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Holiday Rentals in Chatham, MA

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 18
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 27
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2016 Rental Rate: $2175 per week, including the cleaning fee~~ Off-Season Rate: $1675 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Cozy saltbox located only a couple of blocks from Chatham's popular Harding's Beach. The first floor has a spacious bedroom with a... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 1
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2016 Rental Rate ~ $2000 per week, including the cleaning fee Off-Season: $1700 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Spacious 4 BR home on quiet street near Cockle Cove Beach. Lots of living space in this private and centrally located home. Minutes from bike... View all property information
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    South Chatham, Chatham
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    key #39 Additional amenities include: outdoor shower: enclosed, dist. to downtown: 2 miles, fans: 3, area: north chatham, a/c units: 3 - 1 in each br, priceclass: under $3000, year built: 1980, lobster pot, distance to beach: 1 mile or under, name of beach: jackknife beach/pleasant bay,... View all property information
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    Chatham, Cape Cod
    1 / 25
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Price Reduced for Weeks of 7/2 - 7-9, 7/9 - 7/16, 7/16 - 7/23, 8/20 - 8/27 and 8/27 - 9/3 Now $2,900 New Listing. This recently updated 4 bedroom, 2 bathroom home is located in the desirable Stage Harbor area of Chatham. On the ?loop,' this home is just a short walk to Battlefield Landing on Stage... View all property information
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    Chatham, Cape Cod
    1 / 18
    6 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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... View all property information
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    Chatham, Cape Cod
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    2016 Rental Rate: $2425 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT No off-season rentals Comfortable and airy post & beam home located in a quiet neighborhood near Harding's Beach. Tons of windows and skylights throughout bring in the sunlight! The eat-in kitchen... View all property information
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    Chatham, Cape Cod
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    This 3 bedroom, 3 full bath Chatham rental property is located down a quiet dirt road and has some views of Nantucket Sound. Forest Beach on Nantucket Sound is only 7/10ths of a mile away. This home boasts a finished basement with spare bedroom with a twin and futon, updated kitchen for the 2015... View all property information
    Location Information
    Chatham, Cape Cod
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    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Enjoy your vacation and be close to Nantucket Sound at this adorable 2 bedroom cottage only 3/10ths of a mile from Nantucket Sound beaches. This property has one portable AC unit in the Queen bedroom, washer, dryer, digital cable TV (includes sports and weather), DVD player, Wi-Fi, gas grill,... View all property information
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    Chatham, Cape Cod
    1 / 18
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Waterfront on Lovers Lake, 1 AC & WIFI This lovely 3 bedroom, 2 bath ranch features a private, sandy beach right on Lovers Lake (one of Cape Cod's beautiful, glacier-formed kettle ponds); ideal for swimming, or bring your kayak and enjoy the serenity. This property is located down a quiet... View all property information
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    Chatham, Cape Cod
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    $3,600/week Peak Season (July 1- September 2) $1,900/wk for the weeks of (6/24 and 9/2) $1,600/week Shoulder Season (6/17 and 9/9) $1,400/week Shoulder Season (6/10 and 9/16) $1,200/wk (before 6/10 and After 9/23) This light, bright two bedroom two bath Chatham rental cottage has panoramic views of... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 1
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2016 Rental Rate: $2675 per week, including the cleaning fee Off-Season: $1175 per week, including the cleaning Weekly rentals from mid-JUNE to mid-SEPT Lovely, updated condo with water-views of the Nantucket Sound. Light and bright with comfy upscale furnishings. Located on a quiet side street in... View all property information
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    South Chatham, Chatham
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    About this property
    2016 Rental Rate: $1650 per week, including the cleaning fee ~~No Off-Season~~ Light and bright ranch in Chatham's Countryside neighborhood. Hardwood floors throughout, on a nice quiet street. This charming ranch features central air and high speed internet! Located on a wooded lot, with a nice,... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    2016 Rental Rate: $2450 per week including the cleaning fee Off Season Rate: $1950 a week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Take advantage of an easy walk to Hardings Beach from this light and bright updated ranch. The kitchen has been opened up with new... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
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    2016 Rental Rate: $2350 per week, including the cleaning fee ~~Off-Season: $1650/week, including the cleaning fee THIS IS A FRIDAY TO FRIDAY RENTAL 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,... View all property information
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    Chatham, Cape Cod
    1 / 16
    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Situated at the end of a cul-de-sac in a wonderful neighborhood this Chatham home has a very private backyard which abuts conservation land. This 4 bedroom, 2 bath home is also just a half-mile from Nantucket Sound Beaches. Amenities include central AC, washer, dryer, dishwasher, cable TV (includes... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 11
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    2016 Rental Rate: $2800 per week including the cleaning fee Off-Season Rate: $1800 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will love this 4 bedroom home near Ridgevale Beach! Located at the end of a dirt road with water views of a freshwater pond and... View all property information
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    Chatham, Cape Cod
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2016 Rental Rate: $3275 per week including the cleaning fee Off-Season: $1875 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Walk to town in minutes from this recently updated ranch on Highland Avenue! Light and bright with new furnishings throughout, this adorable... View all property information
    Location Information
    Chatham, Cape Cod
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    1 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Views of Nantucket Sound and Bucks Creek from this charming 2 bedroom, 1 bath traditional Cape cottage. Amenities include a window AC unit in the living room, cable TV, Wi-Fi and a charcoal grill. This property has a $75 administration fee, $25 accidental damage protection fee and $85 cleaning fee.... View all property information
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    Chatham, Cape Cod
    1 / 11
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This wonderful 3 bedroom, 2 bath house is in a quiet neighborhood yet is close to shopping, restaurants and beaches. There is access to a nearby path leading to Ridgevale Beach (about 8/10ths of a mile long) and this home is also only a short drive to Hardings Beach. Amenities include window AC... View all property information
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    Chatham, Cape Cod
    1 / 17
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    This is a lovely, recently renovated 3+ bedroom, 2 1/2 bath house within 2/10ths of a mile to popular Ridgevale Beach. Common space abounds with two living areas, a den and a sun room. Every room has recently been painted and the hardwood floors throughout the entire first floor have been recently... View all property information
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    Chatham, Cape Cod
    1 / 13
    4 of 5 stars (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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... View all property information
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    Chatham, Cape Cod
    1 / 9
    6 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    About this property
    2017 Rental Rate: $4525 per week including the cleaning fee ~~ Off-Season: $3025 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Experience a true Old Cape Cod vacation in this rambling home located about 2/10 of a mile from a private beach at Stage Harbor. Great views... View all property information
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    Chatham, Cape Cod
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2017 Rental Rate: $2450 per week including the cleaning fee ~~ Off Season: $1750 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming year-round home, with central air conditioning, within walking distance to the warm waters of popular Ridgevale Beach! Recently... View all property information
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    Chatham, Cape Cod
    1 / 8
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    OWNER VERY NEGOTIABLE... Additional amenities include: outdoor shower: enclosed, dist. to downtown: 2 miles, toaster/toaster oven, 1/2 bath: 1, square footage: 1800, lobster pot, area: west chatham, a/c units: 5- all br's & livingroom, outside furniture, allow pets, number of full and half baths:... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 15
    4.5 of 5 stars (4) Very good
    Private Room, 5 Bathrooms, Sleeps 12 | Quick View
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    • Outdoor Dining Area
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    About this property
    This lovingly restored Greek Victorian former bed and breakfast has 6 bedrooms and 5 full baths. Sleeps 12. Local lore has it that this property was floated over from Nantucket many years ago to its present site. Amenities include a Wolf range, granite counter tops, dishwasher, 2 cable TVs... View all property information
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    Chatham, Cape Cod
    1 / 6
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2016 Rental Rate: $3375 per week including the cleaning fee and linens ~~ Off-Season: $2575 per week including the cleaning fee and linens Weekly rentals from mid-JUNE to mid-SEPT Classic, old-school cape cottage located just steps to downtown Chatham, Chatham Bars Inn, Seaside Links, and Claflin... View all property information
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    Chatham, Cape Cod
    1 / 8
    North Chatham
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    2016 Rental Rate: $3225 per week, with the cleaning fee ~~Off-Season: $2225 per week, with the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT Spacious 5 bedroom on quiet cul-de-sac in prestigious North Chatham. Walk to beach, Band concerts, baseball games, Movies, and fish pier. House has... View all property information
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    North Chatham, Chatham
    1 / 17
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This renovated, adorable antique 3 bedroom, 1 full bathroom Chatham rental home is located in a lovely neighborhood in Chatham Village. It is only 7/10ths of a mile to the shops and restaurants on Main Street in downtown Chatham and even closer (.25 mi) to the Chatham Fish Pier, Chatham Bars Inn as... View all property information
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    Chatham, Cape Cod
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2016 Rental Rate: $2175 per week, including the cleaning fee ~~Off-season: $1525/wk, including cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Lovely updated cottage located in the popular Harding's Hills neighborhood. Spacious master bedroom with cathedral ceiling and private bath. The... View all property information
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    Chatham, Cape Cod
    1 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This turn of the century Chatham rental house is located just 2/10th of a mile from Oyster Pond and 4/10ths of a mile from the downtown area where you can enjoy shopping, fine restaurants, outdoor band concerts, ball games and much, much more. It is a 4+ bedroom, 3 bath property. Amenities for a... View all property information
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    Chatham, Cape Cod
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Views galore from this two bedroom one bath cottage nestled along a saltmarsh only 500 feet from the semi private (association) beach on Nantucket Sound. A perfect getaway for nature lovers and bird watchers. Newly renovated kitchen and interior includes granite countertops, stainless steel... View all property information
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    Chatham, Cape Cod
    1 / 24
    5 of 5 stars (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Enjoy your Cape Cod vacation in this updated, bright and airy 5 bedroom, 3 bath Chatham rental property. This home is located in a lovely setting, with a terrific deck overlooking a saltmarsh. You can be within 4/10ths of a mile to popular Ridgevale Beach and enjoy all the comforts of home with... View all property information
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    Chatham, Cape Cod
    1 / 14
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    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... View all property information
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    South Chatham, Chatham
    1 / 11
    4 of 5 stars (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    This light and bright 3 bedroom, 2 bath ranch cottage is right across the private way from White Pond, a large fresh water pond. There is a private, fully fenced-in back yard with deck and patio, gas grill and enclosed shower. Amenities include central AC, cable TV (includes sports and weather),... View all property information
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    Chatham, Cape Cod
    1 / 13
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2016 Rental Rate: $2275 per week including the cleaning fee Off Season: ~~ $1850 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Spacious 3 bedroom with large yard on cul-de-sac, with deeded rights to Taylor's Pond! This wonderful summer home offers several living... View all property information
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    South Chatham, Chatham
    1 / 12
    5 of 5 stars (5) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Secure Parking
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    • Pet-friendly
    • Child-friendly
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    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... View all property information
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    Chatham, Cape Cod
    1 / 13
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    Wonderful, family-friendly, 5- bedroom house close to town. One ground-floor bed/bath.<BR>Fenced-in, flower filled, back yard with outdoor shower, grille, table and chairs, deck/patio. Walking distance to town or take extra bikes to ride to Lighthouse Beach/ Oyster Pond.<BR>Kitchen table has room... View all property information
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    Chatham, Cape Cod
    1 / 7
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    2016 Rental Rate: $1500 per week, including the cleaning fee~~~NO OFF-SEASON~~~ Enjoy your Chatham summer vacation in this light and bright pet-friendly home on a quiet side street, on the way to Ridgevale Beach, one of Chatham's most popular family beaches! Filled with bright colors and comfy... View all property information
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    Chatham, Cape Cod
    1 / 11
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This Chatham rental home has 3 bedrooms and 1.5 baths. It's situated in a private setting, abutting conservation and convenient to both downtown Chatham and beaches. This property is only 1/2 mile to White Pond, a large fresh water pond which is great for fishing, swimming or paddle boarding.... View all property information
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    Chatham, Cape Cod
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Stay in the heart of Chatham Village in this well-maintained, traditional Cape home. It is only 4/10ths of a mile walk to the shops and restaurants on Main Street in downtown Chatham. This 3 bedroom, 1.5 bathroom Chatham rental home includes window AC units in each of the bedrooms, washer, dryer,... View all property information
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    Chatham, Cape Cod
    1 / 6
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    2016 Rental Rate: $1225 per week including the cleaning fee ~~ Off-Season: $950 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Adorable one bedroom unit just steps to Lighthouse Beach! A quick walk to downtown Chatham for dinner, shopping and more, this charming condo... View all property information
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    Chatham, Cape Cod
    1 / 7
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    2016 Rental Rates: $5800 per week, including cleaning fee Off-Season: $4100/wk, including the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT Location Location Location! This wonderful, family rental is a short walk or easy bike ride into downtown Chatham and offers swimming/sunbathing... View all property information
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    Chatham, Cape Cod
    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    2017 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... View all property information
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    Chatham, Cape Cod
    1 / 11
    5 of 5 stars (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Charming 1 floor cottage with 3 bedrooms and 1 full bath and peeks of Nantucket Sound. There is a large backyard and the beach is less than 500 feet away. Amenities include washer, dryer, dishwasher, cable TV (includes sports and weather) with DVD, Wi-Fi, enclosed outdoor shower, a deck and... View all property information
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    Chatham, Cape Cod
    1 / 11
    South Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    2016 Rental Rate: $3000 per week including the cleaning fee ~~Off-Season: $1700 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Fabulous Cape Cod beach rental located steps from Nantucket Sound with breathtaking views from the huge deck overlooking the marsh and the... View all property information
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    South Chatham, Chatham
    1 / 14
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Lovely five bedroom home close to town and the beach! It has everything you need: a huge yard for games, central air, updated kitchen and an awesome location! The beach is just a walk across the street from this beautifully landscaped Shore Road home. This home is located on the first fairway of... View all property information
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    Chatham, Cape Cod
    1 / 11
    4.5 of 5 stars (12) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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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... View all property information
    Location Information
    Chatham, Cape Cod