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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.
    11 Matching Rentals in ChathamView all 388 rentals
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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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    1 Bedroom, 6 Bathrooms, Sleeps 18 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    5 Bedrooms, Sleeps 11 Quick View
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    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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 11
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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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    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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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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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 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 17 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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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 10 Quick View
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    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: $5,750 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    2 Bedrooms, Sleeps 8 Quick View
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    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...
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    Chatham, Cape Cod 02633
    Condo/Apartment - 2 Bedrooms, Sleeps 8
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    2 Bedrooms, Sleeps 8 Quick View
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    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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, Sleeps 8
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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 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
    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10 Quick View
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    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...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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