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Vacation Rentals in Chatham, MA

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    Travellers to Chatham are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
    1 / 7
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    73 Main Street, Unit #8 Charming second-story condominium apartment located right across the street from Lighthouse Beach. Views of the beach from deck off the living room. Walk across the street to Lighthouse Beach and also within walking distance to the Village. NO pets accepted. $1350 per week,... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 8
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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
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    Chatham, Cape Cod 02633
    1 / 28
    South Chatham
    3 Bedrooms, 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 (.6 mile)! Central air, WIFI, a Screened... View all property information
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    South Chatham, Chatham 02659
    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This Cape Cod Vacation Rental home is just .2 miles from Pleasant Street Beach in Chatham. Peak Summer Weekly Rates:last week of June until the first week in September: $2,900/week. Warm water, sunsets, and miles of beach on Nantucket Sound awaits you just around the corner. This family friendly... View all property information
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    Chatham, Cape Cod 02659
    1 / 20
    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 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    04/01/17 - 06/24/17 $1,700 06/24/17 - 07/01/17 $2,100 07/01/17 - 08/26/17 $2,900 08/26/17 - 09/02/17 $2,000 09/02/17 - 10/28/17 $1,700 Enjoy the convenient location of this 3 bedroom, 2 full bathroom classic Cape style Chatham rental home close to downtown Chatham, Oyster Pond, and Clafflin... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $3,600/week Peak Season (July 1- September 2) $1,900/wk for the weeks of (6/24 and 9/2) $1,600/week Shoulder Season (6/17 and 9/9) $1,400/week Shoulder Season (6/10 and 9/16) $1,200/wk (before 6/10 and After 9/23) This light, bright two bedroom two bath Chatham rental cottage has panoramic views of... 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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    About this property
    Come to the Cape and enjoy this 3 bedroom, 2 bath Chatham rental home. Take time to relax on the expansive deck with wonderful views of Mill Creek and Nantucket Sound or enjoy a BBQ on the gas grill. The open floor plan with adjoining kitchen, dining and living rooms creates a spacious area perfect... View all property information
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    Chatham, Cape Cod 02659
    1 / 28
    5 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
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    • Balcony
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    Water Views Near Chatham Light, Guest Apartment, Sleeps 11 (Linens Included) Pets Considered Peak Summer Weekly Rates: $7,500 - $8,700 This classic home is perched in the dunes of Chatham, just to the south of Chatham Light. This large home is ideal for larger groups looking for a perfect Chatham... View all property information
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    Chatham, Cape Cod 02633
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    5 Bedrooms, 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) Located in a premier Chatham Village location, this classic antique home has everything to experience an idyllic Chatham vacation. Park your car in the driveway and leave it... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This wonderful 3 bedroom, 2 bath house is in a quiet neighborhood yet is close to shopping, restaurants and beaches. There is access to a nearby path leading to Ridgevale Beach (about 8/10ths of a mile long) and this home is also only a short drive to Hardings Beach. Amenities include window AC... View all property information
    Location Information
    Chatham, Cape Cod 02669
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Pet Friendly. Come have some fun in the sun at this Cape Cod Vacation cottage in Chatham! You will enjoy deeded access to the 'Little Beach flats'. A Complete Renovation is taking place over the Winter-Everything will be 'all new'! Peak Summer Weekly Rates:last week of June until the first week in... View all property information
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    Chatham, Cape Cod 02633
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    5 of 5 bubbles (2) Excellent
    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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    4 of 5 bubbles (1) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    This rental property boasts both a main house and fully equipped cottage, great for extended family or friends. The main house has 3 bedrooms and 1 full bath. Amenities include central AC on the first floor and window AC units in the upstairs twin bedroom, washer, dryer, dishwasher, TVs with... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 11
    North Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
    Location Information
    North Chatham, Chatham 02650
    1 / 9
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    This traditional 2 bedroom 1 bathroom Chatham cottage is located in a quaint neighborhood and is just 4/10ths of a mile to Pleasant Street Beach. Amenities include a window AC unit in each bedroom, cable TV (with basic cable only), microwave, outside dining table with gas grill and an enclosed... View all property information
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    Chatham, Cape Cod 02659
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    1 / 18
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    You'll be only 5/10th's of a mile to popular Cockle Cove Beach at this 4 bedroom, 1.5 bathroom Chatham house. Amenities include washer, dryer, dishwasher, window a/c units in each bedroom and one in the living room, cable TV (includes sports and weather),DVD player, Wi-Fi, gas grill, deck with... 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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    Enjoy your summer vacation in this charming 3+ bedroom 2 bath home that is located 7/10ths of a mile to Nantucket Sound beaches. Situated just 2/10ths of a mile to Mill Creek which is great for kayaking and canoeing into Nantucket Sound or Taylor's Pond. Amenities include washer, dryer, dishwasher,... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 37
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    Pet Friendly! Nothing beats this luxury 4 bedroom, 4.5 bath Vacation Rental located in the heart of Chatham’s historic village!! Peak Summer Weekly Rates:last week of June until the first week in September: $9,100 - $9,400/week Whether you are soaking in the hot tub on the private patio or enjoying... 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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    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 this "fan favorite" Cape Cod Vacation... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Why not stay at our Chatham home this summer? Peaceful and inviting, our cape-style home is in a very picturesque area of Chatham. Come relax in our breezy screened porch or enjoy the warm Nantucket Sound waters of Pleasant and Forest Beaches which are a five minute walk (3/10 mi). Leave your car... View all property information
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    Chatham, Cape Cod 02633
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    Renovated Sea Captain's Home by Ryder's Cove, Pet Friendly 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 TV with digital cable, washer/dryer, and a completely... View all property information
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    Chatham, Cape Cod 02633
    1 / 23
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Located on the Stage Harbor ?loop', this very private, quintessential Chatham 4-acre retreat has been recently renovated and has all new furnishings and amenities. The home is surrounded by mature plantings and conservation land and has views of Stage Harbor from the second floor master bedroom.... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Cape cottage near wonderful Hardings beach Nice location about a third of a mile to popular, scenic Harding s beach. Typical knotty pine style cottage with central living room and enclosed rear porch open to the picnic patio. Has a small front deck too. Sleeps 6. $1500 per week plus $60 handling... View all property information
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    Chatham, Cape Cod 02633
    1 / 35
    4 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    Immaculate Chatham Village Renovation, Walk to Beach & Village Peak Summer Weekly Rates: $7,900-$8,800 (Linens Included) Your quintessential Chatham vacation awaits! This masterfully restored classic is situated in the heart of Chatham with the beach across the street and a 5 minute walk to town.... 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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    Find your Pathway to Peace! Waterfront 3 bedroom, 2 bath vacation rental cottage is located right on the beach in Chatham, the best of Cape Cod. Peak Summer Weekly Rates:last week of June until the first week in September: $4,600/week. Perfect for a relaxing getaway, this cottage is steps away from... View all property information
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    Chatham, Cape Cod 02633
    1 / 26
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Enjoy easy resort style living in this newer Cape Cod Vacation Rental home in Chatham. Peak Summer Weekly Rates:last week of June until the first week in September: $3,600/week. This home is in its own residential sub division and is close to beaches, restaurants, downtown and includes a community... 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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    Stay in the heart of Chatham Village in this well-maintained 3 bedroom 1.5 bathroom home. Situated in a quiet neighborhood only 4/10ths of a mile from the shops and restaurants on Main Street, baseball field, playground and the Fish Pier. This traditional Cape home features a queen bedroom on the... View all property information
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    Chatham, Cape Cod 02633
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    5 of 5 bubbles (6) Excellent
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    This immaculate two-bedroom/one-bath cottage sleeps five and is cozy and affordable. It's located one-half mile from Cockle Cove Beach on warm Nantucket Sound. Situated on a quiet cul de sac with a nearby childrens playground, this property is protected and cooled by pine trees and salty breezes.... View all property information
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    South Chatham, Chatham 02659
    1 / 15
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    OFF SEASON DISCOUNT is $125/night for 2 people, $15/night per additional person. Please see "Rates." (Does not include holidays.) The ''Chatham Retreat'' is clean, charming, and tastefully decorated. 1/5 mile walk to beautiful beach. You will enjoy this quiet neighborhood and lovely yard with... View all property information
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    Chatham, Cape Cod 02659
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    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    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,wifiand more. In historic... View all property information
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    Chatham, Cape Cod 02633
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This recently 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 2017... View all property information
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    Chatham, Cape Cod 02633
    1 / 41
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beachfront condo! Sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outer Most Harbor Little Beach-bike to town or Monomoy Wildlife Refuge.​ CENTRALA/C and WIFI too. 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 / 33
    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) $4,050/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 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 1 | Quick View
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    Amazing spot to spend your summer vacation! Drive past Eastward Ho Golf Club and just keep going until you're at the water. This adorable cottage is clean and comfortable. Wake up to views and the sounds of the sea. This wonderful home is waiting for your flip flops and beach towels. Two bedrooms... View all property information
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    Chatham, Cape Cod
    1 / 12
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
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    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 / 14
    5 of 5 bubbles (1) Excellent
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy your vacation in this bright, open 3+ bedroom, 2 bath Chatham home on a cul-de-sac in a pleasant neighborhood. This home is only one-half mile to Cockle Cove Beach or 2/10th's of a mile to Taylor's Pond where you can launch a kayak to paddle into Nantucket Sound. New furnishings include a... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 22
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Views galore from this two bedroom one bath cottage nestled along a saltmarsh only 500 feet from the semi private association beach on Nantucket Sound. A perfect getaway for nature lovers and bird watchers. Newly renovated kitchen and interior includes granite countertops, stainless steel... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 19
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Porch
    • Washer
    • Grill
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    $7,200/week Peak Season (July 22 - August 18) $6,800/week On Season (7/1, 7/8, 7/15, 8/19 and 8/26) $5,000/week Off Season (week of June 24 and Sept 2) $4,300/week Off Season (week of June 17 and Sept 9) $3,600/week Off Season (before June 16 and after Sept 15) Spectacular 3+ bedroom, 3.5 bath home... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
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    • Smoking allowed
    • x
    About this property
    Enjoy your summer vacation in this charming bright, contemporary home just 1/2 of a mile to Pleasant Street and Red River Beaches. This 3 bedroom, 2 bath home was fully renovated in 2007 including bathrooms, kitchen and flooring. Enjoy furnished multi-level decks with a gas grill, nice yard and an... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Terrace
    • DVD Player
    • Grill
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    4 Bedroom, very bright, beachy home with SEPARATE guest house! This home comes equipped with AC, fully stocked kitchen and deck to enjoy your wine/coffee. Not to mention a private enclosed lawn to relax or play on. Located in the HEART OF TOWN. Walk out the driveway and you will find yourself... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 21
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Patio
    • Grill
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Chatham, Cape Cod 02659
    1 / 15
    4 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Grill
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 / 12
    West Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Washer
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy this updated 2 bedroom, 1 bath Chatham vacation cottage with views of Oyster River. The open kitchen, dining and living room has a slider leading out to a large deck with chaise lounges, dining table with umbrella, gas grill and enclosed outside shower. Amenities include window AC units in... View all property information
    Location Information
    West Chatham, Chatham 02669