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Holiday Rentals with Pools in Chatham

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    20 Matching Rentals in ChathamView all 491 rentals
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    14 Hallett Lane Chatham Cape Cod - Sand Simeon1 / 48
    (6)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    2 Captains Row E Chatham Cape Cod - Captain's Row1 / 26
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Lorna Dune! Pet Friendly! A 5,000 square foot luxury 5 bedroom (sleeps 12 with extra bonus room), 5.5 bath vacation rental home in beautiful North Chatham. Walk to beach, Central air, free WiFi, and a heated swimming pool. Coastal comfort & style abound in this spacious home. First...
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    02650, Chatham, Cape Cod
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly situated Chatham rental features everything one is looking for in a Cape Cod rental. In the back yard, a stunning heated pool with attached spa awaits. Located close to Shore Road, you and your guests will enjoy the best of being near the ocean and close to Main Street. Stroll to...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    8 Bedrooms, 11 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Hot Tub
    • Waterfront
    • Grill
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rising majestically over Eldridge Point, overlooking Oyster River, Harding’s Beach, and Nantucket Sound, this extraordinary estate features the largest private shoreline in Chatham. Watch glorious sunsets while swimming in your infinity edge pool; or cook dinner in the outdoor kitchen while...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 8 Bedrooms, 11 Bathrooms, Sleeps 16
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on its own point within exclusive and private Stage Island, this Chatham home offers both an idyllic setting and modern comforts. Enjoy stunning views over Stage Harbor throughout the home and direct water access from the private dock (boats under 20' can be brought and tied up for your...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Robert Paul Properties Luxury collection rental home. Imagine walking through the front door to a stunning view of the Harbor overlooking Chatham Pier and your own heated pool. Relax in the hot tub or sit on the back patio and take it all in. This waterfront vacation home has magnificent views...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
    Spectacular Waterfront Townhome - Oyster Pond #321 / 14
    (6)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Wi-Fi
    • Balcony
    • Porch
    • Air Conditioning
    • Patio
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    You got six -stars on my rating, the house was just perfect, location wise couldn't be any better,close to downtown and great views, we couldn't ask for anything more, we...
    Reviewed 21 February 2017
    Great property & perfectly located. Close to beaches, shopping & restaurants. The house is very beautiful and spacious. Quick check in and check out & quiet &amp...
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    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Incredible two bedroom, three full bathroom end-unit with gorgeous direct water views of Oyster Pond. Beautifully decorated with charming interior decor....
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    103 Bellamy Lane1 / 30
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2018
    5 stars. We had a great family vacation in this house. The pool area is fantastic. The house is clean and comfortable. It was large enough for 10 of us. The kitchen is very well...
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    About this property
    Tucked in the private Cannon Hill setting, this enchanting 4 bedroom, 3 full and 1 half bathroom home with a large 40 x 20 heated salt-water pool offers tons of comfort and is perfect for your summer getaway. Just a short 3 minute stroll away, on the calm waters of Pleasant Bay, a private...
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    Location Information
    02650, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Spectacular Waterfront Townhome - Oyster Pond #251 / 12
    (8)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Air Conditioning
    • Secure Parking
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    Oyster Pond is an amazing spot. Our family had the opportunity to enjoy the 4th of July in Chatham and we selected unit 25 at Oyster Pond! It was the perfect spot for a family...
    Reviewed 16 August 2017
    At the top of our list for vacation rentals in Cape Cod. Our extended family of 8 rents every year in Chatham and this rental is at top of our list. Luxury accommodations - 4...
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    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. This is a stunning four bedroom, four and a half bath spacious end-unit townhouse with spectacular views of Oyster Pond. Unit 25 is the largest...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    Spectacular Waterfront Home - Oyster Pond 31&321 / 28
    (2)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Children's Pool
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 2014
    The house was incredible. I have rented homes across the world with our family, and we are extremely picky in terms of 1. Cleanliness 2. renovation/newness 3. Location 4...
    Reviewed 18 July 2014
    The units we rented at Oyster Pond exceeded our expectations. These two units (31 & 32) were very well appointed with TVs in every room, modern appliances, comfortable...
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    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Incredible four bedroom, five and a half bathroom double end townhouse with gorgeous direct water views of Oyster Pond. Townhomes 31 and 32 are rented...
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Waterfront
    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious Custom Chatham Home Plus Guest Cottage with water views NEW for 2019 -- Heated salt-water pool, outdoor kitchen and spa! Linens included, fully updated during 2018 season Rents Saturday to Saturday in peak season This immaculate custom home features 3 master en suite bedrooms and is set...
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Chatham Resort Feel: Sleeps 16, Heated Pool/Spa, Renovated, Roomy, Upscale. Rents Saturday to Saturday in peak season Linens Included Please click on the 'Virtual Tour'tab to take a 3D tour of the home Just off the historic Chatham “Loop,” this spacious (4,300+ sq. ft.), newly renovated,...
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Patio
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located next to the world famous Monomoy National Wildlife Refuge on Morris Island, this 4 bedroom, 3 bath home features all the amenities needed for a spectacular Chatham vacation. Spend time sunning and swimming at the Quitnesset Association private beach down the road. Come home and relax by...
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Updated Chatham Family Compound Sleeps 14, Large Heated Pool with Spa, Walk to Town Rents Saturday to Saturday in Peak Season Linens Included If you relish the charm of Chatham but love modern amenities, here's the resort style vacation destination for your larger group. The acre-plus property...
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a property which is located in one of the most desirable towns on Cape Cod and features amenities that you usually have to drive to and pay extra for? Well look no further... welcome to 324 Deer Meadow Lane in Chatham. Featuring five bedrooms, three full and one half baths, a heated...
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Spectacular Waterfront Townhome - Oyster Pond #311 / 13
    (8)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Grill
    • Outdoor Dining Area
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2017
    Our week at Oyster Pond was absolutely magical. the townhome was so beautiful and comfortable and we couldn't have imagined a more perfect home for our week in Chatham. The...
    Reviewed 31 July 2017
    We've stayed in many places over the years in Chatham and this townhouse was the nicest by far! Waterfront, pool, tennis, immaculately clean, sheets/towels provided, modern...
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    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Beautiful two bedroom plus a den and a loft, two and a half bathroom townhome with gorgeous direct water views of Oyster Pond. Beautifully decorated with...
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This recently renovated 5BR/3.5BA two-story farmhouse sits on almost one acre of land and is close to multiple beach locations. Enjoy an expansive backyard deck or lounge by the private heated pool. Take the bike path, located directly in front of the property, or drive 1.2 miles to Hangar B....
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're searching for the perfect home base for your next Cape Cod getaway, look no further than this spacious 4-bedroom, 3-bathroom Chatham vacation rental house! Boasting 2,600 square feet of tastefully appointed living space, a seasonal pool, and accommodations for up to 11, this lovely home...
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    Location Information
    02659, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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