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Holiday Rentals in Chatham

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    3 Bedrooms, Sleeps 6Quick View
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    4 Bedrooms, Sleeps 10Quick View
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    3 Bedrooms, Sleeps 8Quick 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 $1,000/week! (Rents Saturday to Saturday during peak season) "Shore Acres", an extra-large historic Chatham...
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    North Chatham, Chatham 02650
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 24
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    6 Bedrooms, Sleeps 14Quick View
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    2017 rental Rate: $7850 including the cleaning fee~~ Off-Season: $3900 per week, including the cleaning fee ~ For 10 people only, lower level not available for Off-Season rentals~~ A large recently renovated 6 bedroom home located in the exclusive Cannon Hill Estates of North Chatham. This location...
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    North Chatham, Chatham 02650
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, Sleeps 6Quick View
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    2017 Rental Rate: $2475 per week including the cleaning fee ~~ Off Season: $1775 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    2017 Rental Rate: $2100 per week including the cleaning fee ~~ Off-Season: $1575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Great four bedroom home located close to Chatham's Bike Trail, and near a fresh water pond. Located at the end of a cul-de-sac with a nice...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 10Quick View
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    Central Air and Pet Friendly! Totally Updated 5 Bedroom Cape Cod Vacation Rental Family Home in Chatham on the way to Cockle Cove Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,600- $4,200/week. Large family? No problem! Can't leave home without Fido?...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick 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 players, Wi-Fi,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 8Quick View
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    Welcome to: Salty Paws! Pet friendly! Newly renovated- Enjoy this Cape Cod Vacation Rental cottage in Chatham offering 3 bedrooms and 2 baths at the end of a small lane across from the ocean. Wifi and Central AC included (slimline Units). Peak Summer Weekly Rates:  last week of June until the first...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Price Range $1100 - $1300. BOOK BEFORE JUNE FOR $1100 WEEKLY! THAT'S $200 OFF THE REGULAR RATE! NEW LISTING! AFFORDABLE DREAM BEACH HOUSE IN CHATHAM WITH LARGE FRONT AND BACK DECKS, ROOM FOR 6, AND ONLY STEPS TO FOREST BEACH! PET FRIENDLY! There is a dreamlike quality to this 3 bedroom/1 bath...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    2017 Rental Rate $1575 per week, including the cleaning fee! No Off season FRIDAY TO FRIDAY Bright, cheerful home with a peek of Pleasant Bay from the back deck. Swimming in Pleasant Bay is nearby at Jackknife Beach! This charming year-round home is impeccably maintained and has a finished lower...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    4 Bedroom, very bright, beachy home with SEPARATE guest house! This home comes equipped with AC, fully stocked kitchen and deck to enjoy your wine/coffee. Not to mention a private enclosed lawn to relax or play on. Located in the HEART OF TOWN. Walk out the driveway and you will find yourself...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    3 Bedrooms, Sleeps 6Quick View
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    2017 Rental Rate: $2175 per week, including the cleaning fee Off-Season: $1175 per week, including the cleaning fee Enjoy the simple life in this classic, Chatham cottage. Located in the popular Hardings Hills neighborhood, a quick walk down to Hardings Beach! The newly enclosed porch overlooks the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 9Quick 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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    1 Review
    3 Bedrooms, Sleeps 8Quick 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! Peak Summer Weekly Rates:  last week of June until the first week in September: $3,100/week. This Cape Cod Vacation Rental in Chatham has an open floor plan with 3 bedrooms on the main...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 7Quick View
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    Beautiful new condominium nestled on tranquil Perch Pond, located just a half mile from down town Chatham. This unit boast all the amenities of luxury living. Central A/C, gas fireplaces and granite tops to name a few. Spend your afternoons relaxing on the back deck overlooking the pond after a...
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    South Chatham, Chatham 02633
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, Sleeps 12Quick 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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    3 Bedrooms, Sleeps 6Quick View
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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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    2 Bedrooms, Sleeps 6Quick View
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    2017 Rental Rate: $1725 per week, including the cleaning fee ~~ Off Season: $1125 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Recently remodeled cottage with central air is close to shopping and restaurants in downtown Chatham, baseball games at Veteran's Field,...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 8Quick View
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    Lovely bright home with waterviews and central A/C in North Chatham ALSO AVAILABLE FOR HOLIDAY VACATIONS! Stunning, beautifully furnished home with central A/C and views of Pleasant Bay! Located in lovely North Chatham, this home is truly a special spot. The reverse floor plan maximizes views and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6Quick View
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    2017 Rental Rate: $1950 per week including the cleaning fee FRIDAY TO FRIDAY RENTAL! ~~ Off-Season: $1400 per week including the cleaning fee !!! Weekly rentals from mid-JUNE to mid-SEPT Charming cottage just steps to Ridgevale Beach. Upstairs addition is fabulous. It has a separate bathroom and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick 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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    2 Bedrooms, Sleeps 5Quick View
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    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 outside shower. Amenities include window AC units in...
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    West Chatham, Chatham 02669
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, Sleeps 6Quick View
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    2017 Rental Rate: $1925 per week including the cleaning fee ~~ Off Season: $1425 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Comfortable home in a wonderful location near Chatham Village! Let the children play in the huge yard or walk the short distance to Chatham's...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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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 a touch of opulence, room enough for 8, and is just over 1 mile to gorgeous ocean beaches and downtown. A huge...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4Quick View
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    2017 Rental Rates ~ In Season, $1125 including cleaning fee No Off-Season Clean rental home located just 1/2 mile to Hardings Beach or Oyster River Boatyard. Fresh paint and furnishings throughout make this small yet comfortable rental a great buy! Good size living room with high ceilings make it...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Come stay at: Misty Meadow! Completely renovated vacation condo on Cape Cod in North Chatham. Enjoy this lovely condo with all amenities including Central A/C mini splits, wifi, and everything new. Peak Summer Weekly Rates:  last week of June until the first week in September: $1,275/week....
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    North Chatham, Chatham 02650
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Welcome to Harding's Beach Hills, where you will find Three Cheers, this charming cottage by the sea! Peak Summer Weekly Rates:  last week of June until the first week in September: $2,000/week. This Chatham Cape Cod Vacation Rental offers ranch style living with A/C units in all 3 bedrooms,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 10Quick View
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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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    3 Bedrooms, Sleeps 6Quick View
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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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    3 Bedrooms, Sleeps 9Quick View
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    2017 Rental Rate: $3625 per week, including the cleaning fee No Off-Season 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 South Chatham. The open floor plan...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    3 Bedrooms, Sleeps 6Quick View
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    2017 Rental Rate: $2475 per 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 appliances and finishing touches. There is a fantastic screened in...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 5Quick View
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    This adorable, updated and meticulously maintained 2 bedroom, 1 bathroom quintessential Chatham vacation cottage has views of Nantucket Sound. This rental is only 2/10ths of a mile to Forest Beach and Pleasant Street Beach. (The rental does not included access to the beach shown in the photos which...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    5 Bedrooms, Sleeps 10Quick View
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    2017 Rental Rate: $5475 per week, including the cleaning fee Off-Season: $3725 per week (4 night minimum) including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Lovely five bedroom home close to town and the beach! It has everything you need: a huge yard for games, central air, updated...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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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) Located just 0.2 miles from the beach, this is an ideal estate for multi-generational families or other large groups to spend time together...
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    North Chatham, Chatham 02650
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    3 Bedrooms, Sleeps 8Quick View
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    2017 Rental Rate: $3300 per week, including the cleaning fee ~~ Off Season: $1800 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Beautifully decorated home on quiet dead-end street. Open floor plan makes it light and bright! Large living room with additional den give...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great location! Oyster Pond & Chatham Village!! At this home you will be just apprx. 500 ft to private Oyster Pond access, 7/10ths of a mile to the the public beach at Oyster Pond and just 6/10ths of a mile to Chatham Village at Cross St. This fantastic home features plenty of great outdoor living...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    2017 Rental Rate: $6250 per week, including the cleaning fee Off-Season $4450 per week, including the cleaning fee The perfect place for a most memorable and rewarding vacation. New owners of this original Morris Island home have brought in all new furnishings and bed sets. The spacious open floor...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Well maintained two bedroom home that sleeps 6. One queen and 2 twins with a pullout in the den. Located in scenic North Chatham. A five minute drive from downtown Chatham, Chatham Bars Inn, the Lighthouse, Chatham Seaside Links golf course and the baseball field which hosts the Cape Cod Baseball...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    338 Seapine Road CHATHAM, ID# 104736 Waterfront 3 bedroom home overlooking Bassing Harbor and Fox Hill with the outer beach beyond. Located on a cul de sac near Eastward Ho! Country Club in North Chatham, the home is a classic Cape in style. Water access for kayaking in Pleasant Bay and beyond....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Welcome to Sea Glass! This Cape Cod Vacation Rental home is just .2 miles from Pleasant Street Beach in Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,900/week. Warm water, sunsets, and miles of beach on Nantucket Sound awaits you just around the...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • DVD Player
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    • Porch
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    • Parking
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Smoking allowed
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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: $2,200/week. Offering Central AC & Wifi - like most of our Cape Cod Vacation Home Rentals - with over 1600 sq. ft. of finished...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Pet friendly
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    Smoking allowed
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    Welcome to: Endless Summer. Views-Views-Views! Pet Friendly Cape Cod Vacation Rental home with rooftop deck is just .2 to Ridgevale Beach. Peak Summer Weekly Rates:  (last week of June until the first week in September) $4,050/week Pet friendly! Enjoy water views from the main floor living areas...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Grill
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Rental Rate: In Season, $3175 per week, including the cleaning fee No Off-Season Weekly rentals from mid-JUNE to mid-SEPT 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...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Price Range $2500-$5500 Superb Chatham location in Retreat style setting, this expansive home accommodates up to 10 guests in delightful comfort. This exceptional home set on 2.4 acres with pond views and pond access, lush yard with adventurist zip-line, seating surrounded fire pit, basketball...
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    South Chatham, Chatham 2659
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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