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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 ...
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VRBO
From $1151 per night (USD)
Expedia
WATERFRONT home close to Downtown Chatham!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Soak up the sun while enjoying the lush outdoor space at our waterfront home, Queen’s Quarters. Bring or rent a kayak or ...
From $1151 per night (USD)
Expedia
From $590 per night (USD)
VRBO
0.6 Miles to Beach Great for families!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: 16677 - Nautical Nest: 0.6 Miles to Beach Great for families! The Space: Seals swim off shore while you soak u ...
From $590 per night (USD)
VRBO
From $720 per night (USD)
Expedia
Game Room, Rooftop Deck, Fire Pit!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: 16678 - Jawsome Getaway: Game Room Rooftop Deck Fire Pit!! The Space: Chatham is the hub of entertainment and ...
From $720 per night (USD)
Expedia
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VRBO
Bright & Spacious Ridgevale Beach Getaway!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Close to Ridgevale Beach! This spacious 4 bedroom, 3 bath vacation home is well maintained and just under a mile to popu ...
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VRBO
From $773 per night (USD)
VRBO
Beautiful Chatham home...3 minute walk to salt water ocean beach!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Great location, spacious home and yard, private deck with brand new gas grill and comfy furniture. Beautifully decorated ...
From $773 per night (USD)
VRBO
From $304 per night (USD)
VRBO
Chatham Getaway- Completely Renovated Cape Cottage w/ Linens Included
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
*Contact us for information on long-term booking opportunities!* This home is represented by Nauset Rental, a local vac ...
From $304 per night (USD)
VRBO
From $218 per night (USD)
Expedia
Charming Chatham Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Prepare to be charmed by this quintessential Cape Cod beach cottage, tucked into a quiet residential neighborhood equidi ...
From $218 per night (USD)
Expedia
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
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Expedia
Charming and cozy, and right off the Chatham Loop!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the charm and coziness of Cedar Street, a highly desirable location just off the Chatham Loop! This vacation re ...
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Expedia
From $844 per night (USD)
VRBO
Beautiful and Pristine Rental in South Chatham.. Recently Reduced!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
REDUCED FOR REMAINING SUMMER WEEKS!!! INQUIRE WITHIN! Awesome Three Bedroom Home on a Quiet Cul-de-sac in South Chat ...
From $844 per night (USD)
VRBO
From $880 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 $880 per night (USD)
VRBO
From $431 per night (USD)
VRBO
Great Cape Cod Getaway!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Guests are sure to enjoy a memorable vacation or special occasion in this fully furnished, 3 bedroom/2.5 bath cape home ...
From $431 per night (USD)
VRBO
From $785 per night (USD)
Expedia
Stroll Chatham's Historic Downtown / Shops, Dining, Galleries, Etc.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful home located in the heart of Chatham! This lovely home offers all the amenities and decor of a modern house wh ...
From $785 per night (USD)
Expedia
From $923 per night (USD)
VRBO
THE CHATHAM TREEHOUSE 7 minutes from the Village
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to the Treehouse, just 7 mins from the village of Chatham! This beautiful, private property is nestled in the wo ...
From $923 per night (USD)
VRBO
From $538 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 $538 per night (USD)
Expedia
From $380 per night (USD)
VRBO
Newly Renovated Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Oh Buoy Oh Buoy Escape to Oh Buoy Oh Buoy, our tastefully renovated Chatham cottage just one mile from the soft, white ...
From $380 per night (USD)
VRBO
From $1019 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 $1019 per night (USD)
Expedia
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VRBO
Downtown Chatham 4 Bedroom House
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 bedroom house at end of private, dead-end street in Downtown Chatham. 2 decks, views of conservation land. Listen to ...
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VRBO
From $1124 per night (USD)
Expedia
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)
Expedia
From $311 per night (USD)
VRBO
Bright home walking distance to Main Street with great patio, firepit & bikes
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Queen Anne Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $311 per night (USD)
VRBO
From $319 per night (USD)
Expedia
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 $319 per night (USD)
Expedia
From $204 per night (USD)
VRBO
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 $204 per night (USD)
VRBO
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Expedia
Lovely 3 BR Home in Harbor Coves, North Chatham...Peaceful Setting!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This lovely cape with 3 bedrooms and 2 1/2 baths sits privately on over an acre of land. A classic, antique home filled ...
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Expedia
From $378 per night (USD)
VRBO
Beautiful Cape home. Minutes from beaches, restaurants, bike paths & shopping.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spacious and conveniently located. Close to supermarket, gas station, banks, post office, restaurants and more. Central ...
From $378 per night (USD)
VRBO
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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 ...
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Expedia
From $355 per night (USD)
VRBO
Walk to Beach: Chatham Getaway w/ Sunroom!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You’ll be able to hear the crashing waves from every corner of this Chatham, MA, vacation rental. This 3-bedroom, 2-bath ...
From $355 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $601 per night (USD)
VRBO
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 $601 per night (USD)
VRBO
From $567 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 $567 per night (USD)
Expedia
From $1245 per night (USD)
VRBO
Pool and large yard!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
North Chatham home with a large yard and a lovely pool. The large front room is perfect for reading or watching TV, pla ...
From $1245 per night (USD)
VRBO
From $2923 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 $2923 per night (USD)
Expedia
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
From $968 per night (USD)
Expedia
Newly Renovated Guest House For 10 Near The Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to our charming vacation house located in Harwich, Massachusetts! Our property is perfectly located near the bea ...
From $968 per night (USD)
Expedia
From $828 per night (USD)
VRBO
Enjoy a relaxing retreat. Easy access: Beaches, Bike Path, & Great restaurants.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This charming, tastefully decorated, and bright home includes a cheerful yellow fully equipped kitchen with a unique isl ...
From $828 per night (USD)
VRBO
From $1027 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 $1027 per night (USD)
Expedia
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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 ...
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VRBO
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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 ...
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Expedia
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Expedia
Chatham pond access with view
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy our large back yard and private road that leads to the Pond behind the house, for fishing, non-motor boating, padd ...
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Expedia
From $402 per night (USD)
Expedia
Cozy Chatham Cottage walk to Hardings beach Restaurants & downtown.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Newly remodeled 1950's era cottage with all the comforts for a great visit. Just off the living room and thru French do ...
From $402 per night (USD)
Expedia
From $422 per night (USD)
VRBO
Cape Escape - Family-Friendly Chatham Retreat
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 $422 per night (USD)
VRBO
From $423 per night (USD)
Expedia
Classic Cape House Walking Distance to the Beach - Many recent upgrades
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Recent upgrades: Complete interior painted (March 2025); Main dining table refinished (April 2025); Downstairs bathroom ...
From $423 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 $892 per night (USD)
VRBO
Beautifully renovated home, outdoor space, pet considered
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Sea~a~Bella - Your perfect Chatham family vacation is here. You will find three beautiful, scenic beaches within walking ...
From $892 per night (USD)
VRBO
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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 ...
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Expedia
From $483 per night (USD)
VRBO
Sarah-N-Dipity: Cozy Cottage Near Ridgevale Beach
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 $483 per night (USD)
VRBO
From $1056 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 $1056 per night (USD)
VRBO
From $384 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 $384 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Beautifully Renovated Cape on Bike Trail, 1 mile to Downtown Chatham and Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Charming Cape house recently renovated less than a mile to Downtown Chatham for shopping and restaurants. Located on a q ...
From $270 per night (USD)
VRBO
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VRBO
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 ...
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VRBO
From $429 per night (USD)
Expedia
Home near beach & tennis/basketball court with firepit, grill, & patio
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Sea Star Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $429 per night (USD)
Expedia
From $835 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 $835 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 $642 per night (USD)
VRBO
Stunning Waterfront Property Overlooking Pleasant Bay (2327)
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This beautiful rental home offers a serene and picturesque setting with marsh front views, water access just feet away, ...
From $642 per night (USD)
VRBO
From $617 per night (USD)
Expedia
Dogs welcome, huge yard right next to Rail Trail!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: 17745 - Happy Tails: Dogs welcome, huge yard right next to Rail Trail! The Space: Discover Coastal Elegance in ...
From $617 per night (USD)
Expedia
From $679 per night (USD)
VRBO
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 $679 per night (USD)
VRBO
From $1254 per night (USD)
Expedia
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 $1254 per night (USD)
Expedia
From $454 per night (USD)
VRBO
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 $454 per night (USD)
VRBO
From $475 per night (USD)
Expedia
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 $475 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Walk to Private Beach on Buck's Pond!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: 17721 - Float On: Walk to Private Beach on Buck's Pond! The Space: Welcome to your dream vacation home nestled ...
From $211 per night (USD)
VRBO
From $786 per night (USD)
Expedia
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 $786 per night (USD)
Expedia
From $356 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 $356 per night (USD)
VRBO
From $1064 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 $1064 per night (USD)
Expedia
From $644 per night (USD)
VRBO
Pool & Additional Bath Coming June 2026, Game Barn!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: 16683 - Cherry Blossom: Pool & Additional Bath Coming June 2026, Game Barn! The Space: A brand new pool will b ...
From $644 per night (USD)
VRBO
From $1247 per night (USD)
Expedia
Chatham Vacation Rental With Pool and Charm to Spare! RPAM096
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Located in one of Cape Cod’s premier resort towns, 764 Riverview Drive offers everything a discerning vacationer is look ...
From $1247 per night (USD)
Expedia
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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 ...
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VRBO
From $398 per night (USD)
VRBO
Chatham Getaway w/ Trail Access, 2 Mi to Beaches!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your next Cape Cod adventure awaits at this cozy Chatham vacation rental. Perfect for a memorable family getaway on the ...
From $398 per night (USD)
VRBO
From $1163 per night (USD)
VRBO
Lovely Chatham Cape House on 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 $1163 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Explore Downtown and Pleasant Bay!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: 18836 - Sunny Escape: Explore Downtown and Pleasant Bay! The Space: Your Brewster vacation awaits, in this id ...
From $515 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Affordable Family Getaway Sleeps 7, Near Bike Path, Beach, Golf, Harwich Center
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Cape-style home in a family-friendly neighborhood. Open floor plan with large living room and dining room (seating for 6 ...
From $407 per night (USD)
VRBO
From $2075 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 $2075 per night (USD)
VRBO
From $566 per night (USD)
VRBO
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 $566 per night (USD)
VRBO
From $563 per night (USD)
VRBO
3br, huge private yard, halfway between 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 $563 per night (USD)
VRBO
From $860 per night (USD)
VRBO
Fido friendly Walk to Red River Beach - Sleeps 20 - Hot tub - Bring your boat!
Bedrooms:
5
Bathrooms:
8
Sleeps:
20
Last minute cancellation 8/9-8/16/25. Book 3 or 7 nights $550 per night. Discount price deducted at inquiry. Come and r ...
From $860 per night (USD)
VRBO
From $1233 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 $1233 per night (USD)
Expedia
From $202 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 $202 per night (USD)
VRBO
From $413 per night (USD)
Expedia
3 bed, 2 bath, dog-friendly, central AC, Wifi sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom - 2 Bathrooms - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. M ...
From $413 per night (USD)
Expedia
From $372 per night (USD)
VRBO
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 $372 per night (USD)
VRBO
From $381 per night (USD)
Expedia
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 $381 per night (USD)
Expedia
Click For Pricing
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 $441 per night (USD)
VRBO
Charming Cape Cod home, central to everything! Pet-friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming Cape Cod home is central to all of the Cape. Our three bedroom, two bath home (+ outdoor shower!) is a gre ...
From $441 per night (USD)
VRBO
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VRBO
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 ...
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VRBO
From $938 per night (USD)
VRBO
Family & Dog friendly Chatham house with tennis &water access
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Welcome to Camp Moonpenny- a 3 house, 6 acre property in the Sears Point area of Chatham. While only 2 miles from Main S ...
From $938 per night (USD)
VRBO
From $971 per night (USD)
VRBO
Chatham dog-friendly family retreat with tennis, water views & access!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Linens/towels provided. Option to book 2 adjacent houses for parties of up to 18. Escape with your family and friends t ...
From $971 per night (USD)
VRBO
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Expedia
Wonderful dog friendly rental with access path to a private beach deeded at White's Pond!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Wonderful dog friendly rental for the whole family, with access path to a private beach deeded at White's Pond! Close to ...
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Expedia
From $1002 per night (USD)
VRBO
Private and pet friendly with expansive back deck
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Private and pet friendly. The bright, open living and dining area features a large slider that leads directly to the bac ...
From $1002 per night (USD)
VRBO
From $3635 per night (USD)
Expedia
Stroll to Chatham's Popular Shops & Dining / Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
Stroll to Chatham's Popular Shops & Dining / Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound . Recent ...
From $3635 per night (USD)
Expedia
From $478 per night (USD)
VRBO
Chatham EsCAPE: Pet Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This charming 3-bedroom, 2-bathroom home is ideally situated between the tranquil Ridgevale Beach and the vibrant Chatha ...
From $478 per night (USD)
VRBO
From $401 per night (USD)
Expedia
Close to Beach Renovated Dog Friendly Cape Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
4 minutes from the beach and nestled on a spacious half acre set back more than 250 feet on a private road, this newly r ...
From $401 per night (USD)
Expedia
From $2376 per night (USD)
VRBO
Exclusive Harwich Haven: Pool, Spa and More RPAM068
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to 8 Bascom Hollow, a truly luxurious Cape Cod escape. Located in East Harwich, this home offers tenants an exce ...
From $2376 per night (USD)
VRBO
From $734 per night (USD)
Expedia
Don't Think Twice: Spacious Beachside Retreat
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
4 Bedroom - 2.5 Baths - Sleeps 11 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $734 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Two-story dog-friendly retreat with enclosed yard, playset, W/D, & firepit
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Sand Dollar Dreams Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $367 per night (USD)
VRBO
From $270 per night (USD)
Expedia
New! Chatham Cottage- 1 Mile to Downtown & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to our charming 2 bed/1 bath North Chatham cottage! A short walk to Chatham's best beaches and downtown shops an ...
From $270 per night (USD)
Expedia
From $655 per night (USD)
VRBO
Sandy Spot: Walk to Beach, Sleeps 10
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
4 Bedroom - 2.5 Baths - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $655 per night (USD)
VRBO
Click For Pricing
Expedia
Steps to Chatham's Historic Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Luxury Retreat on Popular Main Street Chatham. This unique hide-a-way is a spacious 2 bedroom 2nd floor condo in the he ...
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Expedia
From $573 per night (USD)
VRBO
Steps to Chatham's Historic Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Luxury Retreat on Popular Main Street Chatham. This unique hide-a-way is a spacious 2 bedroom 2nd floor condo in the he ...
From $573 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful 5 BR property with pool and hot tub!
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
2024 Rental Rates: In-Season: $11,000 per week, Plus Fees and Taxes No Off-Season Click for More Photos, Map, and A ...
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Expedia
From $570 per night (USD)
VRBO
Stroll To Lighthouse Beach or Chatham's Charming Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
NEW LOWER PRICING! Fourth of July Week is Still AVAILABLE! Best spot in town for the Chatham Independence Day Para ...
From $570 per night (USD)
VRBO
From $666 per night (USD)
Expedia
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 $666 per night (USD)
Expedia

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