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Holiday Rentals in Chatham, MA

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 17
    4.5 of 5 bubbles (2) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 22
    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 11
    4 of 5 bubbles (1) Very good
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    This light and bright 3 bedroom, 2 bath ranch is located directly across from White Pond, a large fresh water pond great for swimming, paddle boarding, kayaking or fishing. It is also adjacent to the Old Colony Rail Trail (bike path) for easy access to downtown Chatham or to the Cape Cod Rail Trail... View all property information
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    Chatham, Cape Cod 02633
    1 / 10
    Studio, 2 Bathrooms, Sleeps 11 | Quick View
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    209 Champlain Rd Chatham MA DOG FRIENDLY Great, rambling home with an old-Cape Cod feel located on the "loop" just around the bend from Stage Harbor. Wonderful area to enjoy while here on the Cape! A tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $3575 per week including the cleaning fee. ~~ Off-season: $2575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming home right on Seaview Street - a short walk to downtown Chatham, or Chatham Bars Inn! This home has lovely furnishings throughout,... View all property information
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    Chatham, Cape Cod 02633
    1 / 24
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to: Sandy Paws! Pet Friendly. Come have some fun in the sun at this Cape Cod Vacation home 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... View all property information
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    Chatham, Cape Cod 02633
    1 / 8
    5 of 5 bubbles (2) Excellent
    South Chatham
    9 Bedrooms, 4 Bathrooms, Sleeps 20 | Quick View
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    About this property
    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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    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    ID #MARSH4 Dog Friendly and Now with A/C and WIFI Internet! [~]This 3.5 bedroom and 2 full bath vacation home in Chatham with beautiful marsh views is just a half mile from HARDINGS BEACH and Oyster Pond River/ The Chatham Kayak Co. This home offers such amenities as a washer/dryer, 3 A/C units,... View all property information
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    Chatham, Cape Cod 2633
    1 / 12
    5 of 5 bubbles (4) Excellent
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    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
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    1 / 13
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    The location of this cottage is ideal ~ it's nestled off the main road between downtown Chatham and Andrew Hardings Beach. This is a quaint 2 bedroom 1.5 bath house. Close to fine restaurants, Chatham band concerts, ball games, the beach, the lighthouse and much, much more. Amenities include... View all property information
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    Chatham, Cape Cod 02633
    1 / 18
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    This recently renovated 4 bedroom, 2 bath house has a bright open floor plan with new furnishings throughout. This comfortable home is situated in a wonderful neighborhood with a great yard for children and is only 5/10ths of a mile from Nantucket Sound Beaches. A queen bedroom and a twin bedroom... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 7
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    16 ELLIS Pet friendly home in Chatham sleeps 4. Two bedrooms one with a queen and bedroom two has a queen and a single bed. Outdoor seating on the deck is spacious. Enclosed outside shower. One and a half baths. WiFi. A/C in the bedrooms. A short drive to Harding beach. FRIDAY arrival and... View all property information
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    Chatham, Cape Cod 02633
    1 / 24
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    #604 The Hideaway: Less than a mile to one of the best beaches in Chatham! Feel the warm sand between your toes at Cockle Cove beach, just .8 mile walk/bike ride. Downtown Chatham just minutes away. The Hideaway lives up to its name with being tucked away at the end of a private road, completely... View all property information
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    Chatham, Cape Cod 02633
    1 / 17
    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Enjoy your Cape Cod vacation in this tastefully decorated, comfortable home. It is located in Hardings Beach Hills, only 4/10ths of a mile from popular Harding's Beach. This 3 bedroom, 2.5 bathroom home has an updated kitchen with granite countertops and stainless steel appliances as well as... View all property information
    Location Information
    Chatham, Cape Cod 02669
    1 / 28
    Studio, 4 Bathrooms, Sleeps 13 | Quick View
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    About this property
    Water Views Near Chatham Light, Guest Apartment, Sleeps 11 (Linens Included) Pets Considered Peak Summer Weekly Rates: $7,500 - $8,700 (Rents Saturday to Saturday during peak season) This classic home is perched in the dunes of Chatham, just to the south of Chatham Light. This large home is ideal... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    4 of 5 bubbles (2) Very good
    South Chatham
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Enjoy your Chatham vacation in this 3 bedroom, 2 bathroom house that is only 2/10th of a mile from Pleasant Street Beach on Nantucket Sound. This traditional Cape home features two bedrooms on the first floor and 2 bedrooms on the 2nd floor. The living room and kitchen lead to a second light and... View all property information
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    South Chatham, Chatham 02659
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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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 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
    Location Information
    Chatham, Cape Cod 02633
    1 / 22
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    #603 - Lovers Holley Home: Lovely renovated home less than one mile from Chatham's famous downtown shopping and overlooking Lover's Lake - which is a walk around corner in a few minutes. All Chatham beaches are within two miles.  This home, located in the Great Hills Estates, provides a very... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 12
    4 of 5 bubbles (1) Very good
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    Enjoy this classic 3 bedroom, 1 full bath Cape beach cottage only 3/10ths of a mile to popular Ridgevale Beach. Amenities include washer, dryer, dishwasher, two window AC units (one in the Queen bedroom and one in the bedroom with 2 Twins), cable TV (includes sports and weather), DVD player, Wi-Fi,... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 13
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $2475 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Take advantage of an easy walk to Hardings Beach from this light and bright updated ranch. The kitchen has been opened up with new appliances and finishing touches. There is a fantastic screened in... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Spend your Cape Cod vacation in this 3 bedroom, 2 bathroom rental home close to the downtown area, fish pier, ball field, playground and bakeries. Upgrades for 2017 include new queen mattresses in both bedrooms and new landscaping. Amenities include central AC on the 1st floor and window units in... View all property information
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    Chatham, Cape Cod 02633
    1 / 17
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    This 3 bedroom, 3.5 bath home is situated at the end of a cul-de-sac and only 8/10ths of a mile to popular Ridgevale Beach. The spacious master bedroom with queen bed is on the first floor while the other 2 bedrooms and full bathroom are on the 2nd floor. The finished lower level has a sitting area... View all property information
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    Chatham, Cape Cod 02659
    1 / 26
    North Chatham
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    Luxury Chatham Home, Water Views, Private Beach Peak Summer Weekly Rates: $5,150-$5,950 (Rents Saturday to Saturday during peak season) The 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... View all property information
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    North Chatham, Chatham 02650
    1 / 13
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2017 Rental Rate: $2100, including the cleaning fee Off-Season $1600 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This is a well maintained property located in a quiet area in W. Chatham. Spacious bedrooms, one with two double beds. Updated kitchen, with a skylight,... View all property information
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    Chatham, Cape Cod 02633
    1 / 12
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
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    • Private Garden
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    Beautiful new condominium nestled on tranquil Perch Pond, located just a half mile from down town Chatham. This unit boast all the amenities of luxury living. Central A/C, gas fireplaces and granite tops to name a few. Spend your afternoons relaxing on the back deck overlooking the pond after a... View all property information
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    South Chatham, Chatham 02633
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Panoramic views of Nantucket Sound from this traditional 4 bedroom, 2 full bath Cape beach house with direct access to a private beach. Living space abounds on the first floor with multiple sitting areas, large dining area and furnished deck. A master bedroom with queen bed is also located on the... View all property information
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    Chatham, Cape Cod 02659
    1 / 41
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Beachfront townhome! Sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outermost Harbor and Little Beach. Bike to town or the Monomoy Wildlife Refuge.​ Central AC and WiFi too. 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
    1 / 32
    Studio, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Come stay at: Cape Sunsations! Views- Views- Views from every room! Updated Luxury Waterfront Cape Cod Vacation Rental Home In Chatham, offering over 3100 square feet of living space. Peak Summer Weekly Rates:  last week of June until the first week in September: $4,900/week. Updated Luxury... View all property information
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    Chatham, Cape Cod 02633
    1 / 30
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    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: $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
    1 / 17
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Enjoy views of Nantucket Sound from every floor of this recently updated, lovingly and meticulously maintained, 3 bedroom, 2 bathroom Chatham rental property. It is a perfect balance between having all of the modern amenities, with an open, light and bright feel while still maintaining the true... View all property information
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    Chatham, Cape Cod 02659
    1 / 28
    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Coastal, seaside home offering Central air has plenty of room for 3 couples or 2 families. Walk to beach and town! Peak Summer Weekly Rates:  last week of June until the first week in September: $3,100/week. This Cape Cod Vacation Rental in Chatham has an open floor plan with 3 bedrooms on the main... View all property information
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    Chatham, Cape Cod 02633
    1 / 37
    4 of 5 bubbles (1) Very good
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Come Stay at: Mis Behavin! Pet Friendly! Charming, fully renovated Sea Captain's home, located in downtown Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $5,000/week Enter through the sun porch offering extra dining- directly into the gourmet kitchen with a... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    Studio, 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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    Studio, 11 Bathrooms, Sleeps 16 | Quick View
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    • Hot Tub
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    Rising majestically over Eldridge Point, overlooking Oyster River, Harding’s Beach, and Nantucket Sound, this extraordinary estate features the largest private shoreline in Chatham. Watch glorious sunsets while swimming in your infinity edge pool; or cook dinner in the outdoor kitchen while friends... View all property information
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    Chatham, Cape Cod
    1 / 28
    South Chatham
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    This rental is a comfortable 3 bedroom, 2 bath that sleeps 8. It sits on a pretty lot with a big backyard just 7/10th of a mile to Forest Beach in Chatham. A sunporch off the kitchen is great for that morning cup of coffee and the large deck has a gas grill for evening barbeques. The kitchen is... View all property information
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    South Chatham, Chatham
    1 / 12
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    Located in the heart of Chatham Village with its many delightful shops, galleries, and restaurants this 2 bedroom home is close to everything Chatham has to offer. Enjoy a short stroll to Lighthouse Beach, the Chatham Fish Pier, tranquil Mill Pond or the Orpheum Theatre. The first floor offers a... View all property information
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    Chatham, Cape Cod 02633
    1 / 29
    5 of 5 bubbles (2) Excellent
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    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 / 22
    Studio, 3 Bathrooms, Sleeps 9 | Quick View
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    • Outdoor Dining Area
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    About this property
    Paradise Found at this special retreat in this Cape Cod Vacation home Rental in Chatham called the Heron's Nest! Peak Summer Weekly Rates:  last week of June until the first week in September: $4,600/week. This spacious , Four Bedroom, 3 bath luxury Chatham Rental will surely delight you in every... View all property information
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    Chatham, Cape Cod 02633
    1 / 19
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    $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
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This lovely and bright South Chatham rental home is situated in a great neighborhood and only 3/10ths of a mile to Forest Beach on Nantucket Sound. There are four bedrooms with newer beds and two and a half baths, a family room upstairs and an open kitchen/dining area. Enjoy a barbeque on the... View all property information
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    Chatham, Cape Cod 02659
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Come stay at: Starfish Beach Cottage! 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... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 9
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy your summer vacation in this charming 3 bedroom, 2 bath home that is located 7/10ths of a mile to Nantucket Sound beaches and 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 central AC, washer, dryer,... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 25
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to Sea Glass! 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... View all property information
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    Chatham, Cape Cod 02659
    1 / 24
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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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    5 of 5 bubbles (1) Excellent
    Studio, 7 Bathrooms, Sleeps 16 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Chatham, Cape Cod 02633
    1 / 21
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    169 Lime Hill Road CHATHAM This magnificent and well-appointed home is the epitome of luxury living with added Cape Cod style. Conveniently located less than 3/4 of a mile from Chatham Village, you also have deeded rights to a path to Oyster Pond.. Every amenity is provided, from central air to... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    Studio, 3 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Enjoy staying in the heart of Chatham Village in this new, tastefully appointed 2 bedroom, 2.5 bath 1,300 sq. ft. home. Downtown Chatham is just steps away where you can enjoy shopping, fine restaurants, band concerts, ball games and much, much more. This home is only 2/10th's of a mile to Oyster... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 27
    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
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    Chatham, Cape Cod 02659
    1 / 18
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy fantastic, unobstructed views of Red River Beach and Nantucket Sound from this 3 bedroom, 2 full bath traditional Chatham vacation rental only 1/10th of a mile to a semi-private beach. The property comfortably accommodates 8 people however can take up to 10 with the use of the full-size sleep... View all property information
    Location Information
    Chatham, Cape Cod 02659