We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals with Pools in Chatham

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    R 12 354 Average
    |||
    |||
    R 0R 13 000+
    Suitability
    More filters
    Travellers to Chatham are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    19 Matching Rentals in ChathamView all 470 rentals
    Sort by:
    Default
    Spectacular Waterfront Townhome - Oyster Pond #321 / 14
    (6)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    14 Hallett Lane Chatham Cape Cod - Sand Simeon1 / 48
    (6)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    2 Captains Row E Chatham Cape Cod - Captain's Row1 / 26
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    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...
    See all reviews
    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...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    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...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    View all property information
    Location Information
    02650, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    8 Bedrooms, 11 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    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...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 8 Bedrooms, 11 Bathrooms, Sleeps 16
    Make Enquiry
    Spectacular Waterfront Home - Oyster Pond 31&321 / 28
    (2)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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 17 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...
    See all reviews
    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...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    4 Bedrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $5,150 per week Off-Season: $4,375 per week Click for More Photos, Map, and Availability Calendar The perfect place for a most memorable and rewarding vacation. New owners of this original Morris Island home have brought in all new furnishings...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, Sleeps 10
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Grill
    • 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...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Save time - get the best Chatham rentals sent straight to your email!
    Get the List
    Spectacular Waterfront Townhome - Oyster Pond #251 / 12
    (8)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    1 Bedroom, 6 Bathrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Hot Tub
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning New Construction with Pool in North Chatham! This beautiful home leaves nothing to want for. Built in 2017, the main house features 6000 square feet of fantastic living space including an in home cinema, game room, sleeping space for 18 and en suite bathrooms for each bedroom. The...
    View all property information
    Location Information
    02650, North Chatham, Chatham
    Holiday Rental House - 1 Bedroom, 6 Bathrooms, Sleeps 18
    Make Enquiry
    6 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    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...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 11
    Make Enquiry
    5 Bedrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $9350 per week Call about Off-Season Click for More Photos, Map, and Availability Calendar The entire family will enjoy this gorgeous, newly built 4+ BR home with a private association path down to Ridgevale Beach! The beach is close, there is a...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 5 Bedrooms, Sleeps 11
    Make Enquiry
    Spectacular Waterfront Townhome - Oyster Pond #311 / 13
    (9)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Internet Access
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rate: In-Season weeks of June 23 - August 24: $7,050 per week, including Cleaning and Linens! 11/01/2016-4/27-2018: $3,250/week 04/28-5/25: $3,950 05/26-6/22: $4,750 8/25-9/7: $5,150/week 9/8-10/31: $4350/week ALL RATES INCLUDE CLEANING AND LINENS Gorgeous town-house located on Oyster...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 2 Bedrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates: In-Season weeks of June 23 - August 24: $6,150 per week, including Cleaning and Linens! 11/01/2017-4/29/2018: $2,850/week 4/28-5/25: $3,350/week 5/26-6/22: $4,050/week 8/25-9/7: $4,450/week 9/8-10/31: $3650/week ALL RATES INCLUDE CLEANING AND LINENS! Gorgeous, new townhouse...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Condo/Apartment - 2 Bedrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates:6/23-8/24: $10,200/week 11/1/16-4/27 :$5650/week 4/29-5/27:$6500/week 5/26-6/22: $7900 per week 8/25-9/7:$7900/week 9/8-10/31: $6900/week ALL PRICES INCLUDE CLEANING AND LINENS! Weekly rentals from mid-JUNE to mid-SEPT Amazing town-home located steps from Oyster Pond with...
    View all property information
    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, Sleeps 10
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • 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...
    View all property information
    Location Information
    02659, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
    Make Enquiry
    List your property
    Owner log in