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Chatham House Rentals

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    Travellers to Chatham are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    354 Matching Rentals in ChathamView all 389 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Chatham Cape Cod Waterfront Vacation Rental (2683)1 / 36
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, Sleeps 6 Quick View
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    Stay in the heart of Chatham Village in this well-maintained 3 bedroom 1.5 bathroom home. Situated in a quiet neighborhood only 4/10ths of a mile from the shops and restaurants on Main Street, baseball field, playground and the Fish Pier. This traditional Cape home features a queen bedroom on the...
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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 9 Quick View
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    Schoolhouse Pond just 1/10 mile! Charming custom remodeled Cape Cod home, 1/10 mile to Schoolhouse Pond Beach--perfect for freshwater beach lovers. First floor offers open kitchen / living area with AC unit and one first floor queen bedroom with a ceiling fan. Second floor has three bedrooms all...
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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 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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    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...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2125 per week Off-Season: $1600 per week If less than one week in Off-Season; $225 per night (plus cleaning & booking fees) Click for More Photos, Map, and Availability Calendar Great four bedroom home located close to Chatham's Bike Trail, and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lounge on our beautiful beaches, experience great fishing or spoil yourself in our unique shops all while staying in this charming, remodeled and finely decorated home close to Red River and Pleasant Street Beaches. This home has 4 bedrooms and 3 full baths. There is an en-suite master bedroom...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This 3 bedroom, 2 bath house is located just .5 miles from Pleasant Street Beach and Red River Beach. This traditional Cape home has one bedroom with full bed and a full bathroom on the first floor and two bedrooms (king and two twins) and a full bath on the second floor. There are two...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3,500 per week Off-Season: $2,200 per week Click for More Photos, Map, and Availability Calendar Light and bright, this spacious four bedroom is walking distance to the warm waters of the Nantucket Sound at Pleasant Street Beach. Take advantage...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    1 Bedroom, Sleeps 4 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1300 per week Off-Season: $1000 per week Click for More Photos, Map, and Availability Calendar Adorable one bedroom unit just steps to Lighthouse Beach! A quick walk to downtown Chatham for dinner, shopping and more, this charming condo is...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Charming 3 bedroom, 1 bath cottage with views of Nantucket Sound from the rooftop deck. Forest Beach is just 2/10ths of a mile away. Amenities include a window AC unit in each bedroom, Wi-Fi, cable TV with basic cable only, DVD player, washer, enclosed outdoor shower, a deck with furniture and a...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Post-and-beam home near beach with modern conveniences & high-end furnishings1 / 35
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Tradition and modern luxuries collide at this lovely Cape Cod home. You'll find high-end furnishings inside and beach access nearby! You're on a quiet lot near a salt marsh and just a half mile from Forest Beach and less than two miles from lovely Taylors Pond. Post-and-beam construction can...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    This 3 bedroom 1 bath rental is located within walking distance to two fresh water ponds and is just a mile from downtown Chatham. Emery Pond is perfect for kayaking while the much larger White Pond is great for swimming and paddleboarding. The bike path is also adjacent to the neighborhood...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 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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    3 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $4,425 per week Off-Season: $3,125 per week Click for More Photos, Map, and Availability Calendar Stunning, new home located on Oyster River with breathtaking views of the river and marsh. Enjoy your afternoons after the beach watching the birds...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3000 per week Call About Off-Season Click for More Photos, Map, and Availability Calendar Fabulous Cape Cod beach rental located steps from Nantucket Sound with breathtaking views from the huge deck overlooking the marsh and the ocean. Airy,...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    West Chatham Cape Cod Vacation Rental (2307)1 / 19
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Enjoy your Cape Cod vacation in this tastefully decorated, comfortable home. It is located in Hardings Beach Hills, only 4/10ths of a mile from popular Harding's Beach. This 3 bedroom, 2.5 bathroom home has an updated kitchen with granite countertops and stainless steel appliances as well as...
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    Chatham, Cape Cod 02669
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Chatham Cape Cod Vacation Rental (30)1 / 14
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Enjoy your Chatham vacation in this 3 bedroom, 2 bathroom house that is only 2/10th of a mile from Pleasant Street Beach on Nantucket Sound. This traditional Cape home features 2 bedrooms on the first floor and 2 bedrooms on the 2nd floor. The living room and kitchen lead to a second light and...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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) 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 January 2017, this...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 9
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    4 Bedrooms, Sleeps 12 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2225 per week Off-Season: $1525 per week Click for More Photos, Map, and Availability Calendar Weekly rentals from mid-JUNE to mid-SEPT Charming home located in terrific central area of North Chatham. Walk to Ryder's Cove boatyard. Beautifully...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    One of the most photographed Wind Mill homes on Cape Cod. Classic old world charm, coupled with all modern conveniences located near the beach and town. The Stony Hill Mill, constructed with 100 year old beams, river rock and barn board, is truly Cape Cod at its finest. This large stately home is...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 9 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2070 per week Off-Season: $1300 per week Click for More Photos, Map, and Availability Calendar 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 9
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    3 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3225 per week Off-Season: $2725 per week Click for More Photos, Map, and Availability Calendar Gorgeous, updated rental with tons of open living space. This is a great beach rental, within 1/2 mile to Ridgevale Beach. Terrific family...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    South Chatham Cape Cod Vacation Rental (4520)1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Spend your Cape Cod vacation sunbathing by the pool at this 3 bedroom, 2.5 bath Chatham vacation rental home. This home is located at the end of a cul-de-sac just 3/10ths of a mile from Pleasant Street Beach and Forest Beach on Nantucket Sound. The pool is surrounded by a spacious, grassy back...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 11 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $8600 per week Off-Season: $6650 per week Click for More Photos, Map, and Availability Calendar This gorgeous home offers over 5000 square feet of living space spanning three levels, and manages to be both elegant and comfortable. It features...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 11
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    Heart Of Chatham Village- Beach, CBI, Main Street1 / 21
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms (King Master w/ Ensuite), 3 Bathrooms, Sleeps 8 - Sofa Sleeps 2 Addl Newly renovated (Spring 2016), quaint and charming in the heart of Chatham Village Center. Enjoy the full benefit of being steps away from the hustle and bustle of Main Street in one direction, or the scenic beaches...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This quaint 3 bedroom, 2 bath house is a quick ride to Jacknife Beach, fresh water Schoolhouse Pond or downtown Chatham. Amenities include central a/c, washer, dryer, dishwasher, Wi-Fi, cable TV (includes sports and weather) and a DVD player. The yard is nicely manicured with a spacious lawn,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 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....
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    South Chatham Cape Cod Vacation Rental (6495)1 / 12
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    This rental property boasts a main house and a fully equipped cottage, great for extended family or friends. The main house has 3 bedrooms, 1 full bathroom, a kitchen/dining area, living room and a charming wrap-around covered porch for relaxing after the beach. There is a queen bedroom and a...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Brand new custom built beauty in Chatham, walk to Ridgevale Beach! (linens included) Peak Summer Weekly Rates: $5,500 - $6,500 Rents Saturday to Saturday during peak season NEW Listing for 2018!  This brand new custom home provides a luxurious vacation experience just a short walk from...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 10 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3725 per week Off-Season: $3225 per week Click for More Photos, Map, and Availability Calendar 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...
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    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Enjoy your summer vacation in this charming 3+ bedroom 2 bath home that is located 7/10ths of a mile to Nantucket Sound beaches. Situated just 2/10ths of a mile to Mill Creek which is a great spot for kayaking and canoeing into Nantucket Sound or Taylor's Pond. Amenities include washer, dryer,...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    South Chatham Cape Cod Vacation Rental (7129)1 / 17
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Just steps away from Forest Beach this 3 bedroom, 3 bath home boasts wonderful views of Nantucket Sound from the three decks, main living area and the two upstairs bedrooms. The first floor den has a queen sleep-sofa and large flat-screen TV. The third bedroom and bathroom are located in an...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    New Listing. This renovated 3+ bedroom, 2 bathroom home is just .3 mile to Pleasant Street Beach. This home is much larger than it appears from the outside thanks in part to the open floor plan, cathedral ceiling, oversized bay window and hardwood floors. The nicely renovated kitchen has a...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    This beautiful, newer 4 bedroom, 3 bath custom home has an expansive deck and custom built patio area with plenty of outdoor seating, a fire pit and both gas and charcoal grills. It is only 6/10ths of a mile to Forest Beach and even closer to a public tennis court and basketball hoop. The interior...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, 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, 1 Bathroom, Sleeps 6
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1,975 per week Off-Season: $1,425 per week Click for More Photos, Map, and Availability Calendar Enjoy the simple life in this classic, Chatham cottage. Located in the popular Hardings Hills neighborhood, a quick walk down to Hardings Beach!...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Located in one of the most desirable areas of Chatham, this 3 bedroom, 2 bathroom classic Cape home is just a short walk to Lighthouse Beach. The spacious first floor master bedroom with queen bed and sitting area opens up to a comfortably furnished deck in a lovely private back yard. You can...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2375 per week No Off-Season Click for More Photos, Map, and Availability Calendar Centrally located, this lovely updated three bedroom home is a wonderful spot for your Chatham vacation! Only one mile from everything downtown Chatham has to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 7
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1650 per week No Off-Season Click for More Photos, Map, and Availability Calendar 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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    South Chatham Cape Cod Vacation Rental (76)1 / 11
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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), DVD player, Wi-Fi, enclosed outdoor shower, a deck and...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $6200 per week Off-Season: $4400 per week Click for More Photos, Map, and Availability Calendar Gorgeous home, recently updated and lovingly decorated. This home features peeks of Oyster Pond from the newly enclosed screened porch, as well as...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Convenient Location, Near Riverbay in Chatham! Open floor plan living, central A/C, 3 bedrooms and 2 bathrooms are just the beginning of what this property offers. Enjoy relaxing on the deck after exploring nearby East Harwich and Chatham. $1600 per week * $100 Handling Fee * Choice of $55...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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