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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 418 Rentals in Chatham
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    South Chatham Cape Cod Vacation Rental (4861)1 / 23
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    388 Main Street Chatham Cape Cod - The Priscilla House1 / 51
    (1)Excellent
    9 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    Come Stay at: The Priscilla House! Pet Friendly! The Priscilla House is a lovely vacation rental home nestled on Main Street in the charming town of Chatham, Massachusetts on Cape Cod. Walk to town and Lighthouse beach! Sheets and Towels INCLUDED! The renovation is COMPLETE and INCLUDES: Central...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 20
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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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    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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    Chatham Cape Cod Vacation Rental (11507)1 / 11
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Charming, waterview condo in Old Chatham Village directly across from Lighthouse Beach and just a short walk to downtown Chatham. This two bedroom, one bathroom, 2nd floor condo has expansive views of Chatham Harbor, South Beach and the Atlantic Ocean. Recently renovated this condo has new kitchen...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    2018 Rental Rate: $5350 per week, INCLUDING linens & cleaning! ~~ June 23-30 and August 25-September 1: $4400/wk, including linens & cleaning No Off-Season 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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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    2018 Rental Rate: $10,400 per week, including the cleaning fee ~~ Off Season: $7,400 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Fabulous new home close to downtown Chatham! This gorgeous house is located on a quiet street, but is also an easy walk to everything...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    ON THE WATER ... * Beautiful water views! * Back decks open to mesmerizing views of Emery Pond * Hammock and patio furniture chosen for comfort and relaxation! * Direct access to pond from backyard. * Clean swimmable pond. * Bass fishing plentiful! * Gas grill. * 2.5 Blocks from Bike trail...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Come stay at: Starfish Beach Cottage! Find your Pathway to Peace! Waterfront 3 bedroom, 2 bath vacation rental cottage is located right on the beach in Chatham, the best of Cape Cod. Perfect for a relaxing getaway, this cottage is steps away from the sand, and is ready for your vacation! Stroll up...
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    Chatham, Cape Cod 02633
    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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    Lovely home with a/c near Ridgevale Beach RIDGEVALE BEACH 7/10 of a mile on Nantucket Sound!! Comfortably sleeps 10!! Cape Cod Bike Trail 8/10 of a mile away. Located at the end of a cul-de-sac and approximately 2 miles to the Village of Chatham for great dining, shopping, Cape Cod League Baseball...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    73 Main Street, Unit #8 Charming second-story condominium apartment located right across the street from Lighthouse Beach. Views of the beach from deck off the living room. Walk across the street to Lighthouse Beach and also within walking distance to the Village. NO pets accepted. $1500 per week *...
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    Chatham, Cape Cod 02633
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    Brand new custom built beauty in South Chatham with water views (linens included) NEW Listing for 2017! Peak Summer Weekly Rates: $7,400 - $8,900 Rents Saturday to Saturday during peak season Be among the first to vacation at this wonderful custom-built home in South Chatham. Just finished in...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Enjoy fantastic, unobstructed views of Red River Beach and Nantucket Sound from this 3 bedroom, 2 full bath traditional Chatham vacation rental only 1/10th of a mile to a semi-private beach. The property comfortably accommodates 8 people however can take up to 10 with the use of the full-size sleep...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2018 Rental Rate: $1650 per week, including the cleaning fee~~No Off-Season Updated and light two bedroom home, on Hitching Post Rd near the ball field and the playground! Great yard for kids to play while you enjoy spending time in the sunroom! It is a short walk to the Rotary at the beginning of...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 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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    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2018 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 and Kayaking in Pleasant Bay is right down the road at Jackknife Beach! This charming year-round home is well-maintained and has...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Adorable doll like house very light airy cape vintage. Three bedroom one full bath . Close to beaches shopping baseball fields in beautiful historic town of chatham. All linens and towels professionally done like an inn. Vintage house so cute. Full kitchen dinning room living room with fireplace...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Wonderful 4 bedroom, 3.5 bath rental home situated 3/10ths of a mile from Pleasant Street beach and Forest Beach on Nantucket Sound. This home offers plenty of living space with comfortable furnishings. There is a nicely furnished deck for relaxing afternoons or dinner after a day at the beach. The...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome to: Seaside Stroll! Beachfront Condo! 3 Bedrooms, sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outermost Harbor, Little Beach, or bike up to the village of Chatham. Easy bike ride to Lighthouse Beach and Monomoy Wildlife Refuge!  Central AC...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Chatham Cape Cod Vacation Rental (10260)1 / 27
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Spend your Chatham vacation in this beautiful 4 bedroom, 2.5 bath home located 500 feet from Pleasant Street Beach. This is a truly unique, custom home featuring gorgeous woodwork throughout, a first floor master bedroom with Jacuzzi tub, a bright and beautiful kitchen with granite and silestone...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    393 STONY HILL ROAD CHATHAM Charming and completely renovated cottage, 7/10 of a mile to Scatteree Beach and the Cow Yard Landing and under 2 miles to Main St., Chatham for shopping, dining, and ice cream! This adorable one bedroom, air conditioned cottage has vaulted ceilings, exposed beams, a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rates~~$3225, including the cleaning fee Off Season~~$2725 per week including the cleaning fee Gorgeous, updated rental with tons of open living space. This is a great beach rental, within 1/2 mile to Ridgevale Beach. Terrific family neighborhood spot for kids. Light and bright...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    RENOVATED very bright, beachy condo, 2bdrms/2bths. This unit comes equipped with AC, fully stocked kitchen and 2 decks to enjoy your wine/coffee. The decks overlook Little Mill Pound. This condo is located in town and the famed, kid friendly Oyster Beach & Lighthouse Beach are a 10 minute...
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    Chatham, Cape Cod 02633
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    151 Sky Way Chatham Cape Cod1 / 47
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Waterfront & Dog friendly! Sleeps 8! This newer Cape Cod Vacation Rental home in Chatham offers panoramic views and backyard access to beautiful Blue Pond and deeded access to White Pond, perfect for swimming, kayaking, canoeing and fishing. Comfort and convenience inside and out define this home,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    2018 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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick 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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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    2018 Rental Rate: $12,400 per week, including the cleaning fee Off-Season $8800 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This beautiful home on Shore Road is the perfect spot for your Chatham vacation! It offers beautiful furnishings and plenty of space for...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    6 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    $13,500.00/week Peak Season (7/15 - 8/19) $12,500.00/week On Season (7/1 - 7/15 and 8/19 - 9/2) $11,500.00/week Off Season Gorgeous panoramic views of Stage Harbor, Nantucket Sound and Outermost Harbor from every room in the house. Private dock, multiple decks, a swimming pool and an incredibly...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 11
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    Chatham Cape Cod Waterfront Vacation Rental (2683)1 / 36
    (2)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    $13,500/week Peak Season (June 30 - August 31) $9,300/week for the weeks of (6/25 and 9/1) $7,900/week Shoulder Season (6/16 and 9/8) $6,900/week Shoulder Season (6/9 and 9/15) $6,200/week (before 6/9 and after 9/22) Spend your Chatham vacation in this beautiful 4 bedroom 4.5 bath home located less...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, 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, 6 Bathrooms, Sleeps 11
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    Pleasant Forest Shores cottages #2 : So. Chatham1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
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    South Chatham, Chatham 02659 1525
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Welcome to: Salty Paws! Pet friendly! Newly renovated. Enjoy this Cape Cod Vacation Rental in Chatham offering 3 bedrooms and 2 baths at the end of a small lane across from the ocean. Wi-Fi and Central AC included (Slimline units). Walk through the front door and step into the living room, here you...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Come Stay at: Chatterbox! Location! Location! Location! Chatham Vacation Rental home with 3 bedroom, 3.5 bath in the heart of Chatham and sleeps 7. Whether you enjoy cocktails on the traditional front porch, read a good book in the cozy sun room, eat outdoors on the mahogany deck, or take in an...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Get a true dose of nautical charm with this 1-bedroom, 1-bathroom Windmill vacation rental cottage, which sleeps 3. The perfect size and layout for a couple or small family, this Windmill offers all the necessary comforts of home and beautiful views of Oyster Pond for an unforgettable Cape Cod...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    2018 Rental Rate: $1800 per week, including the cleaning fee ----Off Season: $1000 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Cute 3 bedroom ranch, walking distance to town and Oyster Pond. A great new 2nd family room just finished in the lower level! No deck, but...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2018 Rental Rate: $1925 per week including the cleaning fee ~~ Off Season: $1425 per week including the cleaning fee 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 playground. The location is a few blocks...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    2018 Rental Rate: $12,750 per week~~LINENS and CLEANING INCLUDED. ~~ Off Season: $10,950 per week ~~Linens and Cleaning Included WEEKLY rentals only-- no short term leases Elegant, upscale home located in the heart of downtown Chatham. This 5 BR residence keeps the look of its original Victorian...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    52 PLEASANT STREET Easy access to Pleasant Street Beach! This house is close to South Chatham restaurants, Pleasant Street Beach, the Cape Cod Bike Trail and it is just a short drive to both downtown Chatham and Harwich Port. 3 bedrooms and 2 bathrooms allow for a comfortable living set up....
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    Chatham, Cape Cod 02633
    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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    105 Wood Carver Knoll, Chatham - ID# 106342. Spectacular waterfront home in Chatham overlooking Oyster Pond! Central Air, Wireless Internet, gourmet kitchen with espresso machine, Keurig and more. Enjoy the deck with incredible views of Oyster Pond, the church steeples of Main St, tidal marshes and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Chatham  Cape Cod Waterfront Vacation Rental (10354)1 / 25
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Spectacular seaside views from almost every room in this beautiful 4 bedroom, 3 bathroom Chatham rental home which rests below the watchful gaze of Chatham Light. This Chatham rental home is ideally situated between scenic Lighthouse Beach and the edge of Monomoy National Wild Life Refuge, a beach...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    2 Bedrooms, 1 Bathroom, 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, 1 Bathroom, Sleeps 5
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    16 ELLIS Pet friendly home in Chatham sleeps 4. Two bedrooms one with a queen and bedroom two has a queen and a single bed. Outdoor seating on the deck is spacious. Enclosed outside shower. One and a half baths. WiFi. A/C in the bedrooms. A short drive to Harding beach. FRIDAY arrival and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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, 2 Bathrooms, Sleeps 8
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