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Holiday Rentals with Pools in Chatham

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32 rentals in Chatham.
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Location! Pool and Spa! 2 Primary Suites, Walk to Town, CBI, Beach
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Chatham Family Estate. Heated Pool. Sleeps 16+, AC, walk to town and beach.
Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps, All pools
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Living and Dining Room
1st Floor Master Bedroom
2nd Floor Master Bath
Spectacular Waterfront Townhome - Oyster Pond #25
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Dining Room
Kitchen Nook View
Master Bedroom
Spectacular Waterfront Townhome - Oyster Pond #31
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Spectacular Waterfront Townhome - Oyster Pond #32
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Family friendly luxury home with heated pool and spa
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Perfect House to Enjoy Family & Friends!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Updated Chatham Family Compound, Heated Pool & hot tub, 489-C
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps, All pools
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New Waterfront Townhome
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Pool and Private Association Beach In Cannon Hill
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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New Waterfront Townhome
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Newly Remodeled, One Mile to Chatham Village, 4 Minute Drive to Beach: 032-C
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Chatham Coastal Charm -Heated pool & walk to beach - 93 Bucks Creek Rd Chatham
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Families: Enjoy Harwich, Pool & Large Hot Tub
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps, All pools
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Chatham Landmark Estate, Large Guest House, Pool 177-C
Holiday Rental House
8 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps, All pools
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Spectacular Waterfront Home - Oyster Pond 31&32
Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps, All pools
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SPECTACULAR WATERFRONT RETREAT WITH HEATED POOL!!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Alluring Chatham in-town home with pool, walk to it all: 052-CS
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Newer Chatham Townhome with Community Pool and Tennis: 2 Captains Row E Chatham
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Heated pool and breathtaking views!
Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beachfront Cape w/ Dock Hot Tub Fire Pit Outdoor Kitchen Boats Kayaks - Pets Ok!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Ryder's Cove Resort: Heated Pool, Private Dock: 676-C
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Superb, Upscale with Pool and Hot Tub in Chatham: 002-C
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Renovated Luxury Chatham Home with Pool & Hot Tub: 935-C
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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New Luxury Home in Chatham with Pool & Hot Tub, Walk to Town: 279-C
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Private pool, farmer's porch, fire pit and deck for panoramic views.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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POOL/HOT TUB, walking distance to Chatham Village & CBI!
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps, All pools
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AC, Pool, Hot Tub, Fenced Yard, Beach vacation home
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Charming Chatham condo - Oyster Pond views, pool, tennis court and water access
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Stunning Chatham Luxury Property With Pool, Spa and Beach Access
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps, All pools
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Chatham new construction | Heated Pool | See completed photos!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Beach Chic Chatham 5⭐ Private-Newly Renov'd-Hear Waves at Night-5m Walk to Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Water View-Walk town/beach, pets considered, Linen Option
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
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Convenient to all amenities and beaches in Chatham
Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Newly Renovated- Large Deck, Fire Pit, Game Room & Many Amenities
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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LOCATION! LOCATION! LOCATION! Water Views! Walk to beach and walk to town!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beach Chic Chatham 5 ⭐ Family Retreat-5 min walk to Private Beach-Newly Renov'd
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
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Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Sanitized! Pool Table, Bar, Ping Pong, Sun Rm, Deck,4 BR, Private
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
More info
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Near Harding's Beach, 4 min walk to Oyster River...AC added 2021
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN - Close to Beaches, and Downtown
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Fully Updated Chatham Cottage Near Hardings Beach
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Chatham Village Center 3br - In Town & Near Beach/Chatham Bars Inn
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Exceptional Chatham Cottage
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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