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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.
    14 Matching Rentals in ChathamView all 394 rentals
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    Spectacular Waterfront Home - Oyster Pond 31&321 / 28
    (2)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Spectacular Waterfront Townhome - Oyster Pond #321 / 14
    (6)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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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    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
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    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 water 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 from...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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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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    Amenities & Details
    • Washer
    • Air Conditioning
    • Secure Parking
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 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
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    103 Bellamy Lane1 / 30
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    02650, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Amenities & Details
    • Grill
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2014
    We loved to stay in this luxurious and wonderful house! Anything is very clean and you don´t miss anything. Thank you for the nice "start bags", that is more than one...
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    About this property
    Welcome to Captain's Row! Enjoy easy resort style living in this newer Cape Cod Vacation Rental home in Chatham.   This home is in its own residential sub division and is close to beaches, restaurants, downtown and includes a community pool & tennis court (Only 130 steps from your door!). Also...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience 'Chatham Coastal Charm'. Popular Contemporary Cape Cod Vacation Rental home in Chatham with heated salt water gunite pool that is just a short walk to Hardings Beach (.3). Sleeps 10! Don't miss this 'fan favorite' Cape Cod Vacation Rental home in Chatham with heated pool that is very...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    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. Peak Summer Weekly Rates: $12,150- $13,500  Rents Saturday to Saturday in peak season Linens Included NEW Listing for 2018! Just off the historic Chatham “Loop,” this spacious (4,300+ sq. ft.), newly renovated, upscale...
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    6 Bedrooms, 5 Bathrooms, Sleeps 11 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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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 11
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    Spectacular Waterfront Townhome - Oyster Pond #311 / 13
    (9)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 2 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
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    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
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    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, with accommodations for up to 11, this lovely home is within close...
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    Location Information
    02659, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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