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Chatham Summer Rentals

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    1 / 6
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Tradition and modern luxuries collide at this lovely Cape Cod home. You'll find high-end furnishings inside and beach access nearby! You're on a quiet lot near a salt marsh and just a half mile from Forest Beach and less than two miles from lovely Taylors Pond. Post-and-beam construction can be... View all property information
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    Chatham, Cape Cod 02659
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Satellite TV
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    If you're searching for the perfect homebase for your next Cape Cod getaway, look no further than this spacious 4-bedroom, 3-bathroom Chatham vacation rental house! Boasting 2,600 square feet of tastefully appointed living space, with accommodations for up to 11, this lovely home is within close... View all property information
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    Chatham, Cape Cod 02659
    1 / 33
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    About this property
    Featuring gorgeous gardens and outdoor spaces to explore, a luxurious and updated interior, and all the comforts of home, this beautiful rental has it all! Ideal for two guests, this would be a fantastic place for a honeymoon, couples getaway, or even a relaxing solo retreat. Nestled in a quiet... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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 two bedroom, three full bathroom end-unit with gorgeous direct water views of Oyster Pond. Beautifully decorated with charming interior decor.... View all property information
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    Chatham, Cape Cod 02633
    1 / 35
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Experience a glimpse of Cape Cod waterfront living at this three-bedroom Chatham home, a dog-friendly property with a wrap-around deck, panoramic views of the ocean and Oyster River, and nearby access to Harding's Beach. This quaint two-level home is scenically situated between Nantucket Sound and... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Beautiful two bedroom plus a den and a loft, two and a half bathroom townhome with gorgeous direct water views of Oyster Pond. Beautifully decorated with... View all property information
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    Chatham, Cape Cod 02633
    1 / 25
    5 of 5 bubbles (2) Excellent
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Lovingly renovated in winter 2013 and designed by a New York couple, this 4-bedroom, 3-bathroom colonial saltbox home evokes the style and taste of classic Americana, decorated with vintage finds and unique antique pieces. Whether you’re on a family vacation, couples getaway, or a reunion with... View all property information
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    South Chatham, Chatham 02659
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    1 / 24
    South Chatham
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This gorgeous sprawling home on 3 acres is surrounded by 50 acres of conservation land. It is extremely private, very quiet, has its own pond, and plenty of space for sunbathing and outside play, large, expansive decks, lots of room for entertainment inside and out. It is completely equipped with... View all property information
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    South Chatham, Chatham 02659
    1 / 24
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    About this property
    Escape to this 1801 Sea Captain's House with alluring old-world charm in Chatham for the ultimate Cape Cod getaway! With 5 bedrooms,4.5 bathrooms and accommodations for 10 this vacation rental house is the ideal size for families, friends, or couples traveling together. Whether you're seeking... View all property information
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    Chatham, Cape Cod 02633
    1 / 12
    5 of 5 bubbles (5) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. This is a stunning four bedroom, four and a half bath spacious end-unit townhouse with spectacular views of Oyster Pond. Unit 25 is the largest... View all property information
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    Chatham, Cape Cod 02633
    1 / 28
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Children's Pool
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    • Hot Tub
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    About this property
    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
    1 / 23
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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 / 40
    5 of 5 bubbles (2) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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
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    Chatham, Cape Cod 02633
    1 / 25
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Spectacular seaside views from almost every room in this beautiful 4 bedroom, 3 bathroom Chatham rental home which rests below the watchful gaze of Chatham Light. This Chatham rental home is ideally situated between scenic Lighthouse Beach and the edge of Monomoy National Wild Life Refuge, a beach... View all property information
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    Chatham, Cape Cod 02633
    1 / 22
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    $5,900/week Peak Season (July 1 - September 1) $3,400/wk for the weeks of (6/17, 6/24 and 9/2, 9/9) $2,500/wk (before June 17 and after September 16) Located close to Chatham Village and Oyster Pond this custom built Cape has a well laid-out floor plan with 3+ bedrooms, 4.5 baths and plenty of... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    4 of 5 bubbles (2) Very good
    South Chatham
    3 Bedrooms, 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
    1 / 31
    4.5 of 5 bubbles (2) Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Central Air and Pet Friendly! Totally Updated 5 Bedroom Cape Cod Vacation Rental Family Home in Chatham on the way to Cockle Cove Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,800- $4,200/week. Large family? No problem! Can't leave home without Fido?... View all property information
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    Chatham, Cape Cod 02633
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    1 / 29
    5 of 5 bubbles (2) 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 / 18
    4.5 of 5 bubbles (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This recently renovated 3+ bedroom, 2 1/2 bath house is just 2/10ths of a mile from popular Ridgevale Beach. Common space abounds with two living areas, a den and a sun room, all on the main floor. The newly remodeled kitchen is quite spacious and has all new appliances. The master bedroom with... View all property information
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    Chatham, Cape Cod 02633
    1 / 39
    6 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    $13,500.00/week Peak Season (7/15 - 8/19) $12,500.00/week On Season (7/1 - 7/15 and 8/19 - 9/2) $11,500.00/week Off Season Gorgeous panoramic views of Stage Harbor, Nantucket Sound and Outermost Harbor from every room in the house. Private dock, multiple decks, a swimming pool and an incredibly... View all property information
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    Chatham, Cape Cod 02633
    1 / 12
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 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
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    Chatham, Cape Cod 02659
    1 / 21
    5 of 5 bubbles (1) Excellent
    South Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    South Chatham, Chatham 02659
    1 / 18
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Enjoy your Chatham vacation in this well appointed, light and bright, updated 4 bedroom, 3 1/2 bath, water-front home with breathtaking views of Pleasant Bay, North Beach and the Atlantic beyond. The comfortably furnished patio overlooks a small cove in Pleasant Bay were you can easily launch your... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $3,500/week Off Season (5/1 - 6/30 and 9/2 - 10/31) $5,200/week Peak Season (7/1 - 8/18) $4,900/week Shoulder Season (8/19 - 9/1) Enjoy your vacation in this private setting with a water view and only a short walk to downtown Chatham. This well appointed, light and bright, 4 bedroom, 2 1/2 bath... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This brand new Chatham home is conveniently located only 6/10ths of a mile from Forest Beach. The gleaming hardwood floors and open floor plan give this home a light and airy feel and the dining area opens to a spacious furnished deck for relaxing afternoons or an alfresco dinner after a long day... View all property information
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    Chatham, Cape Cod 02659
    1 / 19
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    $13,200 /week Peak Season (July 1 - September 2) $9,100/wk for the weeks of (6/24 and 9/2) $7,800/week Shoulder Season (6/17 and 9/9) $6,800/week Shoulder Season (6/10 and 9/16) $6,100/wk (before 6/10 and After 9/23) Spend your Chatham vacation in this beautiful brand new 4 bedroom 4.5 bath home... View all property information
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    Chatham, Cape Cod 02659
    1 / 17
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Just steps away from Forest Beach this 3 bedroom, 3 bath home boasts wonderful views of Nantucket Sound from the three decks, main living area and the two upstairs bedrooms. The first floor den has a queen sleep-sofa and large flat-screen TV. The third bedroom and bathroom are located in an... View all property information
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    Chatham, Cape Cod 02659
    1 / 12
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 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
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    Chatham, Cape Cod 02633
    1 / 36
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    05/20/17 - 06/24/17 $7,300 06/24/17 - 07/01/17 $8,000 07/01/17 - 09/02/17 $10,500 09/02/17 - 09/09/17 $8,000 09/09/17 - 09/30/17 $7,300 This beautifully renovated 1850 Antique home is literally just steps to Andrew Hardings Beach and Lighthouse Beach via a path directly across from the house. This... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    Chatham, Cape Cod 02669
    1 / 29
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Spectacular rental property. This newer and very spacious 4 bedroom, 4.5 bathroom home offers plenty of space with it's soaring ceilings, spacious bedrooms and large back yard. Centrally located in a wonderful neighborhood of higher-end homes this rental includes use of the association pool and... 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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    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
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    This 3 bedroom, 3 bath Chatham home has multiple decks overlooking Mill Creek, the salt marsh and Nantucket Sound. Stairs leading to the creek allow you to launch a kayak or paddleboard and paddle into Nantucket Sound right from the property. The house is only .5 mi walk or drive to Cockle Cove... View all property information
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    Chatham, Cape Cod 02659
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 / 31
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    $12,400/week Peak Season (July 2nd - September 3) $8,400/wk for the weeks of (6/25 and 9/3) $7,700/week Shoulder Season (6/18 and 9/10) $6,100/week Shoulder Season (6/11 and 9/17) $5,500/wk (before 6/11 and After 9/24) This beautifully refurbished Chatham rental house has a path that leads to a... View all property information
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    Chatham, Cape Cod 02633
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Parking
    • Satellite TV
    • Waterfront
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    • Outdoor Dining Area
    • Patio
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    • Pet-friendly
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    • x
    About this property
    Welcome to: Seaside Stroll! Beachfront Condo! 3 Bedrooms, sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outermost Harbor, Little Beach, or bike up to the village of Chatham. Easy bike ride to Lighthouse Beach and Monomoy Wildlife Refuge!  Central AC... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This is a truly beautiful home situated in a sought after Chatham beach community. You'll find a well appointed 4 bedroom, 4 bath home with a path leading directly to Hardings Beach. You can practice your putting skills on the backyard green or relax on the upper, covered deck while enjoying peaks... View all property information
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    Chatham, Cape Cod 02669
    1 / 27
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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 / 16
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Spend your Cape Cod vacation in this well cared for 4 bedroom, 2 bathroom South Chatham rental home only 2/10ths of a mile to Pleasant Street Beach on Nantucket Sound. Forest Beach is only 3/10ths of a mile away as well. The screened in porch overlooking the woods is peaceful and spacious. Perfect... View all property information
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    Chatham, Cape Cod 02659
    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
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    South Chatham, Chatham 02695
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Fantastic views of Nantucket Sound abound from this updated 3 bedroom, 2 bath Chatham vacation rental only 1/10th of a mile from Ridgevale beach. No need to drive your car to the beach and pay to park, just throw your towel over your shoulder and walk down to the beach. The large furnished deck is... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Charming 1 floor cottage with 3 bedrooms and 1 full bath and peeks of Nantucket Sound. There is a large backyard and the beach is less than 500 feet away. Amenities include washer, dryer, dishwasher, cable TV (includes sports and weather) with DVD, Wi-Fi, enclosed outdoor shower, a deck and... View all property information
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    Chatham, Cape Cod 02659
    1 / 16
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    Situated at the end of a cul-de-sac in a wonderful neighborhood this Chatham home has a very private backyard which abuts conservation land. This 4 bedroom, 2 bath home is also just a half-mile from Nantucket Sound Beaches. Amenities include central AC, washer, dryer, dishwasher, cable TV (includes... View all property information
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    Chatham, Cape Cod 02659
    1 / 11
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 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 / 5
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located in the heart of Chatham Village, this award-winning home has been completely renovated and designed to capture the true spirit of the Cape. It has maintained its historic feel without compromising the modern comforts. The first floor offers a living room, dining room, sunroom,... View all property information
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    Chatham, Cape Cod 02633
    1 / 19
    3 Bedrooms, 4 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
    $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