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Chatham House Rentals

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    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    Welcome to: Cape Cranberry! Quintessential Cape Cod Vacation Rental Cottage in Chatham on the way to Cockle Cove Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $1,400/week. Enjoy this Cape Cod beach cottage with casual coastal decor. A/C units in living area... View all property information
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    Chatham, Cape Cod 02633
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    North Chatham
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $1725 per week, including the cleaning fee ~~ Off Season: $1125 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Recently remodeled cottage with central air is close to shopping and restaurants in downtown Chatham, baseball games at Veteran's Field,... View all property information
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    North Chatham, Chatham 02650
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Come stay at: Seashell Beach Cottage! Beach front vacation rental cottage in Chatham! Peak Summer Weekly Rates:  last week of June until the first week in September: $2,800/week. Stay at this 2 bedroom cottage located right on the beach in Chatham, the best of Cape Cod. Beautiful views! Perfect for... View all property information
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    Chatham, Cape Cod 02633
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    South Chatham
    Studio, 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... View all property information
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    South Chatham, Chatham 02659
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    North Chatham
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Come stay at: Misty Meadow! Completely renovated vacation condo on Cape Cod in North Chatham. Enjoy this lovely condo with all amenities including Central A/C mini splits, wifi, and everything new. Peak Summer Weekly Rates:  last week of June until the first week in September: $1,275/week.... View all property information
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    North Chatham, Chatham 02650
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    Experience: Chatham Breeze. Luxury 4 bedroom, 3.5 bath Cape Cod Vacation Rental home tucked up off of Bridge Street, in Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $6,400/week Privately placed on just over a half acre of land in a peaceful setting, yet... View all property information
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    Chatham, Cape Cod 02633
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    North Chatham
    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... View all property information
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    North Chatham, Chatham 02650
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    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate: $6250 per week, including the cleaning fee Off-Season $4450 per week, including the cleaning fee The perfect place for a most memorable and rewarding vacation. New owners of this original Morris Island home have brought in all new furnishings and bed sets. The spacious open floor... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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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! Peak Summer Weekly Rates:  last week of June until the first week in September: $7,000/week. Don't miss... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 3 Bathrooms, Sleeps 7 | Quick View
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    Come Stay at: Chatterbox! Location! Location! Location! Luxury Chatham Vacation Rental home with 3 bedroom, 3.5 bath in the heart of Chatham and sleeps 7. Peak Summer Weekly Rates:  last week of June until the first week in September: $4,000 - $4,200/week. Whether you enjoy cocktails on the... View all property information
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    Chatham, Cape Cod 02633
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    5 of 5 bubbles (1) Excellent
    Studio, 7 Bathrooms, Sleeps 16 | Quick View
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    Come stay at: Sand Simeon. 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,... View all property information
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    Chatham, Cape Cod 02633
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    5 of 5 bubbles (2) Excellent
    South Chatham
    9 Bedrooms, 4 Bathrooms, Sleeps 20 | Quick View
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    Southwesterly ocean breezes flow over this HISTORIC family estate built in the 1930?s by Mr. & Mrs. John Peale Bishop, a classmate and best friends at Princeton of F. Scott Fitzgerald and himself a famous writer and poet. The Gatsby sits on 1.3 acres in Chatham overlooking Nantucket Sound.... View all property information
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    South Chatham, Chatham 02659
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    South Chatham
    Studio, 3 Bathrooms, Sleeps 9 | Quick View
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    Newer Custom Cape Cod Vacation Rental home that is walk to beach in Chatham sleeping 9. Peak Summer Weekly Rates:  (last week of June until the first week in September) $3,400 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... View all property information
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    South Chatham, Chatham 02659
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    South Chatham
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    2017 Rental Rate: $2275 per week, including the cleaning Off season, $1575 per week, including the cleaning Wonderful, clean, and comfortable home located in the quaint village of South Chatham. Enjoy your afternoons at the beach and your evenings in the bug free screened porch ! Within a quick... View all property information
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    South Chatham, Chatham 02659
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    4 of 5 bubbles (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Swim, fish, bike or just plain relax at this comfortable retreat in Chatham. In a quiet, wooded setting, cooled by the breezes from the pond, window AC's and ceiling fans, the home's open floor plan is well suited for gathering. The first floor of this home includes the living room, dining room,... View all property information
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    Chatham, Cape Cod 02633
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    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to The Little Caper. This updated 4 bedroom, 2 bath vacation rental home in Chatham is well maintained and a great spot for making family memories. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,800/week and just $1,900 in Sept and October!! Just under a... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 3 Bathrooms, Sleeps 9 | Quick View
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    Chatham Village Charm Next to Chatham Light Peak summer weekly rate: $4,900 - $5,900 (Rents Saturday to Saturday during peak season) This 5 bedroom home offers impressive views of the Atlantic Ocean and a short walk across the street to Lighthouse Beach.This updated home has been renovated with the... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Pet Friendly! Located in a prime in-town location. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,300/week. 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... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    Classic Chatham Charm -- Walk to Beach & Town! (Linens included) Peak Summer Weekly Rates: $5,900 - $6,750 (Pets Considered) (Rents Saturday to Saturday during peak season) Located in a premier Chatham Village location, this classic antique home has everything to experience an idyllic Chatham... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Pet Friendly! Located in a prime in-town location. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,875-$3,975/week. 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... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    2017 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 Updated, light & bright home located about 1/2 mile from downtown Chatham & Oyster Pond. New kitchen and furnishings throughout, as well as a newly... View all property information
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    Chatham, Cape Cod 02633
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    2017 Rental Rate: $3275 per week, including the cleaning fee Off Season: $1475 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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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate ~ $1650 per week, including the cleaning fee Off-Season: $1200 per week, including the cleaning fee Comfortable summer rental home in a great central location! This three-bedroom ranch sits on a quiet street located in West Chatham. Just a quick drive in one direction to spend the... View all property information
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    Chatham, Cape Cod 02633
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    North Chatham
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate: $2800 per week including the cleaning fee ***FRIDAY TO FRIDAY RENTAL*** ~~~ Off-Season: $2200 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming, antique home located in North Chatham with a pretty, private yard and distant views of the ocean... View all property information
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    North Chatham, Chatham 02650
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    This 3 bedroom cottage is the perfect location for your family stay in Chatham. The 3 bedrooms have one king room with a spacious en suite bathroom with Jacuzzi, and the other two with a queen sized bed in each. There are 2 sleeper sofas, one in the living room and the other in the family room. The... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    190 Countryside Drive - ID# 104736. Lovely 4 bedroom home in Chatham Charming 4 bedroom home in a peaceful area with a lovely fenced in yard. Just a short drive to Jackknife Cove beach on Pleasant Bay and a short distance to Monomoy River for kayaking and canoeing. School Houe Pond is a half mile... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    Location! Location! Location! This Cape Cod Vacation Rental Home named The Bottle Shop is located in the Old Village of Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,900 - $4,200/week. This home has been lovingly restored to keep the Cape Cod... View all property information
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    Chatham, Cape Cod 02633
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    North Chatham
    Studio, 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 mile to Chatham Lighthouse Beach and convenient to Scatteree Beach and the Cow Yard Landing! Approx. 2 miles to Main St., Chatham for shopping,... View all property information
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    North Chatham, Chatham 02650
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    Studio, 4 Bathrooms, Sleeps 11 | Quick View
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    2017 Rental Rate: $9350 per week, including the cleaning fee Call about Off-Season! The entire family will enjoy this gorgeous, newly built 4+ BR home with a private association path down to Ridgevale Beach! The beach is close, there is a path across the street that takes you to a bridge to the... View all property information
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    Chatham, Cape Cod 02633
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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.... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    ID #LAKE110 Lake front vacation home on Lovers Lake in Chatham in the Great Hill Neighborhood. [~]Heron Haven is a peaceful, spacious home in a beautiful lake front setting with many sought after features. This home sleeps 10 guests and boasts Central A/C and 4 living areas to spread out and... View all property information
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    Chatham, Cape Cod 2633
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Come stay at: The Cozy Beach Cottage! Chatham Vacation Rental Cottage at the beach! Peak Summer Weekly Rates:  last week of June until the first week in September: $2,000/week. Get away to this 1 bedroom cozy cottage located right at the beach in Chatham, the best of Cape Cod-Sleeps 4. Perfect for... View all property information
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    Chatham, Cape Cod 02633
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    South Chatham
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    #602 - Port View Home:  Nantucket sound awaits you in this sweetie beach house. Pull in the driveway, look to the left ... All you see is OCEAN. Magnificent Nantucket Sound with white sandy beach just waiting on you to put down the beach blanket and take a dip! Port view home offers great living... View all property information
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    South Chatham, Chatham 02659
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    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    WATERFRONT! Come stay at: Milhaven, This Cape Cod Vacation Rental is located in Chatham's Old Village and is right on Mill Pond. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,500 - $3,900/week. The Old Village is popular for its historic nature and architectural... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $1775 per week with the cleaning fee ~~ Off Season Rate: $1050 per week with the cleaning fee. Weekly rentals from mid-JUNE to mid-SEPT This three bedroom home is a stones throw from Chatham's bike trail, so you can ride from your home all over the Cape. The Regional Middle School... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 8
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rates ~ In Season, $1125 including cleaning fee No Off-Season Clean rental home located just 1/2 mile to Hardings Beach or Oyster River Boatyard. Fresh paint and furnishings throughout make this small yet comfortable rental a great buy! Good size living room with high ceilings make it... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 12
    5 of 5 bubbles (4) Excellent
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    This adorable, updated and meticulously maintained 2 bedroom, 1 bathroom quintessential Chatham vacation cottage has views of Nantucket Sound. This rental is only 2/10ths of a mile to Forest Beach and Pleasant Street Beach. (The rental does not included access to the beach shown in the photos which... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 8
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rate ~~ FRIDAY TO FRIDAY: $14,600 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 elegance and charm. Set within a spectacular landscape of 3.7 acres,... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 21
    5 of 5 bubbles (1) Excellent
    South Chatham
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    Great views of Nantucket Sound from this 3 bedroom, 2.5 bathroom Chatham cottage. This is a newer house with multiple furnished decks and balconies as well as a covered porch and is just a stones throw to a semi-private beach on Nantucket Sound. The master bedroom is detached from the main house,... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 13
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rate: $2175 including the cleaning fee Off-Season: $1575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Lovely home, on 1/2 acre wooded lot, only 1/2 mile to the warm waters of kid-friendly Ridgevale Beach! This comfy, spacious home features high speed... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 26
    North Chatham
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Completely renovated condo in North Chatham. Enjoy this lovely condo with all amenities including Central AC mini split, WiFi, and new furnishings. Sleeps 4. Read on to learn more about our Chatham Mass Vacation Rentals Peak Summer Weekly Rates:  last week of June until the first week in September:... View all property information
    Location Information
    North Chatham, Chatham 02650
    1 / 15
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • ?
    About this property
    2017 Rental Rate: $3225 per week, including cleaning fee No Off Season Beautiful, clean beach home located a quick half mile to Chatham's Ridgevale Beach. Plenty of space to spread out with the open floor plan, as well as the newly finished walk out basement. Huge, grassy back yard...perfect for... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 23
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Wi-Fi
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    • Satellite TV
    • Porch
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    On the Water! With Central Air and Wireless Internet-Pet Friendly too. Peak Summer Weekly Rates:  last week of June until the first week in September: $6,500/week Pet friendly for Dogs only-ask your rental specialist for details. This Cape Cod Vacation Rental home in North Chatham has... View all property information
    Location Information
    Chatham, Cape Cod 02650
    1 / 19
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Pet Friendly! Located in a prime in-town location. Peak Summer Weekly Rates:  last week of June until the first week in September:$2,000/week. 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... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 10
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Washer
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    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rate: $4225 per week, including the cleaning fee ~~~Off Season $3225 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will LOVE this beautiful home located in the Bailey's Path neighborhood, a lovely year round residential complex. The house is filled... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 11
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    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... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 12
    South Chatham
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    • Grill
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    • Patio
    • Washer
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    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rate: In Season, $3175 per week, including the cleaning fee No Off-Season Weekly rentals from mid-JUNE to mid-SEPT Recently renovated three bedroom home with beautiful views of Red River Marsh and Nantucket Sound! Filled with new furnishings and appliances, this spacious home offers... View all property information
    Location Information
    South Chatham, Chatham 02659