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House Rentals in Chatham, MA

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    Travellers to Chatham are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 22
    5 of 5 stars (11) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Private, Family Ranch Style Riverbay home in Chatham for your Cape Cod Vacation located on a peaceful residential dead end road. Peak Summer Weekly Rates: last week of June until the first week in September: $1600-$1,800/week As you enter the through the front door you will find comfortable seating... View all property information
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    Chatham, Cape Cod 02633
    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    Short Drive to Everything! Our cape home offers lots of space for your family. 3/4 mile to Pleasant Bay Beach, 1 minute walk to Ryder’s Cove boat yard, few minutes walk to tennis courts and Cape Cod bike trail. 5 minutes drive to town center. Close to playground and baseball field - home of the... View all property information
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    Chatham, Cape Cod 02633
    1 / 41
    5 of 5 stars (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Welcome to the Whydah Figawai - a privately-owned five bed room vacation home in exclusive North Chatham, just a few steps away from the private beach on Pleasant Bay. This traditional Cape Cod home is located in a serene setting and offers the perfect combination of quiet and accessibility for... View all property information
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    Chatham, Cape Cod 02650
    1 / 15
    5 of 5 stars (6) Excellent
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    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.... View all property information
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    South Chatham, Chatham 02659
    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    WATERFRONT! 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: $3,900/week. The Old Village is popular for its historic nature and architectural beauty. Witness beautiful sunset... View all property information
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    Chatham, Cape Cod 02633
    1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    Renovated Sea Captain's Home by Ryder's Cove, Pet Friendly This home has just been made available for sale, $699,900. Peak Summer Weekly Rates: $3,000 - $3,500 This home has 4 bedrooms and classic Cape Cod decor. All of the modern amenities are included: AC units in all bedrooms, WiFi, flat screen... View all property information
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    Chatham, Cape Cod 02633
    1 / 40
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    A traditional Cape Cod pond-front compound set on a beautifully landscaped 2-acre lot with lovely views of Black Pond. Enjoy summer breezes while relaxing on one of the many patios in this very private yard perfect for lawn games, barbeques or simply stargazing. The main home has 4 bedrooms and 2.5... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 1
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    2016 Rental Rate: $9900 per week, including the cleaning fee ~~ Off-Season: $7400 per week, including the cleaning fee Stunning home in town! Walk to everything on Main Street, as well as kid friendly Oyster Pond Beach, and the playground right across the street! This federal style home is filled... View all property information
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    Chatham, Cape Cod 02633
    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Views-Views-Views! Pet Friendly Cape Cod Vacation Rental home with rooftop deck is just .2 to Ridgevale Beach. Peak Summer Weekly Rates: (last week of June until the first week in September) $3,950/week Pet friendly! Enjoy water views from the main floor living areas and the upstairs master bedroom... View all property information
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    Chatham, Cape Cod 02633
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Enjoy this 3 bedroom, 2 bath Chatham home just minutes from the Cape Cod Rail Trail. The first level of the home features a kitchen with beautiful granite counter tops, separate dining area, living room and a Suite with a full sized bed and full bathroom. The second level has two additional... View all property information
    Location Information
    Chatham, Cape Cod
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    We have a duplex with two side-by-side units with two bedrooms each. Little to no sound passes between the units. Do you like to walk on the beach? We have the best location for it in North America (maybe the world)! A 3 minute walk from the door and you can walk for miles, across a gorgeous salt... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Comfortable 3 bedroom, 2 bath quiet summer retreat only a half mile to downtown Chatham! Peak Summer Weekly Rates: last week of June until the first week in September: $1,800 - $2,200/week. Offering Central AC & Wifi with over 1600 sq. ft. of finished living space, 3 bedrooms, 2 full bathrooms, and... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Pet Friendly! Enjoy this Cape Cod Vacation Rental cottage in Chatham offering 3 bedrooms and 2 baths at the end of a small lane across from the ocean. Peak Summer Weekly Rates: last week of June until the first week in September: $2,500/week. The first floor contains a large living room with flat... View all property information
    Location Information
    Chatham, Cape Cod 02633
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    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
    1 / 17
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This 3 bedroom, 3.5 bath Chatham rental cottage is situated at the end of a cul-de-sac abutting conservation land and only 8/10ths of a mile to popular Ridgevale Beach. Enjoy your day at the beach and then relax on the deck overlooking a wooded area. Amenities include central AC, washer, dryer,... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Pet Friendly. Relax in this 3 bedroom, 2 bath Cape Cod Vacation home in Chatham that is convenient to downtown Chatham and beaches. Peak Summer Weekly Rates: last week of June until the first week in September: $3,200/week. Privacy abounds just off Main Street and the home even overlooks a working... View all property information
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    Chatham, Cape Cod 02633
    1 / 27
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spend your Chatham vacation in this beautiful 4 bedroom, 2.5 bath home located 500 feet from Pleasant Street Beach. This is a truly unique, custom home featuring gorgeous woodwork throughout, a first floor master bedroom with Jacuzzi tub, a bright and beautiful kitchen with granite and silestone... View all property information
    Location Information
    Chatham, Cape Cod 02659
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    1 / 22
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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... View all property information
    Location Information
    South Chatham, Chatham 02695
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    A very well maintained 3 bedroom, 2 bath cottage located just over 1/2 mile to Ridgevale Beach on Nantucket Sound. There is an open and spacious back yard that is great for games and bbq's. Amenties include central AC, washer, dryer, dishwasher, 2 TVs (includes sports and weather), 1 DVD player,... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    3 of 5 stars (2) Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    This Chatham cottage has a cozy, comfortable living /dining area and three bedrooms. There is a large, sunny deck with table and chairs for outdoor dining and a picnic table on the shady side of the house. The two dedicated parking spaces make for easy parking. It is a short walk to beautiful... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    This tastefully decorated 3 bedroom, 1 bath South Chatham vacation cottage is only 2/10ths of a mile to Forest Beach. There are two bedrooms on the first floor and an open floor plan with wood floors throughout. The additional bedroom is on the upper floor with a slider out to a deck. Relax on the... View all property information
    Location Information
    South Chatham, Chatham 02569
    1 / 6
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
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    • Waterfront
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    • x
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    About this property
    Cape cod home on the shores of South Chatham. The main floor constists of an eat in kitchen, living room / dining room with three picture windows, a brick fireplace, a four window reading room facing the ocean, and a full bathroom with an accessable shower. The upstairs sleeping area has a master... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Porch
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    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 SPECIAL : $1000 a night for a short stay - min 3 nights between Aug 14-19, 2016!! Pet friendly for Dogs only-ask your rental specialist... View all property information
    Location Information
    Chatham, Cape Cod 02650
    1 / 14
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Charming 3 bedroom, 1 bath cottage with views of Nantucket Sound from the rooftop deck. There is a good sized backyard and Forest Beach is just 3/10ths of mile away. Amenities include a window AC unit in each bedroom, cable TV (with basic cable only; no NESN, ESPN, Weather Channel, etc.) with a DVD... View all property information
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    South Chatham, Chatham 02659
    1 / 14
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Enjoy your Chatham vacation in this 3 bedroom, 2 full bathroom house that is only 2/10th of a mile from Pleasant Street Beach on Nantucket Sound. It offers window AC units in the second floor bedroom, washer, dryer, dishwasher, microwave, cable TV (includes sports and weather) DVD player, Wi-Fi,... View all property information
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    South Chatham, Chatham 02659
    1 / 38
    5 of 5 stars (1) Excellent
    9 Bedrooms, 5 Bathrooms, Sleeps 20 | Quick View
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    • x
    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 / 27
    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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. Just under a mile to town, this coastal Cape is located in a quiet, family... View all property information
    Location Information
    Chatham, Cape Cod 02633
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
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    About this property
    Light and bright home with pretty marsh views! Great, central location, close to Hardings Beach and a quick drive into downtown Chatham! You will love the screened porch or back deck for relaxing. AC units in every bedroom for the hot days, if you aren't at the beach! One bedroom on the first level... View all property information
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    Chatham, Cape Cod 02633
    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Our home is the perfect spot for your family to enjoy beautiful Cape Cod and award winning Chatham. Located on a picturesque and VERY quiet street you can stroll to Pleasant Street Beach or Forest Street Beach. The yard offers the perfect place for the kids to play, the upper and lower decks offer... View all property information
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    Chatham, Cape Cod 02659
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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... View all property information
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    Chatham, Cape Cod 02633
    1 / 29
    5 of 5 stars (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This 5 bedroom, 3 bath Chatham rental home has incredible water views of Taylor's Pond and is only 6/10ths of a mile to Cockle Cove beach by path. It is surrounded by oak trees creating a very private setting. There is a wonderful deck to lounge on, bbq on the gas grill or just take in the... View all property information
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    Chatham, Cape Cod 02659
    1 / 15
    4 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Our Pleasant Street home is a charming 3 bedroom, 2 bath year-round home which is located at 320 Pleasant Street in South Chatham and it can comfortably accommodate up to 8 people. It is only a 2 minute walk to Nantucket Sound, the warm water side of Cape Cod! There is no beach sticker required... View all property information
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    Chatham, Cape Cod 02659
    1 / 17
    4 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    2016 Rental Rate: $10,675 per week with the cleaning and linens included. Weekly rentals from mid-JUNE to mid-SEPT The views from this sprawling Crows Pond waterfront Cape, are incredible. You can see water from almost every window of this 4 bedroom, 5,400 square foot home with private dock. This... View all property information
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    Chatham, Cape Cod 02633
    1 / 30
    5 of 5 stars (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • x
    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 / 5
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    2016 Rental Rates ~ TWO WEEK MINIMUM! TWO WEEKS: $11,275 with the cleaning fee included Off-Season: $8275 TWO WEEKS with the cleaning fee included This property has $1,000 refundable security deposit Featuring views of Chatham Harbor and just steps to Claflin Landing, this classic Cape-style... 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
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    5 of 5 stars (2) Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Children's Pool
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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 four bedroom, five and a half bathroom double end townhouse with gorgeous direct water views of Oyster Pond. Townhomes 31 and 32 are rented... 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
    This charming Cape Cod style cottage is a delight! It is a 2 bedroom, 2 bath home (one large new one) on a large lot with much privacy. It has A/C, hi-speed wireless internet,a new wide-screen HD TV, new carpeting throughout the house, is on a no-outlet street so it is safe for children and is... View all property information
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    Chatham, Cape Cod 02659
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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 just a hop, skip and a jump... View all property information
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    Chatham, Cape Cod 02633
    1 / 26
    3.5 of 5 stars (2) Average
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    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: $4500- $6,500/week. This spot is a boater's paradise! From... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    4.5 of 5 stars (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    At this quiet lakeside cottage you can experience classic Cape Cod with all the modern amenities -- wireless internet, cable TV, air conditioning. Enjoy beautiful sunsets as well as swimming and canoeing at the lake---and only be a short trip to the beach or Chatham center. The cottage features... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Located SALT WATERFRONT on the Oyster Pond River, a salt water Nantucket Sound inlet, this charming, beautifully updated home, has views of both Nantucket Sound and the Village of Chatham. The private neighborhood is ideal for biking, morning walks and evening strolls. Swimming, boating and... 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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    454 Training Field Road CHATHAM Lovely updated 3 bedroom home in close proximity to Pleasant Bay and Jackknife Cove beach. Just a few minutes drive to the quaint downtown village of Chatham. This home rents for $1600 per week in season. All rates plus $60 Handling Fee and $55 Vacation Damage... View all property information
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    Chatham, Cape Cod 02633
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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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... View all property information
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    Chatham, Cape Cod 02633
    1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Porch
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    $1150/week-High Season-lower other times Foote-steps Chatham Charmer - Weekly Rentals The charm of a Cape Cod cottage with all the amenities of home. Relaxation and conveniences on a private circle with idyllic nature views... Enjoy our enclosed porch overlooking the salt marsh and a short (4/10... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Pet Friendly! Spend Lazy summer days at this Cape Cod Vacation rental in Chatham. Peak Summer Weekly Rates: last week of June until the first week in September: $3,400/week. With the shade from the pines, the spray of sea salt from the Nantucket Sound and the warm summer sun, you are sure to have a... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    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
    Location Information
    Chatham, Cape Cod 02633