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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.
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    4BR South Chatham House in Cape Cod!1 / 25
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Chatham  Cape Cod Vacation Rental (5438)1 / 24
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    About this property
    Enjoy your vacation in this well maintained, bright, contemporary 4 bedroom, 2.5 bathroom Chatham rental home situated in a lovely neighborhood located along the popular Chatham 'Loop' and only 1/10th of a mile to Stage Harbor town landing where you can stroll along the water's edge, kayak, paddle...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome to Tide After Tide. Pet Friendly! Private, Family Ranch-Style Riverbay home in Chatham for your Cape Cod Vacation! Located on a peaceful, residential, dead-end road. As you enter the through the front door you will find comfortable seating in the living room with a flat screen TV. There is...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet Friendly! (for dogs only) Located in a prime in-town location. This Cape Cod Vacation Rental Cottage complex is just steps to the Mill Pond (a saltwater inlet of Nantucket Sound) in Chatham's Old Village and a few blocks to beautiful Lighthouse Beach. This desirable and newly renovated family...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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 with...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Captain's Haven1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Garden
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    An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest located on White Pond. This true Cape cottage is ideal for a couple or a small family. It has a complete kitchen/ living area with a pull out sofa bed, one bedroom with 2 twin beds...
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    West Chatham, Chatham 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    This perfectly situated Chatham rental is welcoming to you and your four legged friends. Located close to Shore Road, you and your guests will enjoy the best of being near the ocean and close to Main Street. Stroll to town on sidewalks and enjoy the amazing shops and restaurants. Head to the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
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    2018 Rental Rate: $6825 per week, including the cleaning fee ~~ Off-Season:$5325 per week, including the cleaning fee ~~ Weekly rentals from mid-JUNE to mid-SEPT ~~ Lovely home in sought after Stage Neck area! This spacious home offers a private setting on just over an acre of land. It is about 2...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
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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 incredible views, a touch of opulence, room enough for 8, and is just a short drive from gorgeous ocean beaches...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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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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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
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    Experience 'Chatham Coastal Charm'. Popular Contemporary Cape Cod Vacation Rental home in Chatham with heated salt water gunite pool that is just a short walk to Hardings Beach (.3). Sleeps 10! Don't miss this 'fan favorite' Cape Cod Vacation Rental home in Chatham with heated pool that is very...
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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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    Pet friendly
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    Dog Friendly! Located in a prime in-town location. This Cape Cod Vacation Rental Cottage complex is just steps to the Mill Pond (a saltwater inlet of Nantucket Sound) in Chatham's Old Village and a few blocks to the Beautiful Lighthouse Beach. This desirable and newly renovated family compound...
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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 10 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
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    2018 Rental Rate ~~ FRIDAY TO FRIDAY: $13,600 per week, including the linens and cleaning fee Off-Season $7,600 per week, including the linens and cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This one of a kind secluded residence overlooking a stunning Chatham Seascape exudes timeless...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    2017 Rental Rate: $1225 per week including the cleaning fee ~~ Off-Season: $950 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Adorable one bedroom unit just steps to Lighthouse Beach! A quick walk to downtown Chatham for dinner, shopping and more, this charming condo...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Less than a mile from Chatham Village this 4 bedroom, 3 bathroom rental has all the comforts of home. The master bedroom with queen bed and a second bedroom with 2 twins are located on the 1st floor. The other two bedrooms and a bathroom are located on the second floor. Amenities include central...
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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 8 Quick View
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    Welcome to Cranberry View! Pet Friendly (dogs only please).  Relax in this 3 bedroom, 2 bath Cape Cod Vacation home in Chatham that is convenient to downtown Chatham and beaches. Privacy abounds just off Main Street and the home even overlooks a working Cranberry Bog! Window A/C units in Bedrooms...
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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 8 Quick View
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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. Calling all beach goers!! You...
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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 6 Quick View
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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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    South Chatham Cape Cod Vacation Rental (2400)1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    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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    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, 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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Roll out of bed and onto the shore of one of the most beautiful beaches on Cape Cod! Hardings Beach is miles of fun, family friendly, coastline and this beautiful classic turn of the century Chatham rental house is located less than 3 minutes walk to the sand! This charming turn of the century...
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    South Chatham, Chatham 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Welcome to Forest Beach Cottage. This Cape Cod Vacation home rental in Chatham is just yards out of the back door to Forest Beach. Central AC for those hot summer nights. You can smell the salt water from this ranch-style home with four bedrooms, two baths, and an outstanding family room. (Small...
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    South Chatham, Chatham 02659
    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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    Located on a quiet side street close to Pleasant Street Beach and Red River Beach this bright 3 bedroom, 2 bath home is sure to please. The open floor plan with wood floors throughout, updated kitchen and living area with cathedral ceiling flows through french doors into a large sun room with a...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pleasant Forest Shores cottages #3 : So. Chatham1 / 14
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
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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 - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    About this property
    Your perfect vacation starts here in this 2017 renovated 4-bedroom home close to Shore Rd and downtown Chatham. Easy walk to restaurants, shops, Oyster Pond, Chatham Bars Inn, Fishing Pier, playground, and A's ball field. Patio with grill, outdoor shower, huge lawn, half basketball court. Both a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, 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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    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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Escape to this 1801 Sea Captain's House with alluring old-world charm in Chatham for the ultimate Cape Cod getaway! With 5 bedrooms,4.5 bathrooms and accommodations for 10 this vacation rental house is the ideal size for families, friends, or couples traveling together. Whether you're seeking...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lovely, renovated and very clean. Two-full bath condo near Ridgevale Beach. No roads to cross to access the beach road. Full kitchen and dining; Enjoy the private patio area with weber grille overlooking lovely plantings and lawn area. air conditioning , comfortable furnishings, and child...
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    Chatham, Cape Cod 02633
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • Waterfront
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    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
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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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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    $2,000 01/01 - 06/08 $2,400 06/09 - 06/22 $3,000 06/23 - 07/20 $3,400 07/21 - 08/24 $3,000 08/25 - 08/31 $2,400 09/01 - 09/14 $2,000 09/15 - 12/31 This recently renovated and fully updated 4 bedroom, 2 bathroom Chatham vacation rental is located in Harbor Cove Association with private association...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate $7900 per week including the cleaning Off-Season: $5600 per week, including the cleaning fee Fabulous home with all the bells and whistles, with deeded access to Stage Harbor beach. Professionally decorated, this 4 bedroom home is full of new high-end furniture, fresh paint, and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Experience: Chatham Breeze. 4 bedroom, 3.5 bath Cape Cod Vacation Rental home tucked up off of Bridge Street, in Chatham. BONUS: Linens included IN SUMMER SEASON. Privately placed on just over a half acre of land in a peaceful setting, yet just a hop, skip and a jump away you can find Lighthouse...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Fabulous opportunity to rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28. Forest Street Beach on Nantucket Sound, a little piece of heaven, just 5/10th's of a mile, +/- down the street. This charming, upscale beach house has been beautifully updated...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    Beautiful Home in North Chatham! This light filled, spacious and comfortable home in North Chatham is a perfect spot for your Cape Cod vacation! Located on a large lot with a fantastic patio, you will enjoy outdoor living as well as the beautiful interior. Close to Cotchpinicut and Scatteree,...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Come Stay at: Good Times! Welcome to your Beach House! This Cape Cod Vacation rental home is located in Chatham in the Harding's Beach Hills (just .3 mile to Harding's Beach and .2 mile to The Buck's Creek Association dock and picnic area). Spacious 3+ Bedrooms with 2 extra private bonus rooms with...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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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 comfortably...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    This landmark property has the most remarkable views anywhere! After a day at the beach relax and take in one of the prettiest views on the Cape. Three bedrooms, bonus sleeping area, one full and two half baths and on a quiet cul-de-sac, at the very end of the road and sitting on just over an acre...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    Spend the summer on one of Chatham's most exclusive streets in this beautiful home. Located close to the beach, and to Main Street Chatham, the property at 61 Shore Road will please any discerning traveler. Graciously appointed with six bedroom and five full bathrooms, this home is well suited to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 13
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    Chatham  Cape Cod Waterfront Vacation Rental (6520)1 / 22
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Magnificent views of Bassing Harbor, Ryder's Cove and Pleasant Bay from this 4-bedroom, 3 bathroom waterfront home perched high on a bluff. This home boasts an expansive deck with plenty of outdoor seating for relaxing or dining alfresco and a spacious yard including a stairway leading down to the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Enjoy the Cape from this bright, beautiful townhouse on bustling Main Street in Chatham! This lovely multi-level townhouse is cozy and offers guests two bedrooms and two and a half baths. Two bedrooms, each with one queen sized bed, as well as a double sized sleep sofa in the living area...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cape Cod Pine Grove Cottage - 1/2 mile from beach!1 / 15
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    This immaculate two-bedroom/one-bath cottage sleeps five and is cozy and affordable. It's located one-half mile from Cockle Cove Beach on warm Nantucket Sound. Situated on a quiet cul de sac with a nearby childrens playground, this property is protected and cooled by pine trees and salty breezes....
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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