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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.
    390 Matching Rentals in ChathamView all 417 rentals
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Charming cape-style pet friendly home close to all that the village has to offer. PET FRIENDLY charming cape-style home close to all that the village has to offer. Close to town, Oyster Pond, Chatham Anglers games, golf, and tennis courts. Enclosed outdoor shower and patio with outdoor dining- 4...
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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 (3631)1 / 17
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Situated at the end of a cul-de-sac in a wonderful neighborhood this Chatham home has a very private backyard which abuts conservation land. This 4 bedroom, 2 bath home is also just a half-mile from Nantucket Sound Beaches. Amenities include central AC, washer, dryer, dishwasher, cable TV (includes...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Located outside of downtown Chatham sits this charming four bedroom home, known as Stones Throw. This property features great amenities such as central air conditioning, high speed wireless internet, and flat screen TVs in every bedroom. Enjoy an outdoor dinner in your central courtyard accessed...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This renovated 3 bedroom, 2 bathroom property in the Ridgevale Beach area is well equipped to make your vacation stay comfortable. The home features gleaming hardwood floors on the first floor, new carpeting on the second floor, updated bathrooms and a fully equipped kitchen. New for 2018 is an...
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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 6 Quick View
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    2018 Rental Rate: $3575 per week including the cleaning fee. ~~ Off-season: $2575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming home right on Seaview Street - a short walk to downtown Chatham, or Chatham Bars Inn! This home has lovely furnishings throughout,...
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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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    Spectacular Waterfront Townhome - Oyster Pond #321 / 14
    (6)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Incredible two bedroom, three full bathroom end-unit with gorgeous direct water views of Oyster Pond. Beautifully decorated with charming interior decor....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Large home sleeps 12 in Chatham Wonderful vacation home on one acre of land. Very private backyard in Charming Chatham. Boasts all of the amenities, newly rennovated kitchen and bathrooms, air conditioning units in all bedrooms and living areas. Close to town, School House Lake, Beaches, and Cape...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2018 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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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick 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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    6 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    209 Champlain Rd Chatham MA DOG FRIENDLY Great, rambling home with an old-Cape Cod feel located on the 'loop' just around the bend from Stage Harbor. Wonderful area to enjoy while here on the Cape! A tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Comfortable 3 bedroom, 2 bath quiet summer retreat only a half mile to downtown Chatham! Offering Central AC & Wifi with over 1600 sq. ft. of finished living space, 3 bedrooms, 2 full bathrooms, and a large den there is plenty of space for you to relax in with the entire family. Welcome to The...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Tucked in the private Cannon Hill setting, this enchanting 4 bedroom, 3 full and 1 half bathroom home with a large 40 x 20 heated salt-water pool offers tons of comfort and is perfect for your summer getaway. Just a short 3 minute stroll away, on the calm waters of Pleasant Bay, a private...
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    Chatham, Cape Cod 02650
    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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    241 Training Field Road PET FRIENDLY Charming and updated 3 bedroom air conditioned ranch style home, just 1 mile from beautiful Pleasant Bay at Jacknife Point Beach. $1900 per week in season * $160 Cleaning Fee * $100 Handling Fee * $55 Damage Insurance OR $500 Security Deposit Please contact...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    30 Seabeach Road Chatham Cape Cod - The Bluff House1 / 36
    (4)Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Come Stay at: The Bluff House! Dog Friendly!! High atop Sears Point in Chatham sits a Classic, Quintessential, New England Bluff house from yesteryear overlooking the sparkling, blue sea. This spot is a boater's paradise! From kayaking to boating enthusiasts, there is a mooring available for your...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    Chatham Cape Cod Vacation Rental (10327)1 / 12
    (1)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Enjoy this classic 3 bedroom, 1 full bath Cape beach cottage only 3/10ths of a mile to popular Ridgevale Beach. Amenities include washer, dryer, dishwasher, two window AC units (one in the Queen bedroom and one in the bedroom with 2 Twins), cable TV, DVD player, Wi-Fi, furnished deck, both gas and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome to The Rosa Rugosa! Walk to Hardings Beach- Central air - private! Ranch-style home with Central air-comfortable, easy living all on one floor! 3 Bedrooms, 2 baths, sleeps 6 with central air, WiFi, and sunroom. Beautiful gardens, patio, yard, and an easy walk to Harding's Beach! Quiet side...
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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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    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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    WATERFRONT on Lover's Lake - CM03751 / 18
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Waterfront on Lovers Lake, 1 AC This lovely 3 bedroom, 2 bath ranch features a private, sandy beach right on Lovers Lake (one of Cape Cod's beautiful, glacier-formed kettle ponds); ideal for swimming, or bring your kayak and enjoy the serenity. This property is located down a quiet cul-de-sac in...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2018 Rental Rate: $1325 per week, including the cleaning fee ~~~ Off-Season: $1075 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming cottage in the woods and only 2 minutes to Oyster River Public Boat Landing. Small screened-in porch attached. A great vacation...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Captains Row E Chatham Cape Cod - Captain's Row1 / 26
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Welcome to Captain's Row! Enjoy easy resort style living in this newer Cape Cod Vacation Rental home in Chatham. This home is in its own residential sub division and is close to beaches, restaurants, downtown and includes a community pool & tennis court (Only 130 steps from your door!). Also...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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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, 3 Bathrooms, Sleeps 9 Quick View
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    Welcome to Summer Oasis! Newer Custom Cape Cod Vacation Rental home that is walk to beach in Chatham sleeping 9. A walk for most to Cockle Cove Beach at the end of the street on the Nantucket Sound (0.6 mile)! Central air, WiFi, a screened in porch, 3 spacious bedrooms, and open concept living will...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    4BR South Chatham House in Cape Cod!1 / 25
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Begin your Cape Cod adventure by staying in this beautiful 4-bedroom, 3-bathroom saltbox home. Surrounded by natural beauty and close to everything the Cape has to offer, this home is a perfect choice for a group of friends traveling together or a family getaway. Your whole group will love calling...
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    South Chatham, Chatham 02659
    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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    #604 The Hideaway: Less than a mile to one of the best beaches in Chatham! Feel the warm sand between your toes at Cockle Cove beach, just .8 mile walk/bike ride. Downtown Chatham just minutes away. The Hideaway lives up to its name with being tucked away at the end of a private road, completely...
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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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    On the Water! With Central Air and Wireless Internet-Pet Friendly too. SPECIAL: Book the last great week of the Season in 2018: SUNDAY- SUNDAY August 26-Sept 2 CALL IN SPECIAL ONLY: $6000! A savings of $500!!! Pet friendly for Dogs only-ask your rental specialist for details. This Cape Cod Vacation...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rates: ~~~Pre-season (May 13-June 16) $1,200 per week ~~~IN SEASON: $1800 per week (June 17-Sept 9) ~~~Post-season (Sept 9-Oct 14th) $1,200 per week Off-season (subject to Owner's prior approval) $800 week $175 MANDATORY cleaning fee per lease Weekly rentals from mid-JUNE to mid-SEPT...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chatham Cape Cod Vacation Rental (9068)1 / 17
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Enjoy this 3 bedroom, 1.5 bathroom Chatham vacation home in the Harding's Hills neighborhood only 1/2 mile from popular Harding's Beach. There is a bonus 'Florida room' with full-size futon for sleeping or enjoying the afternoon sun. The backyard patio has a great dining table with umbrella, a gas...
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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 7 Quick View
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    2018 Rental Rate: $2450 per week including the cleaning fee No Off-Season Comfortable and airy post & beam home located in a quiet neighborhood near Harding's Beach. Tons of windows and skylights throughout bring in the sunlight! The eat-in kitchen overlooks the backyard gardens and walks out to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    169 Lime Hill Road CHATHAM This magnificent and well-appointed home is the epitome of luxury living with added Cape Cod style. Conveniently located less than 3/4 of a mile from Chatham Village, you also have deeded rights to a path to Oyster Pond.. Every amenity is provided, from central air to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 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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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    195 Cedar Street Chatham - ID# 106000 Location, location, location! Only a half mile to the beach at Oyster Pond and 3/4 mile to the Village of Chatham. Located on the Chatham Loop, this is a wonderful newly renovated home including a fabulous new kitchen with sunny breakfast nook. Living room,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    This 4 bedroom, 2.5 bathroom home in South Chatham has plenty of space inside and out. There is a sunken dining room off the main living room that opens to a furnished patio with gas grill. A second living space on the lower level has a TV, foosball table, half-bath, wet-bar area, two sleep-sofas...
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    South Chatham, Chatham 02695
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    2017 Rental Rates ~~ In Season, $2900 per week, including the cleaning fee Off Season, $2200, including the cleaning fee Beautiful home built in 2006 with an airy open floor plan and tons of living space throughout. Great central location, close to all the shops and restaurants Chatham has to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Outdoor Dining Area
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    Wouldn't you like to spend some time at this adorable updated Cape Cod Vacation Rental cottage in Chatham? It is in a convenient location with a path at the end of the road to Forest Beach. It is also just a short walk to Pleasant Road Beach. The bike trail is just off Route 28 on the corner of...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Dog Friendly! Located in a prime in-town location! This Cape Cod Vacation Rental Cottage complex offers deeded access to the Mill Pond (a saltwater inlet of Nantucket Sound) and is just a few blocks to the beautiful Lighthouse Beach in Chatham's Old Village. This desirable and newly renovated...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Vacation Spot Right up the Road from Pleasant Street Beach in South Chatham! Well appointed and comfortable, this home is convenient to all the area has to offer. Enjoy grilling on the deck in the private backyard after a day enjoying summer on Cape Cod! Four bedrooms and 2 1/2 bathrooms...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    255 Tanglewood Drive CHATHAM Just a short drive to many salt water beaches and fresh water ponds, as well as both downtown Chatham and Harwich Port, this house is convenient indeed! The backyard is fully enclosed and offers a great place to relax and grill after enjoying all the many things this...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Chatham Cape Cod Vacation Rental (7102)1 / 15
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Spend your Cape Cod vacation in this 3 bedroom, 2 bathroom rental home close to the downtown area, fish pier, ball field, playground and bakeries. Amenities include central AC on the 1st floor and window units in all of the bedrooms, washer, dryer, dishwasher, Wi-Fi, cable TV (includes sports and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rates: $2600 including the cleaning fee. Off-Season: $1600 including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Wonderful, light and bright summer home located just steps from Taylor's Pond, the Eel River and the warm waters of the Nantucket Sound. Even better, there is a...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $6450 per week, including the cleaning fee This recently renovated antique farmhouse is filled with upscale furnishings and is practically in the center of town! Located on large lot, it offers a wonderful mixture of new and old. There is one bedroom on the first floor with a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    2018 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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Location, location, location. Enjoy this classic 2 bedroom, 1 full bath Cape beach cottage less than 2/10ths of a mile to popular Ridgevale Beach. Amenities include window AC units in the queen bedroom as well as the kitchen/living room area, washer, dryer, dishwasher, cable TV (including sports...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2018 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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