD)
Expedia
Chatham Charm with Pool and Private Beach RPAM006
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Tucked in the private Cannon Hill Neighborhood, this enchanting 4 bedroom, 3 full and 1 half bathroom home with a large ...
From $1649 per night (USD)
Expedia
From $1830 per night (USD)
VRBO
Royal Retreat: 935-C Renovated Luxury Chatham Home with Pool & Hot Tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Renovated Luxury Chatham Home with Pool & Hot Tub Ho ...
From $1830 per night (USD)
VRBO
From $524 per night (USD)
VRBO
CHARMING 4 BEDROOM HISTORIC PROPERTY, WALK TO TOWN AND LIGHTHOUSE BEACH!!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Close to Town and Lighthouse Beach, Located in the Heart of the Old Village Section of Chatham. * * * * See en ...
From $524 per night (USD)
VRBO
From $2482 per night (USD)
VRBO
Oceanside Chatham / walk to Town, Beaches and CBI
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Our home sits on a double-lot, just a few hundred feet from the Atlantic Ocean, with just an easy walk to Town, Beaches ...
From $2482 per night (USD)
VRBO
From $373 per night (USD)
VRBO
Walk to the warm waters of Nantucket sound 3B/2B home CA, W & D, all amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Three bedroom, two bath home 1/2 mile walk to Ridgevale Beach. Home includes central air, color cable, wi-fi, washer a ...
From $373 per night (USD)
VRBO
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VRBO
Heated pool, hot tub and breathtaking views! RPMS025
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Michelle Sylvia high end collection rental home. Imagine walking through the front door to a stunning view of the Harb ...
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VRBO
From $801 per night (USD)
VRBO
Ideal Chatham Location. Waterview, Beach, Walk to Town,Great Views,4 Bedroom,AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Bright, sun drenched house with ocean views on Two sides. Two outdoor dining areas. All corner bedrooms with window ...
From $801 per night (USD)
VRBO
From $1193 per night (USD)
VRBO
Classic 5Br Cape Cod Home In Exclusive N. Chatham- Steps To The Private Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to the Whydah Figawai - a privately-owned and classic Cape Cod style five bed room vacation home in a quiet & qu ...
From $1193 per night (USD)
VRBO

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Chatham Rentals

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Results: 439 Rentals