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Elder Access Holiday Rentals in Chatham

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    26 Matching Rentals in ChathamView all 379 rentals
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    Chatham Escape 5 min Walk to Beach! Private-Newly Renovated-Hear Waves at Night1 / 47
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Quiet Lakeside Cottage - Ideal for Couple1 / 14
    (16)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
    Kid friendly
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    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. We have been hosting vacationers for 16 years in Florida near Walt Disney...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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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    Chatham CapeEscape! Beach Chic Vacation Rental 5 min walk to beach-very Private1 / 48
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
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    • Grill
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    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 2016
    What a unique & wonderful house in Chatham!  John & Ruby are really superb hosts, very accommodating, making sure we were all set… to our delight, John even texted to let...
    Reviewed 3 May 2016
    Plusses:* Kitchen is fully equiped and the stove is big and of excellent quality.* Showers have a lot of power.* Good size house (big living room, separate dining room, big...
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    About this property
    Completely renovated, this year round quaint Cape Cod open concept 1500 sq ft home has 3 bedrooms, 2 baths with a large two level outdoor deck overlooking beautifully landscaped yard. Sleeps 6-8 comfortably. Up to 10 including a pullout sleeper sofa. All rooms are bright and nicely appointed with...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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
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    • DVD Player
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 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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    • Central Heating
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    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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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    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    • Grill
    • Wi-Fi
    • Balcony
    • Porch
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    • 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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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    • Cable/satellite TV
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    • Grill
    Suitability
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Private Garden
    • Grill
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    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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Housekeeping Included
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    • 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
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Wi-Fi
    • Cable/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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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
    About this property
    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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Parking
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    • Patio
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    • 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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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 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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    Pleasant Forest Shores cottages #2 : So. Chatham1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 September 2017
    I admit I ended up here somewhat by accident, but it was a fortuitous accident. Not only is this small cottage colony (5 cottages) perfectly located to get to a variety of...
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    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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    Location Information
    South Chatham, Chatham 02659 1525
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    • 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 #311 / 13
    (9)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 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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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Large, Light Home on Monomoy River1 / 28
    (3)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    Did a girls weekend down the Cape and absolutely loved the house! It has so much space and was perfect for 9 girls to sleep comfortably. Tarrant was so friendly and gave us all...
    Reviewed 1 week ago
    Delightful visit with extended family; Tarrant's home was very accommodating for a large group, with well placed rooms for the couples and a fun bunk bed room for the kids--not...
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    About this property
    Perfect family vacation or friend reunion destination -- large, light and airy house sits on the Monomoy River with lots of space on three floors, including full walkout basement with pool and ping pong tables. Eat on the deck and listen to the birds while taking in great views of the river and...
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    North Chatham, Chatham 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Terrace
    • Balcony
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    • 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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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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