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House 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.
    All 368 Rentals in Chatham
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, Sleeps 6 Quick View
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    Chatham Cape Cod Waterfront Vacation Rental (10325)1 / 42
    (6)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    A traditional Cape Cod pond-front compound set on a beautifully landscaped 2-acre lot with lovely views of Black Pond. Enjoy summer breezes while relaxing on one of the many patios in this very private yard perfect for lawn games, barbeques or simply stargazing. The main home has 4 bedrooms and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates: $2475 per week, including the cleaning fee ~~ Off-Season: $1475 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Bright and cheerful summer cottage, walking distance to the warm waters of Hardings Beach! Located in Hardings Hills, there is also an...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    This 4 bedroom, 2 bath home, located just 3/10ths of a mile from Pleasant Street Beach on Nantucket Sound, boasts a lovely yard with mature plantings that offer both privacy and a peaceful setting, especially while enjoying the deck and the double swing in the back yard. Inside, this home has an...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Chatham Cape Cod Vacation Rental (1936)1 / 13
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    A very well maintained 3 bedroom, 2 bath home located just over 1/2 mile to Ridgevale Beach on Nantucket Sound. There is an open and spacious back yard that is great for games and bbq's. Amenties include central AC, washer, dryer, dishwasher, 2 TVs (includes sports and weather), DVD player,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $1675 per week including the cleaning fee. This is a FRIDAY TO FRIDAY RENTAL. ~~ Off-Season: $1275 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Adorable, updated rental located on a quiet street in South Chatham. New furnishings and fresh paint make...
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    South Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, 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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    South Chatham Cape Cod Waterfront Vacation Rental (1841)1 / 19
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Spectacular panoramic water views from this 4 bedroom, 2 bath Chatham rental situated right on Cockle Cove Beach on Nantucket Sound. This is one of very few homes where you can step out your door and take only a few steps to the water's edge. The living room, dining room, kitchen and a full...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Short Drive to Everything! Our cape home offers lots of space for your family. 3/4 mile to Pleasant Bay Beach, 1 minute walk to Ryder’s Cove boat yard, few minutes walk to tennis courts and Cape Cod bike trail. 5 minutes drive to town center. Close to playground and baseball field - home of the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Breathtaking riverfront dog-friendly home w/ a lovely deck, close to the beach!1 / 29
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Experience a glimpse of Cape Cod waterfront living at this three-bedroom Chatham home, a dog-friendly property with a wrap-around deck, panoramic views of the ocean and Oyster River, and nearby access to Harding's Beach. This quaint two-level home is scenically situated between Nantucket Sound and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rate: $1750 per week, including the cleaning fee ~~ Off Season: $1275 per week, including the cleaning fee Recently remodeled cottage with central air is close to shopping and restaurants in downtown Chatham, baseball games at Veteran's Field, and Ryder's Cove. This light and bright...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rates: $4425 per week, including cleaning Off-Season: $3125 per week cleaning Weekly rentals from mid-JUNE to mid-SEPT Stunning, new home located on Oyster River with breathtaking views of the river and marsh. Enjoy your afternoons after the beach watching the birds and wildlife from...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 5 Quick View
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    2018 Rental Rate: $1225 per week, including the cleaning fee. Weekly rentals from mid-JUNE to mid-SEPT Nicely decorated house on a quiet street near town and the Cape Cod Rail Trail. This is a very well maintained and comfortable home with the owner's original artwork throughout. Small yard in...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, Sleeps 5
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    3 Bedrooms, Sleeps 6 Quick View
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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, Sleeps 6
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    6 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    209 Champlain Rd Chatham MA DOG FRIENDLY Great, rambling home with an old-Cape Cod feel located on the 'loop' just around the bend from Stage Harbor. Wonderful area to enjoy while here on the Cape! A tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 11
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    South Chatham Cape Cod Waterfront Vacation Rental (6972)1 / 14
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    This 3 bedroom, 3 bath Chatham home has multiple decks overlooking Mill Creek, the salt marsh and Nantucket Sound. Stairs leading to the creek allow you to launch a kayak or paddleboard and paddle into Nantucket Sound right from the property. The house is only .5 mi walk or drive to Cockle Cove...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    11 JEANETTE DRIVE Just over a mile to downtown Chatham and also close to Hardings Beach and Oyster Pond! This great house is convenient to the bike trail, tennis courts and has deeded rights to a fresh water pond! With four bedrooms and two full baths, this updated home comfortably sleeps up to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Charming 3 bedroom, 1 bath cottage with views of Nantucket Sound from the rooftop deck. There is a good sized backyard and Forest Beach is just 3/10ths of mile away. Amenities include a window AC unit in each bedroom, cable TV (with basic cable only; no NESN, ESPN, Weather Channel, etc.) with a DVD...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Waterfront cottage on Nantucket Sound. Enjoy the spectacular location and panoramic waterviews from this 6 bedroom, 2 bath Chatham rental cottage situated right on Cockle Cove Beach on Nantucket Sound. This is one of very few cottages where you can step out your door and take only a few steps to...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Chatham Cape Cod Vacation Rental (993)1 / 17
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This brand new Chatham home is conveniently located only 6/10ths of a mile from Forest Beach. The gleaming hardwood floors and open floor plan give this home a light and airy feel and the dining area opens to a spacious furnished deck for relaxing afternoons or an alfresco dinner after a long day...
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    Chatham, Cape Cod 02659
    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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    Enjoy your summer vacation in this charming 3 bedroom, 2 bath home that is located 7/10ths of a mile to Nantucket Sound beaches and just 2/10ths of a mile to Mill Creek which is great for kayaking and canoeing into Nantucket Sound or Taylor's Pond. Amenities include central AC, washer, dryer,...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This recently renovated 4 bedroom, 2 bath house has a bright open floor plan with new furnishings throughout. This comfortable home is situated in a wonderful neighborhood with a great yard for children and is only 5/10ths of a mile from Nantucket Sound Beaches. A queen bedroom and a twin bedroom...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 12 Quick View
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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, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Enjoy this 3 bedroom, 2 bath Chatham home just minutes from the Cape Cod Rail Trail. The first level of the home features a kitchen with beautiful granite counter tops, separate dining area, living room and a Suite with a full sized bed and full bathroom. The second level has two additional...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Bedrooms, 11 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
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    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 friends...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 8 Bedrooms, 11 Bathrooms, Sleeps 16
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    5 Bedrooms, Sleeps 11 Quick View
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    2018 Rental Rate: $8600 per week including the cleaning fee Off Season: $6650 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This gorgeous home offers over 5000 square feet of living space spanning three levels, and manages to be both elegant and comfortable. It...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 11
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Cute cottage only 1 mile to Hardings Beach! 2 bedroom, 2 bath Cape Cod Cottage! Well maintained and appox. 1 mile to Hardings Beach in Chatham. Relax and dine in the screened porch which expands across the front of the cottage. This neighborhood is located off Barn Hill and a short distance to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 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, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Located in the heart of Chatham Village with its many delightful shops, galleries, and restaurants this 2 bedroom home is close to everything Chatham has to offer. Enjoy a short stroll to Lighthouse Beach, the Chatham Fish Pier, tranquil Mill Pond or the Orpheum Theatre. The first floor offers a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Porch
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    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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    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    2018 Rental Rate: $3625 per week, including the cleaning fee Off-Season: $2525 per week, including the cleaning fee Wonderful waterfront home, right on Taylor's Pond! This spacious home is light and bright, filled with upscale furnishings, colorful decor, and offers a private, peaceful setting in...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    4 Bedrooms, Sleeps 10 Quick View
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    2018 Rental Rate: $4450 per week including the cleaning fee ~~ Off-Season: $3150 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Great family rental home, within walking distance to the warm waters of kid-friendly Hardings Beach! There is sleeping for 10 people,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    Cape Cod / Chatham HISTORIC FAMILY ESTATE1 / 8
    (2)Excellent
    9 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    Southwesterly ocean breezes flow over this HISTORIC family estate built in the 1930?s by Mr. & Mrs. John Peale Bishop, a classmate and best friends at Princeton of F. Scott Fitzgerald and himself a famous writer and poet. The Gatsby sits on 1.3 acres in Chatham overlooking Nantucket Sound....
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    South Chatham, Chatham 02659
    Holiday Rental House - 9 Bedrooms, 4 Bathrooms, Sleeps 20
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    $2,800/week Peak Season (6/30 - 8/24) $1,500/week Shoulder Weeks (6/23 - 6/29 and 8/25 - 8/31) $1,400/week Off - Season (6/9 - 6/22 and 9/1 - 10/12) This upgraded and very well maintained 4 bedroom, 3 bath cape style home is situated on a cul-de-sac 8/10ths of a mile from Cockle Cove Beach....
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rate: $1700 per week, including the cleaning fee Off Season: $1150, including the cleaning fee Charming and updated ranch, located in a quiet neighborhood but is also a quick drive to the warm waters of Cockle Cove Beach! This light and bright ranch, features comfortable furnishings,...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    Chatham Cape Cod Vacation Rental (102)1 / 19
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    $7,200/week Peak Season (7/21 -8/17) $6,800/week On Season (6/30 -7/20 and 8/18 - 8/31) $5,000/week Off Season (6/23 - 6/29 and 9/1 - 9/7) $4,300/week Off Season (6/16 - 6/22 and 9/8 - 9/14) $3,600/week Off Season (1/1 - 6/15 and 9/15 - 12/31) Spectacular 3+ bedroom, 3.5 bath home in one...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Chatham Cape Cod Vacation Rental (9068)1 / 17
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Enjoy this 3 bedroom, 1.5 bathroom Chatham vacation home in the Harding's Hills neighborhood only 1/2 mile from popular Harding's Beach. There is a bonus 'Florida room' with full-size futon for sleeping or enjoying the afternoon sun. The backyard patio has a great dining table with umbrella, a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Classic old-style Cape Cod home overlooking Chatham Harbor with private stairs leading down to Lighthouse Beach. SUNDAY arrival and departure at this Classic old-style Cape summer house in a simply spectacular location. This 4 bedroom home inside the Old Village Historic District overlooks...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 9 Quick View
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    2018 Rental Rates: IN SEASON: $1800 per week (June 16-Sept 8) ~~Pre-season (May 12-June 16) $1,200 per week ~~Post-season (Sept 8-Oct 12th) $1,200 per week $175 MANDATORY cleaning fee per lease Light and airy - hardwood floors, lots of windows make this beach cottage a great vacation rental! The...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 9
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Enjoy your vacation in this bright, open 3+ bedroom, 2 bath Chatham home on a cul-de-sac in a pleasant neighborhood. This home is only one-half mile to Cockle Cove Beach or 2/10th's of a mile to Taylor's Pond where you can launch a kayak to paddle into Nantucket Sound. New furnishings include a...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Convenient Location, Near Riverbay in Chatham! Open floor plan living, central A/C, 3 bedrooms and 2 bathrooms are just the beginning of what this property offers. Enjoy relaxing on the deck after exploring nearby East Harwich and Chatham. $1600 per week * $100 Handling Fee * Choice of $55...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    This landmark property has the most remarkable views anywhere! After a day at the beach relax and take in one of the prettiest views on the Cape. Three bedrooms, bonus sleeping area, one full and two half baths and on a quiet cul-de-sac, at the very end of the road and sitting on just over an acre...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Enjoy this lovely Chatham vacation rental located in desirable North Chatham near, gorgeous beaches, restaurants & Chatham Village. Here you can enjoy everything Chatham has to offer, from Chatham baseball games, the village area with restaurants & shops, Lighthouse beach & more! Gorgeous...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rate: $2775 per week, with the cleaning fee ~~No Off-Season~~ Take advantage of the quick walk to the Chatham A's Ball Field, the playground and Main Street from this pristine three bedroom ranch! There are two living spaces, great for the kids and adults to be able to spread out. A...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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