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Chatham Rentals for Seniors

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    Travelers to Chatham are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    30 Matching Rentals in ChathamView all 650 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Cape Cod Chatham Escape! Beach Chic Vacation Rental 5 min walk to beach Private1 / 47
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Cape Cod Escape 5 min Walk to Beach! Private-Newly Renovated-Hear Waves at Night1 / 48
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Chatham, 3 bedroom, 2 bath, walk to Ridgevale Beach and the warm waters of Nantucket Sound, south side of 28, whirlpool, stainless appliances, deck, gas grill, outdoor shower, all the amenities, fully stocked, washer and dryer. Everything you might need. Clean and comfortable, large yard, color...
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    Chatham, Cape Cod 02659
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    NOTE - Not available to book until mid Feb deadline for family and friends to sign up. Wonderful, family-friendly, 5- bedroom house close to town. One ground-floor bed/bath. Fenced-in, flower filled, back yard with outdoor shower, grille, table and chairs, deck/patio. Walking distance to town or...
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    Chatham, Cape Cod 02633
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    Quiet Lakeside Cottage - Ideal for Couple1 / 11
    (12)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 16, 2016
    I loved the cottage, the location, and all the amenities. Helen thought of everything I would need for a restful stay. The cottage is airy and clean. The space is used very...
    Reviewed July 20, 2016
    When we drove up to the cottage, our hearts sunk a bit at how close the neighboring cottages were. Once we got settled in, though, we found that the Lakeview Colony is very...
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    About this property
    At this quiet lakeside cottage you can experience classic Cape Cod with all the modern amenities -- wireless internet, cable TV, air conditioning. Enjoy beautiful sunsets as well as swimming and canoeing at the lake---and only be a short trip to the beach or Chatham center. The cottage features...
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    Chatham, Cape Cod 02633
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife! Welcome to The Chatham Bars Carriage House, located within walking distance to Historic Main St. with it's endless variety of boutiques, restaurants, galleries, and nightlife! Enjoy this traditional, yet well-appointed...
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    Chatham, Cape Cod 02633
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    A "Shore Thing" in Chatham!1 / 17
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Internet Access
    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cape Cod Dreaming by the Beach - Perfect for families to share! Relax by escaping to our newly refurbished and decorated classic Cape Cod cottage, just a short walk, 4/10 of a mile, to sandy Pleasant Street Beach on Nantucket Sound. It is walkable to Forest Street and Red River Beaches. Swim,...
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    Chatham, Cape Cod 02659
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    • Private Yard
    • Central Heating
    • DVD Player
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fabulous opportunity to rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28. Forest Street Beach on Nantucket Sound, a little piece of heaven, just 5/10th's of a mile, +/- down the street. This charming, upscale beach house has been beautifully updated...
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    South Chatham, Chatham 02659
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Private Contemporary Cape Set on a Hilltop1 / 20
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2016
    We are a family of four travelling from the UK and stayed at the property for one week in July. Chatham was a relaxing week after our whirlwind tour of Florida and New York. We...
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    About this property
    You will enjoy easy times in this 3 bedroom 2 bath Cape set on a hilltop. This very well-equipped house is at the end of a cul-de-sac and offers complete privacy, a large deck with grill, outdoor shower, and ample parking. It has a contemporary open and airy floor plan with cathedral ceilings and...
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    Chatham, Cape Cod 02633
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Spectacular Waterfront Townhome - Oyster Pond #321 / 14
    (5)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Wi-Fi
    • Balcony
    • Porch
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    • Patio
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 21, 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...
    Reviewed February 17, 2017
    Our family visited Chatham numerous times over the years. We stayed at Chatham Bars Inn, Wequassett Resort, and other rentals. By far, Oysterpond Townhome Unit 32 was the best...
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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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    Chatham, Cape Cod 02633
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    • Outdoor Dining Area
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    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this adorable, classic 2 bedroom and 1 full bath Cape beach cottage only a 10 minute walk to Nantucket Sound beaches. Amenities include dishwasher, washer/dryer, one window air conditioning unit, cable TV (with basic cable) with VCR & DVD, microwave, board games, children's books and videos,...
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    South Chatham, Chatham 02659
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Adorable doll like house very light airy cape vintage. Three bedroom one full bath . Close to beaches shopping baseball fields in beautiful historic town of chatham. All linens and towels professionally done like an inn. Vintage house so cute. Full kitchen dinning room living room with fireplace...
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    Chatham, Cape Cod 02633
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Porch
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
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    South Chatham, Chatham 02659 1525
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Parking
    • Internet Access
    • Patio
    • Satellite TV
    • Balcony
    • Air Conditioning
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy our spacious 3-bedroom, 2.5 baths home that is just a short walk to Forest Beach and the warm waters of Nantucket Sound. Our home is located on a quiet lane 0.4 mile to the beach, 0.5 to the Cape Cod bike trail, and less than 4 miles to shopping and eating in quaint Chatham Center and...
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    South Chatham, Chatham 24151
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Terrace
    • Balcony
    • Grill
    • Housekeeping Included
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming ranch is great for two families. Home has 3 bedrooms plus a bunk room, 2 baths, and is wheelchair accessible. The expanded Master Bedroom, en suite and hallway bathrooms, and kitchen are all newly renovated. The living room and Master Bedroom have new wide-screen HD TVs, and the house...
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    Chatham, Cape Cod 02633
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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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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    • Children's Pool
    • DVD Player
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 17, 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 July 17, 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
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Spectacular Waterfront Townhome - Oyster Pond #311 / 13
    (7)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Grill
    • Outdoor Dining Area
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 20, 2017
    The location on Oyster Pond in Chatham is amazing, with close proximity to beaches and the attractions of the town center. The newly renovated unit is sparklingly clean and...
    Reviewed June 28, 2016
    This was the most perfect house for our vacation. It really is beautiful with every facility you could possibly want. Everything in the property details is as described but even...
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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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    Chatham, Cape Cod 02633
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Chatham Cape Cod-Walk to Beach-Location!!1 / 15
    (6)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Internet Access
    • Grill
    • Patio
    • Washer
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The owner's have everything you would need. The cottage is in a fantastic location. We walked to the beach. We played tennis, we took outdoor showers which is always a treat...
    Reviewed June 3, 2017
    The neighborhood is quiet and the walk to the beach very easy. I loved the cottage feel, and the warm personal touches. We had everything we needed for my son and I. Maraide is...
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    About this property
    DISCOUNTED WEEK: July 15-22, only $1800/wk!! (normally $1900/wk) OWNER'S FEES Explanation: It includes $150 cleaning fee + $300 FULLY REFUNDABLE security deposit. 99% of visitors pay $1950, not $2250. (This site states $450 but neglects to state that $300 of it is fully refundable.) OFF SEASON...
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    Chatham, Cape Cod 02659
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to "Keepin' it Reel" on Landing Lane in Chatham a 4 bedroom, 3 bath family friendly Cape Cod Vacation Rental Home that sleeps 9 and is Budget Friendly too! Peak Summer Weekly Rates:  last week of June until the first week in September: $3,500/week. Enjoy this 4 bedroom, 3 bath Cape Cod...
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    North Chatham, Chatham 02650
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Air Conditioning
    • Patio
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    • Wi-Fi
    • Private Yard
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location!! New, lovely furnished home in a quaint little Cape Cod village off Main Street. Minute(s) walk to shops, restaurants, movie theater, library, Chatham Bars Inn, Oyster Pond, Claflin Landing and Lighthouse Beach. Won't need to get in your car to vacation here! Chatham...
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    Chatham, Cape Cod 02633
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Washer
    • Grill
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous sprawling home on 3 acres is surrounded by 50 acres of conservation land. It is extremely private, very quiet, has its own pond, and plenty of space for sunbathing and outside play, large, expansive decks, lots of room for entertainment inside and out. It is completely equipped with...
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    South Chatham, Chatham 02659
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Spectacular Waterfront Townhome - Oyster Pond #251 / 12
    (5)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Air Conditioning
    • Secure Parking
    • Patio
    • Satellite TV
    • Internet Access
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 2, 2016
    Chatham was a fabulous location and own home 25 was our beautiful home away from home. It had every amenity that we could ask for in the home and outside. It was a great...
    Reviewed October 8, 2015
    We recently celebrated our son's commencement from graduate school and could not think of an "easy" location to travel to over the long Labor Day weekend. We were able...
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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
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
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    • Satellite TV
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    • Balcony
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Chatham vacation rental has four bedrooms and can sleep six adults with two children. Unlike much of its competition, it is very spacious. It has one king bed, one queen bed, two twin beds and one room has a futon that can sleep two children. All bedrooms, as well as most of the house, are...
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    Location Information
    Chatham, Cape Cod 02633
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    44 Cranberry Way Chatham Cape Cod - Venture Inn1 / 34
    (2)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 17, 2017
    With family and friends out for our daughter's wedding in Boston last September we wanted a place immediately afterward for an extended reunion. It was all made possible on a...
    Reviewed April 14, 2017
    My boyfriend and I rented this home with two other couples for a relaxing getaway in our favorite spot on Cape Cod - Chatham!The house was so beautiful and newly renovated...
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    About this property
    Central Air and Pet Friendly! Totally Updated 5 Bedroom Cape Cod Vacation Rental Family Home in Chatham on the way to Cockle Cove Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,600- $4,200/week. Large family? No problem! Can't leave home without Fido?...
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    Chatham, Cape Cod 02633
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Washer
    • Housekeeping Included
    • Air Conditioning
    • Parking
    • Patio
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your perfect vacation starts here in this 2017 renovated 4-bedroom home close to Shore Rd and downtown Chatham. Easy walk to restaurants, shops, Oyster Pond, Chatham Bars Inn, Fishing Pier, playground, and A's ball field. Patio with grill, outdoor shower, huge lawn, half basketball court. Both a...
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    Chatham, Cape Cod 02633
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Grill
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is ideal for groups going to weddings, graduations, memorial services, etc. September, October and November dates available now. Make Summer/Spring 2018 reservations NOW!! only 2 night stay min in Spring and Fall. 4 King bedrooms two with private decks, two twin, three bath home with...
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    Location Information
    Chatham, Cape Cod 02650
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming 4 Bedroom Cape House in a quiet setting that sleeps 10 (5 queen beds). Two good sized family rooms and a spacious back deck provide plenty of space for the family to spread out (complete with outdoor shower) . Easy walk (~ 10 mins) to two beaches (Forest & Pleasant Street). Additional...
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    South Chatham, Chatham 02659
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Kayak Or Canoe From Your Back Door On The Monomoy1 / 16
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Hot Tub
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    • Patio
    • Internet Access
    • Grill
    • Central Heating
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Chatham, Cape Cod 02633
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Summer Hydrangea: Chatham's Truly Exceptional Summer Retreat1 / 23
    (15)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Washer
    • Patio
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Chatham, Cape Cod 02633
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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