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From $891 per night (USD)
VRBO
NEW! Walk 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 $891 per night (USD)
VRBO
From $657 per night (USD)
VRBO
Pondside Retreat - Beach Access, Game Room, Firepit, Spacious Yard & Water Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your perfect Cape Cod getaway for families or a group of friends! This beautiful retreat offers stunning pond ...
From $657 per night (USD)
VRBO
From $993 per night (USD)
VRBO
Spacious 4-bedroom house in Chatham - Walkable to Oyster Bay Pond & Downtown.
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Enjoy the wonders of Chatham in our family's summer home. Located a 2 minute walk from Oyster Bay Pond and 8 minutes fr ...
From $993 per night (USD)
VRBO
From $772 per night (USD)
VRBO
Marsh and Nantucket Sound Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
PETS ALLOWED WITH OWNER APPROVAL ASK US ABOUT OUR FALL SPECIAL PRICING!!! If you love the beach, views of the wate ...
From $772 per night (USD)
VRBO
From $784 per night (USD)
VRBO
Chatham Shenanigans, Chatham Shenanigans
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience the beauty of Cape Cod at Chatham Shenanigans. This beautiful, well-appointed, bright home is centrally locat ...
From $784 per night (USD)
VRBO
From $1812 per night (USD)
VRBO
Downtown Chatham Family Retreat - Spacious Deck, Games & Firepit - Walk to town
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Your family or group of friends will be close to everything when you stay at this centrally-located home. This cozy home ...
From $1812 per night (USD)
VRBO
From $658 per night (USD)
VRBO
NEW LISTING! Perfect family home, short walk to Chatham!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This completely renovated and newly painted home is located on a private road and just a few minutes walk away from all ...
From $658 per night (USD)
VRBO
From $1230 per night (USD)
Expedia
Chatham Oasis: 099-C Renovated Chatham Village Farmhouse, Heated Pool, Walk to Beach & Town
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties. Renovated Chatham Village Farmhouse, Pool, Walk to ...
From $1230 per night (USD)
Expedia
From $467 per night (USD)
VRBO
CHATHAM-OPEN 8/09 & availability 8/30 & beyond! WALK TO BEACHES, SHOPS, DINING!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
CHATHAM - AVAIL SATURDAY 8/09, 8/30 and 8/31. SEPTEMBER and OCTOBER stays are discounted! WALK TO 3 BEAUTIFUL SANDY BE ...
From $467 per night (USD)
VRBO
From $2175 per night (USD)
VRBO
Oyster Pond Waterfront - Chatham, Massachusetts
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Capture spectacular sunrises, seasonal fireworks, and everything in between via the unobstructed panoramic water and tow ...
From $2175 per night (USD)
VRBO
From $1144 per night (USD)
VRBO
Booking for 2025 now! WATERVIEWS! 4min drive to Hardings Beach!
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
We loved seeing the different groups who came through our house this year. We had bachelorette parties, multi-generation ...
From $1144 per night (USD)
VRBO
From $3630 per night (USD)
Expedia
Sophisticated Chatham Oasis with Pool & Spa RPAM062
Bedrooms:
8
Bathrooms:
5
Sleeps:
12
Welcome to 84 Doane Road in Chatham, MA, where opulence meets comfort and convenience. Nestled in a prime location just ...
From $3630 per night (USD)
Expedia
From $1124 per night (USD)
VRBO
Eileen's Escape: 021-C Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
This home is professionally managed by Pretty Picky Properties Luxurious Chatham Home, Heated Saltwater Pool, Newly Ren ...
From $1124 per night (USD)
VRBO
From $1016 per night (USD)
Expedia
Barefoot Bungalow: 330-C Exquisite Chatham Home, Easy Access to Town, Bike Trail
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Exquisite Chatham Home, Easy Access to Town, Bike Tr ...
From $1016 per night (USD)
Expedia
From $948 per night (USD)
VRBO
Luxurious Home with Pool & Game Room in Cape Cod
Bedrooms:
4
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 $948 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Townhouse-style condo at The Hammond House located across from Lighthouse Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of The Hammond House, a townhouse-style condo in the Lighthouse Beach area, ideally situated across f ...
From $270 per night (USD)
Expedia
From $835 per night (USD)
VRBO
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 $835 per night (USD)
VRBO
From $1559 per night (USD)
Expedia
Great Cockle Cove Home!
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Family Retreat Destination! Let this 7 bedroom offering 2 queens, 4 twin, 2 full beds and 2 sets of bunk beds, spread o ...
From $1559 per night (USD)
Expedia
From $691 per night (USD)
VRBO
LOCATION & VIEW - Water Front Home In Chatham Village
Bedrooms:
0
Bathrooms:
3
Sleeps:
6
Fully renovated cottage on little mill pond. Renovation completed may 2016. A 4 minute walk to town of chatham. 3 bedroo ...
From $691 per night (USD)
VRBO
From $1019 per night (USD)
Expedia
The Barn at Hardings Beach
Bedrooms:
4
Bathrooms:
7
Sleeps:
16
Experience the ultimate getaway at this stunning 7-bedroom retreat, just a mile from Cape Cod’s pristine beaches. Enjoy ...
From $1019 per night (USD)
Expedia
From $1826 per night (USD)
VRBO
The Gables: 364-C Chatham Resort Style Estate with Heated Pool, Close to Everything
Bedrooms:
9
Bathrooms:
8
Sleeps:
16
This property is professionally managed by Pretty Picky Properties Chatham Resort Style Estate with Heated Pool, Close ...
From $1826 per night (USD)
VRBO
Click For Pricing
Expedia
Sunny, Cape-style home with a game room, yard, firepit, & washer/dryer
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Chatham Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For Pricing
Expedia
From $531 per night (USD)
VRBO
Direct Private Beach Access (2290)
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover the perfect blend of luxury and convenience in this beautiful 2-bedroom, 2-bath waterfront townhouse that offer ...
From $531 per night (USD)
VRBO
$Awesome Location! Right on the Chatham \Loop\, Perfect for Long Walks!$
From $756 per night (USD)
Expedia
Awesome Location! Right on the Chatham \"Loop\", Perfect for Long Walks!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Awesome Location! Right on the Chatham "Loop", it is Perfect for Long Walks! This 4-bedroom Cape House is close to town ...
From $756 per night (USD)
Expedia
Click For Pricing
VRBO
Prime Chatham Retreat with Pool, Spa & Style RPAM093
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Welcome to your luxurious vacation rental in the exclusive enclave of Chatham, MA! This stunning homes boasts three spac ...
Click For Pricing
VRBO
From $1573 per night (USD)
VRBO
House In The Heart Of Chatham Village
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The perfect location: in the heart of Chatham Village with outstanding views of Mill Pond, one of Chatham's most scenic ...
From $1573 per night (USD)
VRBO
From $881 per night (USD)
VRBO
Newly Remodeled Seaside Getaway with Forest Beach in your backyard!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Newly renovated home with ocean views and Forest Beach right in your backyard. Swim, lounge, kayak, hike, or play tennis ...
From $881 per night (USD)
VRBO
From $231 per night (USD)
VRBO
Convenient to all amenities and beaches in Chatham
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
Studio cottage with queen bed, full bath and kitchenette. Backyard area with brick patio/pergola and grill with an outd ...
From $231 per night (USD)
VRBO
From $601 per night (USD)
VRBO
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 $601 per night (USD)
VRBO
From $321 per night (USD)
Expedia
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 $321 per night (USD)
Expedia
Click For Pricing
VRBO
Spacious Cape - Large Private Backyard, 3 Decks!
Bedrooms:
2
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 $539 per night (USD)
Expedia
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 $539 per night (USD)
Expedia
From $379 per night (USD)
VRBO
The Whistling Whale - Fantastic Location!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
We're delighted to introduce "The Whistling Whale," a charming upstairs apartment offering a fantastic rental experience ...
From $379 per night (USD)
VRBO
From $522 per night (USD)
Expedia
Charming 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 $522 per night (USD)
Expedia
From $1026 per night (USD)
VRBO
Beach Cottage 4BD/2BATH (2,138 sqft)
Bedrooms:
2
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 $1026 per night (USD)
VRBO
From $1001 per night (USD)
Expedia
Dog Friendly! Half mile to Hardings Beach, newly updated, modern coastal chic, great outdoor space
Bedrooms:
3
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 $1001 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Chatham Beach Cottage + loft Walk to the Beach
Bedrooms:
1
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 $404 per night (USD)
VRBO
From $1238 per night (USD)
Expedia
Charming and updated home with private gardens and patio!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Discover a charming and updated vacation rental that comfortably sleeps eight, ideally situated on "The Loop." This home ...
From $1238 per night (USD)
Expedia
From $548 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 $548 per night (USD)
VRBO
From $778 per night (USD)
Expedia
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 $778 per night (USD)
Expedia
From $984 per night (USD)
VRBO
Charming two year old 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 $984 per night (USD)
VRBO
From $488 per night (USD)
Expedia
Bright S. Harwich Home, Private Backyard, Close to Beaches, Bike Trail & Shops
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Beautiful single family home in South Harwich, conveniently located right off of Rt. 28. Only 500 feet from the Cape Cod ...
From $488 per night (USD)
Expedia
From $971 per night (USD)
VRBO
Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham! Experience beautiful water views with y ...
From $971 per night (USD)
VRBO
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Expedia
🐶 Dog Friendly Fenced in Yard! 3/2 🏠 1.1 mi to 🏝 WIFI - perfect fall rental!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Modern 3 bedroom, 2 full bath ranch style home located in Chatham! 1/10th of a mile to Old Colony Bike path and 1.1 mile ...
Click For Pricing
Expedia
From $407 per night (USD)
VRBO
Chatham Seascape
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This home is represented by Nauset Rental, a local vacation rental management company. The perfect vacation destinatio ...
From $407 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful 3 bedroom Cape with spacious deck and hot tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Lovely modern 3 bedroom home, located on a quiet cul-de-sac is the perfect place for a family vacation. Hop on the bike ...
Click For Pricing
Expedia
From $331 per night (USD)
VRBO
Updated Beach House Deck Outdoor Shower!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: 16670 - A Touch of Blue: Updated Beach House Deck Outdoor Shower! The Space: Nautical colors and floods of nat ...
From $331 per night (USD)
VRBO
From $595 per night (USD)
Expedia
Enjoy Classic Chatham Charm and Easy Stroll to Downtown!
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
<p>Located in Chatham, this welcoming vacation home brings it all within your reach. There's convenient onsite parking, ...
From $595 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Marta (my wife) and I are two Canadians who now call Massachusetts our home. Our lovely place in South Chatham is our ne ...
From $412 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Riviera Sunset Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $368 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Jean's Dream - Newly Renovated Cape House .9Miles from the Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Escape to Jean's Dream a charming Cape house in South Chatham, MA. This delightful newly renovated rental features 2 bed ...
From $515 per night (USD)
VRBO
From $418 per night (USD)
VRBO
Cockle Cottage - Renovated Chatham Cape House .9 Miles from Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Indulge in a memorable stay at Cockle Cottage in Chatham, MA. This inviting rental boasts 2 bedrooms, 1 bathroom and com ...
From $418 per night (USD)
VRBO
Click For Pricing
VRBO
Brand New Home & 5 Minute Walk to Ridgevale Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our brand new 4-bedroom house in Chatham! Our 2250 square foot home sleeps up to 8 guests and is perfect for ...
Click For Pricing
VRBO
From $620 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 $620 per night (USD)
Expedia
From $418 per night (USD)
VRBO
Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling
Bedrooms:
2
Bathrooms:
2
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 $418 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $762 per night (USD)
VRBO
Enjoy a relaxing retreat. Easy access: Beaches, Bike Path, & Great restaurants.
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
This charming, tastefully decorated, and bright home includes a cheerful yellow fully equipped kitchen with a unique isl ...
From $762 per night (USD)
VRBO
From $890 per night (USD)
Expedia
Located in quiet Riverbay directly on the river; kayak to Jackknife 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 $890 per night (USD)
Expedia
From $668 per night (USD)
VRBO
Views of Eastward Ho Golf Course from the backyard!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This North Chatham property offers views of Eastward Ho Golf Course from the backyard. The antique Cape-style home accom ...
From $668 per night (USD)
VRBO
Click For Pricing
Expedia
Spacious Waterfront Home on Ryder's Cove! Pet Friendly too!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Contemporary 4 bedroom home located on Ryder's Cove in North Chatham. Plenty of space to spread out, with different liv ...
Click For Pricing
Expedia
From $757 per night (USD)
VRBO
Pristine Chatham home walkable to town, CBI, Fish Pier and baseball field
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Chatham retreat CLOSE to EVERYTHING, walk to CBI, fish pier, town, baseball field etc. Completely remodeled to perfectio ...
From $757 per night (USD)
VRBO
From $663 per night (USD)
Expedia
Walk to The Monomoy Wildlife Sanctuary. Great space for relaxing and entertaining
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Plan your next vacation by the beach in this charming 3 bedroom, 2 bath home, which comfortably sleeps six with a double ...
From $663 per night (USD)
Expedia
Click For Pricing
VRBO
Located in a quiet neighborhood, less than a mile from downtown Chatham
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This home is ideal for your family vacation! Located in a quiet neighborhood, it's less than a mile from downtown Chatha ...
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VRBO
From $540 per night (USD)
Expedia
Classic, airy Chatham cottage minutes from beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
**House is cleaned, disinfected & aired out between guests** Welcome to Cranberry Cottage, a cozy 2 BR, 1 BA cottage ce ...
From $540 per night (USD)
Expedia
From $558 per night (USD)
VRBO
5 Bedroom Chatham Retreat on Quiet Street
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Spacious 5 bedroom home in a great location in Chatham! This home can comfortably accommodate your entire family. Beauti ...
From $558 per night (USD)
VRBO
Click For Pricing
Expedia
Historic Cottage on White Pond, near Downtown Chatham and beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Affectionately named the "Chit-Chat", this classic 1920's 2 bedroom Cape Cod cottage is near downtown and Chatham's best ...
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Expedia
From $880 per night (USD)
VRBO
Red Door Retreat in Chatham
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Come make wonderful memories at this beautiful 3 bed/2.5 bath home. 4 min drive to beach & town. Cathedral ceiling livin ...
From $880 per night (USD)
VRBO
From $764 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 $764 per night (USD)
Expedia
From $605 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 $605 per night (USD)
VRBO
From $661 per night (USD)
Expedia
Summerwind - Ocean views and walk to beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Beautiful well maintained home with fabulous views of Nantucket Sound and a short walk from driveway to beach. ...
From $661 per night (USD)
Expedia
From $2467 per night (USD)
VRBO
Chatham Gem with Pool & High-End Style RPAM104
Bedrooms:
3
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 $2467 per night (USD)
VRBO
From $595 per night (USD)
Expedia
18 Bearberry Lane South Chatham - Rhododendron Cottage
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 $595 per night (USD)
Expedia
From $789 per night (USD)
VRBO
Private Beach, Beautiful Location, Well-Behaved Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This is a 5* "Exceptional" property but all its past reviews did not convey when it was recently relisted. Highwood Co ...
From $789 per night (USD)
VRBO
From $3161 per night (USD)
Expedia
New for 2025! Lovely home with heated pool, dock and the best views! RPMS158
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Michelle Sylvia coastal collection. Nestled on its own exclusive point within the private Stage Island enclave, this ...
From $3161 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Charming 2 bedroom condo on Private Beach by Outer Most Marina
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Get ready to relax in this 2-bedroom townhome in Chatham. This awesome property features 2 queen beds and 1 twin bed, pe ...
From $263 per night (USD)
VRBO
From $820 per night (USD)
Expedia
Beautiful house that is a walk to downtown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This quiet, charming home is in a highly sought-after location. You can leave your car parked and walk to breakfast, Oys ...
From $820 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Waterfront home with lovely lake views, great deck, sun porch & fireplace
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Mill Pond Vista Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $570 per night (USD)
VRBO
From $574 per night (USD)
Expedia
Over The Horizon: 048-CH Updated Chatham home with access to private beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Updated Chatham home with access to private beach S ...
From $574 per night (USD)
Expedia
From $854 per night (USD)
VRBO
Pool Coming June 2026, Game Barn, Bonus Cottage!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: 16683 - Cherry Blossom: Pool Coming June 2026, Game Barn, Bonus Cottage! The Space: A brand new pool will be i ...
From $854 per night (USD)
VRBO
From $472 per night (USD)
Expedia
Sandy Feet Retreat: 040-C Updated home on large lot near Hardings Beach in S. Chatham
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties. Secluded Home on 1.25 Acres Close to Hardings Beach ...
From $472 per night (USD)
Expedia
From $361 per night (USD)
VRBO
Pleasant Getaway halfway between beautiful Harwichport and Downtown Chatham
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
The perfect spot for a relaxing vacation! This lovely 3+ bedroom (1 King, 3 twins, and a twin/trundle) cottage in South ...
From $361 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Chatham Home w/ Spacious Deck: 2 Mi to Beaches!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience beachside bliss in Cape Cod when you stay at this 4-bedroom, 3-bath South Chatham vacation rental! This home ...
From $347 per night (USD)
Expedia
From $413 per night (USD)
VRBO
Walk to Pleasant St Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Comfortable and Charming Cottage, on a beautifully landscaped, private lot and walkable to one of Chatham's beautiful be ...
From $413 per night (USD)
VRBO
From $474 per night (USD)
Expedia
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 ...
From $474 per night (USD)
Expedia
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VRBO
Hot Tub! Steps to Oyster Pond Beach and Downtown Chatham.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover this beautifully landscaped, contemporary three-bedroom home, ideally situated on a quiet cul-de-sac, just a sh ...
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VRBO
From $1189 per night (USD)
Expedia
Upscale Elegance, Steps from Ridgevale Beach!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Enjoy your coffee overlooking Ridgevale Beach! Enjoy spectacular and expansive water views in this beautifully appointed ...
From $1189 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Chatham Cape Cod Near Bike Trail, 1 Mile to Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to a classic coastal getaway at this charming Chatham vacation rental. Located 1 mile from the shore and steps f ...
From $385 per night (USD)
VRBO
From $708 per night (USD)
Expedia
Roof Deck, Walk to Forest Beach, Fire Pit!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: 16679 - Inn Bloom: Roof Deck, Walk to Forest Beach, Fire Pit! The Space: Inn Bloom is perched on a small hills ...
From $708 per night (USD)
Expedia
From $1122 per night (USD)
VRBO
Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friend
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: 16680 - Seaside Sapphire: Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friendly! ...
From $1122 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Quintessential Cape directly on the Cape Cod Rail, Dog Friendly!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16682 - Nob Hill: Quintessential Cape directly on the Cape Cod Rail, Dog Friendly! The Space: In this Quintess ...
From $430 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Movie Theater Room, Direct Access to Bike Trail!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: 16681 - Summer On: Movie Theater Room, Direct Access to Bike Trail! The Space: Escape to this charming Chatham ...
From $349 per night (USD)
VRBO
Click For Pricing
Expedia
Charming ranch on quiet road.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This sunny, cozy Cape-style ranch is a short driving distance to both Harding's and Oyster Pond beaches and the quaint v ...
Click For Pricing
Expedia
From $519 per night (USD)
VRBO
Short walk to beach, A/C, pets okay, large yard
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedrooms - 1 Bathroom - Sleeps 4 A 3-night midweek stay - Monday to Wednesday - is offered at this home during the pea ...
From $519 per night (USD)
VRBO
From $2461 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 (4 kings) and 3.5 bath home with private pool. C ...
From $2461 per night (USD)
Expedia
From $881 per night (USD)
VRBO
Chatham Compound + Carriage House - Huge yard, Game Room, Kayaks, Sleeps 10
Bedrooms:
4
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
From $1498 per night (USD)
Expedia
NEW Water View! Exceptional Location! Walk to Town, Oyster Pond Beach, Bike Path
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Spectacular Coastal Property! Completely Reconstructed & Remodeled in 2023! Views of Oyster Pond & Short Walk to Oyster ...
From $1498 per night (USD)
Expedia
From $615 per night (USD)
VRBO
Walk to Main St and Oyster Pond in Chatham!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 16685 - Chatham Breeze : Walk to Main St and Oyster Pond in Chatham! The Space: Discover the epitome of Cape C ...
From $615 per night (USD)
VRBO
From $1586 per night (USD)
Expedia
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 exc ...
From $1586 per night (USD)
Expedia
Click For Pricing
VRBO
Secluded North Chatham Cottage for Entire Summer [July/August]!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Rare opportunity to spend the entire summer in North Chatham! This approximately 2,400 SF private residence is not typ ...
Click For Pricing
VRBO
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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

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Results: 667 Rentals