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Chatham House Rentals

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    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Step back in time in this beautiful 4 bedroom, 2 full bath traditional Cape beach house. There are panoramic views of Nantucket Sound from most rooms in the house as well as from the furnished deck. The private path and stairway leading to the priva DVD player, Wi-Fi, gas grill and an enclosed... View all property information
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    Chatham, Cape Cod 02659
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2016 Rental Rate: $2700 per week, with the cleaning fee~~~ Off-Season: $2200/wk, with the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Great family rental located on a quiet street in the Ridgevale Beach area of Chatham. Not far from the beach, it offers a spacious back deck overlooking... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2016 Rental Rate: $1925 per week, including the cleaning fee *10 Day Special Aug 27-Sept 6 $1925!* ~~NO OFF SEASON~~ Wonderful, well-maintained home only a few minutes to Hardings Beach by car, without fighting Route 28 traffic; only 500 yards to the town landing on Oyster River (see photo on... View all property information
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    Chatham, Cape Cod 02633
    1 / 10
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    2016 Rental Rate: $2275 per week, including the cleaning fee Off-Season (June only): $1675/wk including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Located in a quiet neighborhood, 1/4 mile from Forest Beach. Charming home with a comfortable living room. Bright & spacious sun room... View all property information
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    South Chatham, Chatham 02659
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    2016 Rental Rates: $5800 per week, including cleaning fee Off-Season: $4100/wk, including the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT Location Location Location! This wonderful, family rental is a short walk or easy bike ride into downtown Chatham and offers swimming/sunbathing... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This Chatham rental home has 3 bedrooms and 1.5 baths. It's situated in a private setting, abutting conservation and convenient to both downtown Chatham and beaches. This property is only 1/2 mile to White Pond, a large fresh water pond which is great for fishing, swimming or paddle boarding.... View all property information
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    Chatham, Cape Cod 02633
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    2 of 5 stars (1) Poor
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Pet Friendly!! High atop Sears Point in Chatham sits a Classic, Quintessential, New England Bluff house from yesteryear overlooking the sparkling, blue sea. Peak Summer Weekly Rates: last week of June until the first week in September: $6000 $6,500/week. This spot is a boater's paradise! From... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    2016 Rental Rate: $1525 per week including the cleaning fee ~~ Off-Season: $925 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Light and bright two bedroom condo near Lighthouse Beach. New carpeting, new furniture, and new hardwood floors really brighten up the decor.... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    2016 Rental Rate ~~ FRIDAY TO FRIDAY: $14,600 per week, including the linens and cleaning fee Off season $9600 per week including the cleaning and linens Weekly rentals from mid-JUNE to mid-SEPT This one of a kind secluded residence overlooking a stunning Chatham Seascape exudes timeless elegance... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Lovely renovated home with central air just steps away from Lighthouse Beach. Lovely renovated home just 5 doors down from beautiful Lighthouse Beach- you don t have to worry about parking! This home features many upgrades including central air conditioning and lovely, comfortable living spaces. So... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2016 Rental Rate: $3275 per week, including the cleaning fee Off Season: $2275 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will be sure to enjoy your time in the idyllic town of Chatham, MA in Cape Cod. This home is 1/2 mile from the quaint town center and... View all property information
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    Chatham, Cape Cod 02633
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    5 of 5 stars (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Pet Friendly! Relax and enjoy this Chatham, Cape Cod Vacation Rental Home offering 6 bedroom 6.5 bathrooms. Peak Summer Weekly Rates: last week of June until the first week in September: $16,525/week. This luxury home is pet friendly with a private pool, central a/c, linens, wifi and more. In... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    255 Tanglewood Drive CHATHAM This Chatham home is conveniently located within a short drive to many salt water beaches and fresh water ponds. The Chatham Bike Path is less than 1 mile away. Home is also convenient to down town Chatham and Harwich Port offering many shopping and restaurant choices.... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 13
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2016 Rental Rates: $2475 per week, including the cleaning fee ~~ Off-Season: $1375 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... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    5 of 5 stars (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Waterfront
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    • Hot Tub
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    About this property
    Paradise found on the shores of Eastward Point in Chatham! Luxury at its finest will surround you at every turn in this renovated, contemporary Cape Cod Vacation home offering central air and wireless internet. Peak Summer Weekly Rates: last week of June until the first week in September:... View all property information
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    Chatham, Cape Cod 02633
    1 / 27
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Luxury Chatham Home, Water Views, Private Beach Peak Summer Weekly Rates: $5,650-$6,050The home is set in a private neighborhood with tranquil views of Pleasant Bay and a one minute walk to a private association beach. Inside, the home is clean and modern with an open floor plan, 2 flat screen... View all property information
    Location Information
    North Chatham, Chatham 02650
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    2016 Rental Rate: $4270 per week including the cleaning fee. This is a FRIDAY TO FRIDAY RENTAL only. Off-Season: $3270 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming Cape-style home on Main Street in Chatham's Old Village. Located just blocks from the shops... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 18
    6 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Waterfront cottage on Nantucket Sound. Enjoy the spectacular location and panoramic waterviews from this 6 bedroom, 2 bath Chatham rental cottage situated right on Cockle Cove Beach on Nantucket Sound. This is one of very few cottages where you can step out your door and take only a few steps to... View all property information
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    Chatham, Cape Cod 02659
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    2016 Rental Rate: $2425 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT No off-season rentals 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... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spend your Cape Cod vacation in this well cared for 4 bedroom, 2 bathroom South Chatham rental home only 2/10ths of a mile to Pleasant Street Beach on Nantucket Sound. Forest Beach is only 3/10ths of a mile away as well. The screened in porch overlooking the woods is peaceful and spacious. Perfect... View all property information
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    Chatham, Cape Cod 02659
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    155 LIME HILL ROAD CHATHAM Large and lovely 4 bedroom home built to a very high standard. Just a short distance to Chatham Village and all it has to offer. Beautiful yard and grounds, this home is a joyful place in the summertime. Offering 4 comfortable bedrooms, a generous kitchen and central... View all property information
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    Chatham, Cape Cod 02633
    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2016 Rental Rate: $3000 per week, including the cleaning fee ~~ Off Season: $1700 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... View all property information
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    Chatham, Cape Cod 02633
    1 / 1
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    2016 Rental Rate: $5000 including cleaning fee FRIDAY TO FRIDAY ~~ Off Season: $3700 including the cleaning fee FRIDAY TO FRIDAY RENTAL Beautiful, new home centrally located in Chatham with upscale and lavish furnishings throughout. Simple elegance defines the home with Custom Hardwood, stone and... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Situated on a cul-de-sac just 3/10ths of a mile to Pleasant Street Beach and 4/10ths to Forest Beach, you'll enjoy this comfortable 4 bedroom, 2 bath home. Amenities include Wi-Fi, cable TV (includes sports and weather), DVD player, window AC units in the living room, dining room and in each of the... View all property information
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    Chatham, Cape Cod 02659
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2016 Rental Rate: $2175 per week, including the cleaning fee~~ Off-Season Rate: $1675 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Cozy saltbox located only a couple of blocks from Chatham's popular Harding's Beach. The first floor has a spacious bedroom with a... View all property information
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    Chatham, Cape Cod 02633
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    2016 Rental Rate ~ $3700 per week, including the cleaning fee Off Season, $2900 per week, including the cleaning fee Gorgeous, upscale rental located in the heart of downtown Chatham. Enjoy your vacation from this penthouse condominium, overlooking the sights & sounds of Main Street. The great room... View all property information
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    Chatham, Cape Cod 02633
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    South Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This Cape Cod Vacation home Rental in Chatham is just yards out the back yard to Forest Road Beach. Peak Summer Weekly Rates: last week of June until the first week in September: $2,850/week. Central A/C for those hot summer nights. You can smell the salt water from this ranch style home with four... View all property information
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    South Chatham, Chatham 02659
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2016 Rental Rate: $4250 per week, including the cleaning fee Off-Season: $3250 per week, including the cleaning fee Fabulous three bedroom home in a great central location and steps to swimming in the fresh waters of Schoolhouse Pond! This spacious home is filled light and bright furnishings, and... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    About this property
    338 Seapine Road CHATHAM, ID# 104736 Waterfront 3 bedroom home overlooking Bassing Harbor and Fox Hill with the outer barrier beach beyond. Located on a cul de sac in a highly desirable neighborhood, the home is a classic cape in style. Water access for kayaking in Pleasant Bay and beyond. This... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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... View all property information
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    Chatham, Cape Cod 02659
    1 / 37
    9 Bedrooms, 5 Bathrooms, Sleeps 20 | Quick View
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    • Outdoor Dining Area
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    About this property
    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! Peak Summer Weekly Rates: last week of June until the first week in September: $7,500... View all property information
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    Chatham, Cape Cod 02633
    1 / 31
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    About this property
    This Cape Cod Vacation Rental Home is located on a dead end street in a central Chatham location close to town and offering Central AC. Peak Summer Weekly Rates: last week of June until the first week in September: $3000 - $3,500/week. Walk to Oyster Pond, also into the downtown Village of Chatham... View all property information
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    Chatham, Cape Cod 02633
    1 / 5
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
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    About this property
    2016 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... View all property information
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    Chatham, Cape Cod 02633
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Grill
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    2016 FRIDAY TO FRIDAY Rental: In Season $3950 per week with the cleaning fee ~~~ Off Season $2650 per week with the cleaning fee included Weekly rentals from mid-JUNE to mid-SEPT You cannot beat the fabulous views from the decks of this sprawling Cape Cod retreat! There is a lot of space for two... View all property information
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    Chatham, Cape Cod 02633
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    You'll have beautiful views of Nantucket Sound from this 2 bedroom, 1.5 bath traditional Chatham vacation rental only 4/10ths of a mile to Red River Beach and 6/10ths of a mile to Pleasant Street Beach. This home has a finished basement with a large flatscreen TV with surround sound, pool table,... View all property information
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    Chatham, Cape Cod 02659
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    2016 Rental Rate: $2575 per week, with the cleaning fee~~~~Off-Season: $1775 per week, with the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT FRIDAY TO FRIDAY RENTALS DURING SUMMER MONTHS Updated, light & bright home located about 1/2 mile from downtown Chatham & Oyster Pond. New kitchen... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • Child-friendly
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    • Elder access
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    About this property
    2016 Rental Rate: $3275 per week including the cleaning fee Off-Season: $1875 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Walk to town in minutes from this recently updated ranch on Highland Avenue! Light and bright with new furnishings throughout, this adorable... View all property information
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    Chatham, Cape Cod 02633
    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Parking
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    About this property
    Why pay the new Homeaway/VRBO surcharge? Book with confidence and save when you book direct with Pretty Picky. Chatham Village Charm Next to Chatham Light Peak summer weekly rate: $6,200 This 5 bedroom home offers impressive views of the Atlantic Ocean and a short walk across the street to... View all property information
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    Chatham, Cape Cod 02633
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Spend your vacation in this newer 2+ bedroom, 2.5 bath Chatham rental home situated on a lovely country lane only 3/10ths of a mile to Pleasant Street Beach on Nantucket Sound. The master bedroom with queen bed is located on the first floor. The second floor bedroom has a queen and a twin bed and... View all property information
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    Chatham, Cape Cod 02659
    1 / 1
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
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    About this property
    2016 Rental Rate: $3900 per week, including the cleaning fee No Off-Season Weekly rentals from mid-JUNE to mid-SEPT A fantastic, family rental steps from Main Street and Veterans Field. Completely updated throughout and located on a quiet dead end street, just off the beaten path. Large Master on... View all property information
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    Chatham, Cape Cod 02633
    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    2016 Rental Rate: $1775 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Here is a great deal!! Clean and spacious 3 bedroom, home that sleeps 8 people comfortably, with plenty of room to spread out. This centrally located home is convenient to the bike trail, South... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Grill
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    • Patio
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    2016 Rental Rate: $3975 per week including the cleaning fee No Off Season Classic Cape walking distance to Harding's Beach; the entire family can handle the quick walk down to popular, kid-friendly Hardings Beach. This home has six air conditioning units as well as high speed internet. A giant... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    $13,200 /week Peak Season (July 2 - September 3) $9,100/wk for the weeks of (6/25 and 9/3) $7,800/week Shoulder Season (6/18 and 9/10) $6,800/week Shoulder Season (6/11 and 9/17) $6,100/wk (before 6/11 and After 9/24) Spend your Chatham vacation in this beautiful brand new 4 bedroom 4.5 bath home... View all property information
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    Chatham, Cape Cod 02659
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Child-friendly
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    About this property
    Spend your vacation in this newer 4 bedroom, 3.5 bath Chatham rental home situated 3/10ths of a mile to Pleasant Street beach on Nantucket Sound. This home boasts nearly every possible amenity including central AC, washer, dryer, dishwasher, cable TV (includes sports and weather), DVD, Wi-Fi,... View all property information
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    Chatham, Cape Cod 02659
    1 / 6
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Air Conditioning
    • Washer
    • Internet Access
    • Grill
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    2016 Rental Rate: $3375 per week including the cleaning fee and linens ~~ Off-Season: $2575 per week including the cleaning fee and linens Weekly rentals from mid-JUNE to mid-SEPT Classic, old-school cape cottage located just steps to downtown Chatham, Chatham Bars Inn, Seaside Links, and Claflin... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
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    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    2016 Rental Rate: $1650 including cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Comfortable cottage located in the Harding Beach area. The perfect spot for your family's summer vacation! Relax on the screened in porch or take a quick walk down to Harding Beach! A great, affordable rental in... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Patio
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    • Air Conditioning
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    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    2016 Rental Rate: Pre-season (May 28-June 18) $1,200 per week ~~~IN SEASON: $1800 per week (June 18-Sept 10) ~~~Post-season (Sept 10-Oct 15th) $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... View all property information
    Location Information
    Chatham, Cape Cod 02633