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Chatham House Rentals

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    397 Matching Rentals in ChathamView all 428 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate $3875 per week, including the cleaning fee Off Season, $2725 per week, including the cleaning fee Light and bright, this spacious beach home is located right down the street from family-friendly Hardings Beach. Plenty of room to spread out and relax as you enjoy your Chatham...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    On the Water! With Central Air and Wireless Internet-Pet Friendly too. Pet friendly for Dogs only-ask your rental specialist for details. This Cape Cod Vacation Rental home in North Chatham has expansive views of Pleasant Bay from both a lower and upper deck, both living areas, the dining room and...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    151 Sky Way Chatham Cape Cod1 / 43
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Waterfront & Dog friendly! Sleeps 8! This newer Cape Cod Vacation Rental home in Chatham offers panoramic views and backyard access to beautiful Blue Pond and deeded access to White Pond, perfect for swimming, kayaking, canoeing and fishing. Comfort and convenience inside and out define this home,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Walk to Ridgevale Beach From Family Friendly Home1 / 23
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    This bright and airy family-friendly home is just a 1/2 mile walk to this fabulous sandy beach where you can enjoy swimming both on Nantucket Sound or in the milder waters in the adjoining tidal creek. Ridgevale Beach is one of Chatham's most popular destinations for vacationing families. A clean,...
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    West Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    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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    Private Contemporary Cape Set on a Hilltop1 / 20
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $3100 per week including the cleaning fee ~~ Off-Season: $2700 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Boater's Delight!! Beautiful views of Ryder's Cove, a picturesque saltwater inlet in North Chatham. The rental property has a 120' deep-water...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautiful sunsets in Chatham!1 / 20
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Enjoy this spacious home on the Monomoy River with glimpses of Pleasant Bay. Recently renovated, our home boasts a gourmet kitchen with granite counters, 6 burner Wolf cooktop and Sub Zero refrigerator and wine frig . Extra bonus: a second dishwasher and frig in the laundry room offof the kitchen!...
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    Chatham, Cape Cod 02148
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Chatham Family Compound Sleeps 16 Walk to Beach – Linens Included Peak Summer Weekly Rates: $13,500 - $13,900 Rents Saturday - Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home Located just 0.2 miles from the beach, this is an ideal estate for...
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    North Chatham, Chatham 02650
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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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
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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    When only the best will do, head straight to this indulgent 2BR/2BA vacation rental in North Chatham, where high-end furnishings and an inviting outdoor haven offer a vacation experience that’s second to none. Inside, find granite countertops and stainless steel appliances in the kitchen and...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    14 Capri Lane Chatham Cape Cod1 / 28
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Coastal, seaside home offering Central air has plenty of room for 3 couples or 2 families. Walk to beach and town! This Cape Cod Vacation Rental in Chatham has an open floor plan with 3 bedrooms on the main floor and a fully finished lower level game/family room with extra sleeping. Deeded access...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    2018 Rental Rate: $7,650 per week, including the linen/cleaning fee Off-Season: $4650 per week, including the linen/cleaning fee Fabulous home in a great location! About one mile from the village, and Oyster Pond Beach, it is also steps to deeded access to Oyster River and Stage Harbor for boating...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2018 Rental Rate: $1650 per week, including the cleaning fee~~No Off-Season Updated and light two bedroom home, on Hitching Post Rd near the ball field and the playground! Great yard for kids to play while you enjoy spending time in the sunroom! It is a short walk to the Rotary at the beginning of...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    2018 Rental Rate: $2225 per week including the cleaning fee ~~ Off-season $1525 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming home located in terrific central area of North Chatham. Walk to Ryder's Cove boatyard. Beautifully landscaped, fenced-in, private...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Stay in the heart of Chatham, close to all of the activities and attractions. This two-story 4BR/2BA classic Cape-style home is just one mile from Oyster Pond Beach. You’re also 1.5 miles from downtown Chatham, bustling with shops, bars, and restaurants. Spend time enjoying Mother Nature—nearby...
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    North Chatham, Chatham 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Light & Bright Chatham Home, Walking Distance to Beach Linens Included, Pets Considered Peak Weeks - $2,000 Rents Saturday - Saturday during peak season Please note:  This property is part of a larger estate, and is only available to rent individually in the months outside of July and August...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    2017 Rental Rate: $2070 per week, with the cleaning fee~~~ Off Season: $1300 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Comfortable home in Chatham, near Ryder's Cove. Newer furniture throughout and brand new hardwood floors for the 2017 season! Upstairs family...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome to Sea Mist! Spacious Cape Cod Beach House with Central AC and WiFi. Steps to the ocean with deeded access to private beach. Relax and unwind at this 3 bedroom, 2 bath home in Chatham sleeping 6. Enjoy the decks, outdoor shower, and especially the hot tub! Light, bright, and airy. This open...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    Spend the summer on one of Chatham's most exclusive streets in this beautiful home. Located close to the beach, and to Main Street Chatham, the property at 61 Shore Road will please any discerning traveler. Graciously appointed with six bedroom and five full bathrooms, this home is well suited to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 13
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    2017 Rental Rate: $1775 per week, with the cleaning fee No off season rentals Comfortable 4-bedroom home with new appliances, and a new 40' flat screen TV! Farmer's porch and deck with a great view of the stars and sunsets. It also features a newly expanded patio for outside dining, with a new...
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    Chatham, Cape Cod 02669
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    2017 Rental Rate: $7000 plus a mandatory $300 cleaning fee for one week, and $450 cleaning fee for a two week lease ~~ Off-Season: $4000 per week, plus same cleaning fees as above. Weekly rentals from mid-JUNE to mid-SEPT Fabulous renovated Cape located in the heart of Chatham with water-views from...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Take in panoramic views of the shimmering Atlantic from this 4-bedroom, 2-bath luxury house beside a beautiful wetlands conservation area. Built on Chatham's highest point, the house has incredible views, a touch of opulence, room enough for 8, and is just a 2 minutes from gorgeous ocean beaches...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $6450 per week, including the cleaning fee This recently renovated antique farmhouse is filled with upscale furnishings and is practically in the center of town! Located on large lot, it offers a wonderful mixture of new and old. There is one bedroom on the first floor with a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    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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    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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    Why not stay at our Chatham home this summer? Peaceful and inviting, our cape-style home is in a very picturesque area of Chatham. Come relax in our breezy screened porch or enjoy the warm Nantucket Sound waters of Pleasant and Forest Beaches which are a five minute walk (3/10 mi). Leave your car...
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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 9 Quick View
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    2017 Rental Rate: $7840 per week, including cleaning and linens ~~ Off Season Rate: $5540 per week including cleaning and linens $1500 Mandatory Security Deposit Weekly rentals from mid-JUNE to mid-SEPT This Lovely antique home overlooking the Oyster Pond Harbor has just completed a fabulous...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Welcome to: Seaside Stroll! Beachfront Condo! 3 Bedrooms, sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outermost Harbor, Little Beach, or bike up to the village of Chatham. Easy bike ride to Lighthouse Beach and Monomoy Wildlife Refuge!  Central AC...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Our highly rated & reviewed 3 bedroom 1 & 1/2 bath home is nestled on a quiet side street just 3/10 tenths of a mile from one of the best beaches in Chatham...Forest Beach. Our comfortable home is 1100 square feet; and is updated & modern with Air Conditioning, Wi-Fi & a 50'' LCD TV... yet it...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    Water Views Near Chatham Light, Guest Apartment, Sleeps 11 (Linens Included) Pets Considered Peak Summer Weekly Rates: $7,500 - $8,700 Rents Saturday to Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home This classic home is perched in the dunes of Chatham,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Enjoy Family Tides, this pet friendly, updated, 4 bedroom home sleeps 10. Walk to Harding's Beach with deck and outdoor shower. A/C units. Wifi too. Walk to Harding's Beach from this Cape Style home! Enter into the open dining room with seating for 6-8 + 2 at the breakfast bar. One step down and...
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    West Chatham, Chatham 02669
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4BR South Chatham House in Cape Cod!1 / 25
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Begin your Cape Cod adventure by staying in this beautiful 4-bedroom, 3-bathroom saltbox home. Surrounded by natural beauty and close to everything the Cape has to offer, this home is a perfect choice for a group of friends traveling together or a family getaway. Your whole group will love calling...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2017 Rental Rate: $2375 per week, including the cleaning fee ~~Off-Season: $1675/week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Light and bright cottage just steps to the warm Nantucket Sound waters of Pleasant Street Beach! Tasteful, traditional furnishings throughout....
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2017 Rental Rate: $2600 per week, including the cleaning fee ~~Off-Season: $1400 per week, including the cleaning fee Pet Friendly! Weekly rentals from mid-JUNE to mid-SEPT Spacious four bedroom home in quiet neighborhood near town. Path to a small private beach on Lovers Lake too! Plenty of space...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Nestled in a private garden setting a delightful 3 bedroom / 1.5 bath home in Hardings Beach Hills is available to rent this season. With access to Buck's Creek flowing to Nantucket Sound, you can launch your kayak, fish or crab from the private association neighborhood dock and picnic area just...
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    Chatham, Cape Cod 02669
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Dog Friendly! Newer Cape Cod Vacation Rental home with private guest house located near Eastward Ho Country Club, Crows Pond, and Jackknife Beach on Pleasant Bay. Sleeps 10.  Central AC and WiFi too. Welcome to Hydrangea Way! This Chatham family compound is set on a lovely landscaped setting with...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2017 Rental Rate ~ $3050 per week including the cleaning fee. ~~ Off-Season: $2200 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This recently renovated four bedroom beach cottage is in the heart of the beautiful and kid-friendly Hardings Hills area. It offers a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2018 Rental Rate: $3190 per week, including the cleaning fee~~ ~~ Off-Season: $2240 per week, including the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT Bright, spacious 3 bedroom home located in South Chatham, close to the Pleasant Street Beach. This home is a perfect set up for a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2017 Rental Rate: $3925 per week, including the cleaning fee ~~~~~NO Off Season~~~~~ Terrific home on a quiet cul de sac with lots of room for everyone! Enjoy pretty views of Buck's Creek from many windows, and decks...including one on the second floor. Lovely, private outside patio and deck....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly home with central air Comfortable 4 bedroom cape on a quiet street in Riverbay Estates. Convenient to Schoolhouse Pond and Jackknife Cove beach on Pleasant Bay. This home has central air conditioning, an enclosed outside shower, and is PET FRIENDLY. $1600 per week * $100 Handling...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2017 Rental Rates ~ In Season: $3675 per week, including the cleaning fee Off Season: $2675 per week, including the cleaning fee Classic Chatham home, recently remodeled, located in the heart of the village and just steps to Mill Pond! Freshly painted, it features new beds, and furnishings...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    2018 Rental Rate: $2225 per week, including the cleaning fee ~~Off-season: $1525/wk, including cleaning fee Lovely updated cottage located in the popular Harding's Hills neighborhood. Spacious master bedroom with cathedral ceiling and private bath. The kitchen is also updated, light and open. There...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2017 Rental Rate: $2650 per week including the cleaning and linens ~~ Off Season Rate: $2150 per week including cleaning fee and linens Weekly rentals from mid-JUNE to mid-SEPT Bright and cheerful carriage house with beautiful views of Oyster Pond Harbor! Take in the fabulous sunset right from your...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $5225 per week, including the cleaning fee Off-Season: $3925 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT It is all about location! This spacious 3+ BR home, recently renovated, is located across from Oyster Pond and is a quick walk to everything...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    A hidden gem in an unbeatable location, this 4BR/3.5BA home in downtown Chatham puts everything within walking distance. Stroll across the street to Oyster Pond Beach for swimming, lazing on the sand, and spectacular sunsets over the glittering waters. You’re also a short walk from a fantastic...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    2018 Rental Rate: $3200 per week, including the cleaning fee No Off-Season Recently renovated three bedroom home with beautiful views of Red River Marsh and Nantucket Sound! Filled with new furnishings and appliances, this spacious home offers central air, and a huge deck overlooking the water....
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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