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Chatham House Rentals

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    Travellers to Chatham are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    435 Matching Rentals in ChathamView all 466 rentals
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    7 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
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    Historic North Chatham Estate. Sleeps 20, private beach! (linens included) NEW Listing for 2017! Peak Summer Weekly Rates: $13,900 - $16,900 JUST REDUCED -- Remaining Peak Week reduced $2,000/week! Click on the rates tab for updated rates. (Rents Saturday to Saturday during peak season) Please...
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    North Chatham, Chatham 02650
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 24
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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. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,000-$3,200/week. Special deal $1275 off season! Relax and unwind at this 3 bedroom,...
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    South Chatham, Chatham 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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    2017 Rental Rate ~ $1650 per week, including the cleaning fee Off-Season: $1200 per week, including the cleaning fee Comfortable summer rental home in a great central location! This three-bedroom ranch sits on a quiet street located in West Chatham. Just a quick drive in one direction to spend the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    201 Main Street Chatham Cape Cod - Sandpiper1 / 38
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Experience the Sandpiper! Pet Friendly! Nothing beats this luxury 4 bedroom, 4.5 bath Vacation Rental located in the heart of Chatham's historic village!! Peak Summer Weekly Rates:  last week of June until the first week in September: $9,400/week BONUS :LINENS INCLUDED IN SEASON. Whether you are...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Enjoy "Summer Remedy" this traditional, updated Cape Cod Vacation Rental home in Chatham is located just a short walk to Ridgevale Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,300/week Wifi and Central air.  Enter the front door into Living Room with...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Immaculate Chatham Village Renovation, Walk to Beach & Village Peak Summer Weekly Rates: $7,900-$8,800 (Linens Included) (Rents Saturday to Saturday during peak season) JUNE Special - week of June 24th just dropped to $7,500! Your quintessential Chatham vacation awaits! This masterfully restored...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate ~ $5225 per week, including the cleaning fee ~~ Off-Season: $3725, including the cleaning fee~~Weekly rentals from mid-JUNE to mid-SEPT Gorgeous home located in a secluded yet convenient area of Chatham and overlooking Oyster Pond. The house is almost surrounded by water views!...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2017 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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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $2175 including the cleaning fee ***SPECIAL FOR 8/26 Week $1775 inc. Cleaning!!***Off-Season: $1575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Lovely home, on 1/2 acre wooded lot, only 1/2 mile to the warm waters of kid-friendly Ridgevale Beach!...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Come stay at: Seashell Beach Cottage! Beach front vacation rental cottage in Chatham! Peak Summer Weekly Rates:  last week of June until the first week in September: $2,800/week. Stay at this 2 bedroom cottage located right on the beach in Chatham, the best of Cape Cod. Beautiful views! Perfect for...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Welcome to: Cape Cranberry! Quintessential Cape Cod Vacation Rental Cottage in Chatham on the way to Cockle Cove Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $1,400/week. Enjoy this Cape Cod beach cottage with casual coastal decor. A/C units in living area...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Chatham Village Classic, Behind Lighthouse (Pets Considered) Peak Summer Rates: $5,300 - $5,500 (Rents Saturday to Saturday during peak season) This grand Chatham Village family home is located in Chatham, right near the Lighthouse.This vintage antique house has 5 bedrooms, and a premier village...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    • Porch
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    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, 2 Bathrooms, Sleeps 8 Quick View
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    Comfortable 3 bedroom, 2 bath quiet summer retreat only a half mile to downtown Chatham! Peak Summer Weekly Rates:  last week of June until the first week in September: $1900-$2,000/week. Offering Central AC & Wifi - like most of our Cape Cod Vacation Home Rentals - with over 1600 sq. ft. of...
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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 10 Quick View
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    2017 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    16 SEA STRAND LANE (ID#109551) CHATHAM Charming and comfortable! Located in a quiet area within a short driving distance to both Hardings and Ridgevale Beaches. Air conditioning cools the home with units in every bedroom, including first floor master bedroom. WiFi, outdoor shower, washer/dryer,...
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    West Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    2017 Rental Rate: $4150 per week including the cleaning fee ~~ Off-Season: $3175 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, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2017 Rental Rate: $2775 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...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Come Stay at: The Crow's Nest! Pet Friendly! Spend Lazy summer days at this Cape Cod Vacation rental in Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,400/week. With the shade from the pines, the spray of sea salt from the Nantucket Sound and the warm...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Whether you're settling in for a sun-filled beach vacation or seek a quiet seaside escape over the cooler months, this picturesque 3-bedroom, 2-bathroom home promises a charming and relaxing stay on the Cape year-round. Beautiful pine floors and old-world wood furnishings are set off by soft,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $2150 per week, including the cleaning fee Off-Season: $1525 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Spacious three bedroom ranch in quiet neighborhood near Hardings Beach. Recently updated, it is filled with comfortable furnishings and has...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    195 Cedar Street Chatham - ID# 106000 Location, location, location! Only a half mile to the beach at Oyster Pond and 3/4 mile to the Village of Chatham. Located on the Chatham Loop, this is a wonderful newly renovated home including a fabulous new kitchen with sunny breakfast nook. Living room,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    **Just Reduced ~ Week of 8/26 - 9/2 for $1,000** Enjoy this updated 2 bedroom, 1 bath Chatham vacation cottage with views of Oyster River. The open kitchen, dining and living room has a slider leading out to a large deck with chaise lounges, dining table with umbrella, gas grill and enclosed...
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    West Chatham, Chatham 02669
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Charming renovated home with central a/c in North Chatham! Charming renovated home in North Chatham, approx. .5 mile to Chatham Fish Pier, less than 2 miles to Chatham Lighthouse Beach and convenient to Scatteree Beach and the Cow Yard Landing! Approx. 1 mile to Main St., Chatham for shopping,...
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    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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. Peak Summer Weekly Rates:  (last week of June until the first week in September) $2,650 Walk to Harding's Beach from this Cape Style home! Enter into...
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    West Chatham, Chatham 02669
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $2575 per week, with the cleaning fee~~~~Off-Season: $1775 per week, with the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT Updated, light & bright home located about 1/2 mile from downtown Chatham & Oyster Pond. New kitchen and furnishings throughout, as well as a newly...
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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 12 Quick View
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    2017 Rental Rates: $5250 per week, including the cleaning fee FRIDAY TO FRIDAY Rental. ~~ Off-Season: $2750 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Gorgeous beach house on a quiet street just steps to Ridgevale Beach! "Beachy" decor and furnishings throughout!...
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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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    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 Harbor and only 1 mile to the shops and restaurants in downtown Chatham or to the warm waters of Oyster Pond. This...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Welcome to The Cape Escape! Walk to Hardings Beach from this Chatham Vacation Rental Home. 4 Bedrooms, sleeps 8. Access to association dock and picnic area in Harding's Hills Association.  A/C units in 3 bedrooms and the main living area- there is cable and Wifi too.​ Peak Summer Weekly...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    17 Palmer Drive Chatham Cape Cod - The Little Caper1 / 27
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Welcome to The Little Caper. This updated 4 bedroom, 2 bath vacation rental home in Chatham is well maintained and a great spot for making family memories. Just under a mile to town, this coastal Cape is located in a quiet, family neighborhood. The home offers open living with plenty of space to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Enjoy the downtown location of this Cape Cod Vacation Rental Home in the village of Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,500-3,950/week. Convenient to Chatham shops, restaurants, new Orpheum movie theatre and Oyster Pond. Families love the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $4225 per week, including the cleaning fee ~~~Off Season $3225 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will LOVE this beautiful home located in the Bailey's Path neighborhood, a lovely year round residential complex. The house is filled...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    #601 - The Salty Seashell: Great Holiday Deal! Beautiful private Chatham home in great location with a deck, patio, grill & yard!  You will fall in love with this bright and cheery Cape! Wide planked Pine Hardwood floors in Living room and Dining room. Wide Galley Kitchen, fully equipped, including...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    2017 Rental Rate: $5350 per week, INCLUDING linens & cleaning! ~~ Off-Season: $4900 per week including linens & cleaning! Weekly rentals from mid-JUNE to mid-SEPT Gorgeous home in secluded North Chatham neighborhood. The home features hardwood floors, WiFi and central air conditioning with upscale...
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    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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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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    Enjoy a timeless beach vacation in this lovely Chatham home, 3-bed 2-bath, set near the beach with beautiful private gardens. Here, you’re only a mile from the beach, close to biking trails, and surrounded by fishing opportunities. Not to mention the shops and restaurants on Main Street! There’s a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    This recently renovated and expanded 3 bedroom, 2 bathroom home offers fantastic sea breezes and views of Nantucket Sound. The living room and queen bedroom also have views of the water. The new kitchen is bright and functional with granite countertops and a large separate dining area. The new...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    This Cape Cod Vacation home rental in Chatham is just yards out of the back door to Forest Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,850/week. Central AC for those hot summer nights. You can smell the salt water from this ranch-style home with four...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    255 Tanglewood Drive CHATHAM Just a short drive to many salt water beaches and fresh water ponds, as well as both downtown Chatham and Harwich Port, this house is convenient indeed! The backyard is fully enclosed and offers a great place to relax and grill after enjoying all the many things this...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Experience Cape Cod living at our 4-bed, 2-bath Chatham vacation rental in a quiet, quaint wooded neighborhood. Hop on your bike (or into the car) and be at the beach or downtown Chatham in minutes! The home’s wooded deck/backyard and its finished basement—with a pool table, foosball, playroom and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Located in Chatham, this 4 bedroom 2 bath Cape Cod vacation rental home is only 0.3 miles to Ridgevale Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,800/week. This home has window AC units in the upstairs bedrooms as well as the 1st floor bedroom and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pet Friendly.  Relax in this 3 bedroom, 2 bath Cape Cod Vacation home in Chatham that is convenient to downtown Chatham and beaches. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,500/week. Privacy abounds just off Main Street and the home even overlooks a...
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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 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, 2 Bathrooms, Sleeps 6 Quick View
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    64 Waveland Chatham Lovely home in excellent condition located just a short drive to Hardings Beach. This home has been well cared for and features two separate living areas with DVD players, large flat-screen TV s and expanded cable for Red Sox games. The town landing on Oyster River is just...
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    West Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chatham Cape Cod Waterfront Vacation Rental (10325)1 / 42
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    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 3.5...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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