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From $619 per night (USD)
VRBO
.5 miles to the Beach. Close to Wequasset. Foosball & Kid Friendly Amenities!
Bedrooms:
2
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 $619 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Sweeping Views, 150 Yards to Private Beach!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: 16694 - Oceanside Delight: Sweeping Views, 150 Yards to Private Beach! The Space: Escape to Oceanside Delight, ...
From $626 per night (USD)
Expedia
From $990 per night (USD)
VRBO
Shore Daze: 096-C Luxury Living in Chatham with Pool and Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties Luxury Living in Chatham with Pool and Hot Tub Pool ...
From $990 per night (USD)
VRBO
From $269 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 $269 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Waterfront 3-BR House w Hot tub: kayak/canoe up the tidal river to Pleasant Bay!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Get ready to relax in this 3-bedroom house in Chatham. This wonderful riverfront property features a 7-person hot tub wi ...
From $436 per night (USD)
VRBO
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Expedia
Oar'asis: 093-C Charming Newly Renovated Retreat in Chatham
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties. Charming Newly Renovated Retreat in Chatham NEW Li ...
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Expedia
From $1023 per night (USD)
VRBO
Unique Private Chatham Getaway with Lap Pool & Deck Lounge (2403)
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to your perfect Chatham retreat—new to the rental market and truly one-of-a-kind. Built right into a hillside, t ...
From $1023 per night (USD)
VRBO
From $1292 per night (USD)
Expedia
Coastal Retreat Minutes from Hardings Beach!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Coastal retreat in West Chatham - Minutes from Hardings Beach! Escape to this stunning, recently renovated beach house n ...
From $1292 per night (USD)
Expedia
From $511 per night (USD)
VRBO
Chatham Vineyard View
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to this cozy three-bedroom, two-bath cottage nestled on a private cul-de-sac. A bright and sunny sunroom adds ter ...
From $511 per night (USD)
VRBO
From $820 per night (USD)
VRBO
Chatham Charm Awaits - Family-Friendly Cottage Near Beaches & Local Attractions
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Escape to this delightful cottage nestled in picturesque Chatham—your perfect home base for Cape adventures! With 3 comf ...
From $820 per night (USD)
VRBO
From $840 per night (USD)
VRBO
Spacious Lakefront Escape - Perfect for Families
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Welcome to our spacious lakefront home, perfect for families and large groups! With two master suites, four additional b ...
From $840 per night (USD)
VRBO
From $642 per night (USD)
Expedia
Classic Cape, Walk to Red River Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 17761 - Beach Talk: Classic Cape, Walk to Red River Beach! The Space: Unwind in the heart of Cape Cod at this ...
From $642 per night (USD)
Expedia
From $393 per night (USD)
VRBO
Chatham Pond Side Cottage 2-bedroom with AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Amazing getaway with a delightful blend of comfort and convenience. Imagine the tranquil beauty of a nearby pond unfoldi ...
From $393 per night (USD)
VRBO
From $899 per night (USD)
VRBO
Walk to town and beach from this updated 3BR house in historic Chatham
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Recently renovated for 2025 to include updated bathrooms and new furnishings. NEW photos coming soon! A fantastic, famil ...
From $899 per night (USD)
VRBO
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VRBO
Pleasant Street Hideaway!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to the beauty of Cape Cod in this cozy 3-bedroom, 3-bathroom cottage, just a short stroll from Pleasant Street Be ...
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VRBO
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Expedia
Bright, dog-friendly property located close to Jackknife Beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This bright, dog-friendly rental features a fenced yard and is conveniently located near Jacknife Beach. The property in ...
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Expedia
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VRBO
Charming Coastal Haven in Chatham
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 bedrooms- 2.5 Bathrooms- Sleeps 8 During peak summer weeks, it is typical for our properties to require a 7-night stay ...
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VRBO
From $592 per night (USD)
Expedia
Peaceful beach retreat: private yard, close to beaches, Chatham & rail trail
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sail Away Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $592 per night (USD)
Expedia
From $462 per night (USD)
VRBO
Harwich retreat • Pleasant Bay • HOT TUB • Fire Pit • AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Prime spot on a quiet Harwich lane, five minutes to Pleasant Bay and Chatham center. Walk to Dunkin’ for coffee, pedal a ...
From $462 per night (USD)
VRBO
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Expedia
Charming 4-bedroom house with fresh water dock & shark-free swimming!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to this enchanting house in Chatham. This phenomenal home has been completely renovated over the past few years ...
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Expedia
From $598 per night (USD)
VRBO
Mooncusser Cottage on Taylor's Pond!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Mooncusser! Fabulous two bedroom (1 king, 2 doubles) with a den (sleep sofa) waterfront cottage on saltwater ...
From $598 per night (USD)
VRBO
From $514 per night (USD)
Expedia
Bright & Cozy Harwich Getaway near Beach & Trails
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Nestled on a peaceful cul-de-sac in Harwich, this stylish Cape home welcomes you with a sun-drenched deck, BBQ grill, an ...
From $514 per night (USD)
Expedia
From $554 per night (USD)
VRBO
500 ft to the Beach. Walk to Sand, Sun & Surf!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Looking for the perfect summer getaway? This inviting, clean Cape Cod cottage is just 500 feet from Nantucket Sound’s wa ...
From $554 per night (USD)
VRBO
From $502 per night (USD)
VRBO
Spacious Cape Escape Near Rail Trail & Downtown
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: Spacious home in Chatham sleeps 10 and features a fully renovated kitchen, large dining areas, multiple smart T ...
From $502 per night (USD)
VRBO
From $479 per night (USD)
VRBO
Summer Retreat: 036-C Unique Modern Chatham Home, Walk to Town and Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This property is professionally managed by Pretty Picky Properties Unique Modern Chatham Home, Walk to Town ...
From $479 per night (USD)
VRBO
From $591 per night (USD)
Expedia
Private Beach, Water Views, Incredible Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: 16695 - Tide's Edge: Private Beach, Water Views, Incredible Location! The Space: Welcome to Tide's Edge, a ser ...
From $591 per night (USD)
Expedia
From $925 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 $925 per night (USD)
VRBO
From $327 per night (USD)
VRBO
Private Pool Near Pleasant Bay Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
NEW LISTING - Cozy Cottage, Air Conditioning, Private Pool, Under 300 Steps to Pleasant Bay Beach Within one of South O ...
From $327 per night (USD)
VRBO
From $1961 per night (USD)
VRBO
Nautical retreat with water views, inground heated pool, and private beach access
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
5 Bedroom - 5.5 Baths - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. C ...
From $1961 per night (USD)
VRBO
From $1813 per night (USD)
Expedia
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Charming 5-Bedroom Home in the Heart of Downtown Chatham – Walk to Beach, Shops & More Welcome to your perfect Cape Cod ...
From $1813 per night (USD)
Expedia
From $550 per night (USD)
VRBO
Pet Friendly Waterfront Overlooking Oyster River
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Breezes and Views on Oyster River! Relax in the sun and enjoy the views of the water from the deck of this quintessentia ...
From $550 per night (USD)
VRBO
From $1070 per night (USD)
Expedia
All-New Coastal Luxury Near CBI & Beaches, Dog-Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious, newly renovated home off Shore Rd. Steps to Chatham Bars Inn, Fish Pier, Cow Yard Beach, Veterans Field, and ...
From $1070 per night (USD)
Expedia
From $2019 per night (USD)
VRBO
Large Chatham Home Overlooking the Atlantic
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Enjoy all Cape Cod has to offer with this beautiful sea captain's house centrally located in Chatham, MA. Less than 1 mi ...
From $2019 per night (USD)
VRBO
From $524 per night (USD)
Expedia
North Chatham Retreat – Renovated 3BR, 3.5BA + Bonus, 2900 Sq Ft
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Your North Chatham Retreat – A Perfect Cape Cod Getaway Located in scenic North Chatham and just minutes fro ...
From $524 per night (USD)
Expedia
From $184 per night (USD)
VRBO
Captain Ellis Antique Home in Harwich Port, Cape Cod, MA - 1 Room Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to a charming antique home in Harwich Port. My home was built by Captain James Monroe Ellis in 1862 and is locate ...
From $184 per night (USD)
VRBO
From $781 per night (USD)
VRBO
5-bedroom Cape with a pool and yard games.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Five-bedroom and three-bath Cape style home with large fenced backyard and an inground pool. Various yard games are avai ...
From $781 per night (USD)
VRBO
From $1414 per night (USD)
VRBO
Beautiful Chatham Home, Walk to Beach and Town
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Located in the charming coastal town of Chatham, this incredible property offers the perfect blend of comfort and style ...
From $1414 per night (USD)
VRBO
From $95 per night (USD)
Expedia
Chatham Retreat – 2-Month Minimum, Seasonal & Off-Season Stays RPAM117
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the charm of Cape Cod in this fully furnished 1-bedroom, 1.5-bath condo in sought-after North Chatham. With a ...
From $95 per night (USD)
Expedia

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Chatham Rentals

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Results: 638 Rentals