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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.
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    From
    €4,710
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    1 / 11
    4 Bedrooms / 5 Bathrooms / Sleeps 11
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    €897
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    €2,467
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    6 Bedrooms / 2 Bathrooms / Sleeps 11
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    €3,589
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    1 / 15
    North Chatham
    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    2015 Rental Rate ~ $6300 per week, including the cleaning fee and the linens and bath towels Off Season ~ $4300 per week including the cleaning fee and the linens and bath towels Gorgeous home conveniently located to everything Chatham has to offer! Beautiful upscale kitchen featuring all new,... View all property information
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    €3,028
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    1 / 17
    North Chatham
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Be one of the lucky ones to enjoy the picturesque waterviews and great location of this North Chatham rental property. Located on a quiet cul-de-sac with a path that leads down to the water (sorry no beach area!) with a lovely spacious yard and a picket fence covered with roses...a true Cape Cod... View all property information
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    €2,916
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    1 / 7
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    2015 Rental Rate: $4900 per week including the cleaning fee ~~ Off-Season Rate: $3450 per week including the cleaning fee Gorgeous home on Cross Street, a short walk to everything downtown Chatham has to offer! This lovely home with central air has everything you would want, plus a fabulous... View all property information
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    €1,705
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    1 / 12
    5 Bedrooms / 3 Bathrooms / Sleeps 9
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    About this property
    60 Hallet Lane - ID# 104906. In the heart of the Old Village Antique home in the heart of Old Chatham Village. Convenient to Lighthouse Beach, Village shops and restaurants. Five Bedroom, 3 Bath, 4/10 mile to Lighthouse Beach. $2500 per week in season with a $210 Cleaning Fee. Please view our... View all property information
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    €852
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    1 / 9
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Suitable for children
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    About this property
    2015 Rental Rate: $1050 per week, including the cleaning fee ~~Off Season: $750/wk, with cleaning fee Quaint 2 bedroom cottage surrounded by beautiful gardens! Sitting on .5 acre in lovely North Chatham, this private getaway is just what the doctor ordered. Living area and additional eating and... View all property information
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    €2,467
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    1 / 9
    6 Bedrooms / 2 Bathrooms / Sleeps 11
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    • Satellite TV
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    • Water Views
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    • Pets allowed
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    About this property
    2015 Rental Rate: $4525 per week including the cleaning fee ~~ Off-Season: $3025 per week including the cleaning fee ~Experience a true Old Cape Cod vacation in this rambling home located about 2/10 of a mile from a private beach at Stage Harbor. Great views from the 2nd story deck and wisteria... View all property information
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    €1,166
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    1 / 10
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    You'll be under 1/10th of a mile from Pleasant Street Beach at this cute two bedroom cottage. Amenities include cable TV (includes NESN, ESPN, Weather Channel, etc.) with DVD, WiFi, one window a/c unit in the living room, a deck with furniture and a gas grill, and an enclosed outdoor shower. This... View all property information
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    €1,436
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    1 / 12
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    COMFORT AND AFFORDABILITY! Reserve this three bedroom/2.5 bath rental and you will enjoy the true Summer feel of this house! Property is very light and bright, well maintained and nicely furnished. Offers central air conditioning, wireless internet, master bedroom with private bath and lower level... View all property information
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    €3,364
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    1 / 20
    5 Bedrooms / 5 Bathrooms / Sleeps 11
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    • Satellite TV
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    About this property
    2015 Rental Rate ~~ $5325 per week including cleaning Off Season $4,075 per week included cleaning Gorgeous, newer home located just a quick walk to Hardings Beach. All the upscale furnishings throughout this home are brand new for the 2012 season! Plenty of bedrooms for a large group, including a... View all property information
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    €1,256
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    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This Chatham rental home has 3 bedrooms and 1.5 baths. It's situated in a private setting, abutting conservation and convenient to both the town and the beach. This property is only 1/2 mile to White Pond which is great for fishing, swimming, paddleboarding, etc. The many amenities offered include:... View all property information
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    €1,884
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    1 / 9
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    WALK TO TOWN AND LIGHTHOUSE BEACH....LOCATED IN THE HEART OF THE OLD VILLAGE! this charming renovated antique home is just a short walk to Lighthouse Beach and to Town! The perfect location in Chatham! Central Air Conditioning, wireless interent access, comfortable interior with new living room... View all property information
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    €2,871
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    1 / 29
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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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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    €2,243
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    3 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Grill
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    • Satellite TV
    • Waterfront
    • Water Views
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    About this property
    2015 Rental Rate: $3675 per week, including the cleaning fee~~ Off-Season: $2675 per week, including the cleaning fee Unique Sea Captain's home with stunning waterfront views, right on the beach! Everyone's dream vacation spot in Chatham. Upscale furnishings throughout the home. Library stocked... View all property information
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    €1,480
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    4 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    2015 Rental Rate: $2495 per week including LINENS AND the cleaning fee ~~ Off-Season: $1895 per week including LINENS AND the cleaning fee Beautifully furnished home centrally located in Chatham. Just a quick drive to one of Chatham's many saltwater beaches or quaint village for shopping and... View all property information
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    €2,871
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    1 / 21
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
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    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
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    About this property
    Classic old-style Cape Cod home overlooking Chatham Harbor with private stairs leading down to Lighthouse Beach. SUNDAY arrival and departure this Classic old-style Cape Cod living in a simply spectacular location. This 4 bedroom home inside the Old Village Historic District overlooks gorgeous... View all property information
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    €1,615
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    1 / 7
    2 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    This condo is located on Starfish Lane. It is steps away from Little Beach and Outer Most Marina. There is a living room with skylights and catheral ceiling. Kitchen with breakfast bar, full bath and bedroom with twins. The second story is a loft area with a queen bed and twin and full bath.... View all property information
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    €269
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    1 / 19
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
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    About this property
    Pet Friendly! Classic Cape Cod Vacation Home Rental in Chatham near Schoolhouse Pond for freshwater swimming. It is located in a residential area and is convenient to the Cape Cod Bike trail, and the Chatham Airport and restaurant (Hanger B eatery). It has 3 a/c units and wifi too. Enter the front... View all property information
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    €435
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    1 / 18
    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Pets allowed
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    About this property
    Pet Friendly! Spend Lazy summer days at this Cape Cod Vacation rental in Chatham. 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 relaxing escape to the Cape. From kayaking (2 included!) to boating enthusiasts this rental... View all property information
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    €2,692
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    1 / 19
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    Lovely bright home with waterviews and central A/C in North Chatham Stunning, beautifully furnished and decorated home with central A/C and views of Pleasant Bay out to the Atlantic is located in a lovely area of North Chatham. This reverse floor plan home with the living areas on the second floor... View all property information
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    From
    €449
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    1 / 2
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    Chatham Village Classic, Behind Lighthouse $5,200 Prime Summer Weekly Rate This grand Chatham Village family home is located in Chatham, right near the Lighthouse.This vintage antique house has 5 bedrooms, and a premier village location.Walk 3-5 minutes down the road to Lighthouse Beach, or walk... View all property information
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    €1,346
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    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    2015 Rental Rate: $2375 per week including the cleaning fee ~~ Off-Season: $1675 per week including the cleaning fee Updated rental close to downtown Chatham and all it has to offer! Central Air Conditioning throughout! Walk down to the Chatham Playground or Chatham's A's baseball games too.... View all property information
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    €1,794
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    1 / 8
    North Chatham
    5 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Air Conditioning
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    About this property
    2015 Rental Rate: $3225 per week, with the cleaning fee ~~Off-Season: $2225 per week, with the cleaning fee~~ Spacious 5 bedroom on quiet cul-de-sac in prestigious North Chatham. Walk to beach, Band concerts, baseball games, Movies, and fish pier. House has just been completely renovated with... View all property information
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    €2,243
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    1 / 16
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Pets allowed
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    About this property
    Spend your vacation in this newer 2+ bedroom 2.5 bath Chatham rental home situated on a lovely country lane 3/10ths of a mile to Pleasant Street beach on Nantucket Sound. This home boasts nearly every possible amenity including central air, washer/dryer, dishwasher, cable TV (includes NESN) with... View all property information
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    €1,884
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    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    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 bath house. You can enjoy shopping, fine restaurants, band concerts, ball games and much, much more. Amenities include washer/dryer, dishwasher,... View all property information
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    €1,346
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    1 / 9
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Satellite TV
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    About this property
    2015 Rental Rate: $3000 per week, including the cleaning fee~~~~ Beautifully decorated home on quiet dead-end street. Open floor plan makes it light and bright! Large living room with additional den give you lots of lounging space while a quick walk into downtown will perk you right up. A private... View all property information
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    €718
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    1 / 7
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    2015 Rental Rate: $1500 per week, including the cleaning fee~~~NO OFF-SEASON~~~ Enjoy your Chatham summer vacation in this light and bright pet-friendly home on a quiet side street, on the way to Ridgevale Beach, one of Chatham's most popular family beaches! Filled with bright colors and comfy... View all property information
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    €628
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    1 / 10
    4 Bedrooms / 4 Bathrooms / Sleeps 11
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    • Air Conditioning
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    • Satellite TV
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    • Water Views
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    About this property
    Just Listed -- Immaculate Chatham Center Renovation. Walk to Beach & Village. $7500 Prime Summer Weekly Rate 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. The home... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    JUST STEPS TO OYSTER POND BOAT LAUNCH AND SHORT WALK TO OYSTER POND BEACH AREA!!! Just 4/10's mile to town and beach! Partial waterviews from the front porch with rocking chairs provided. Small deck off the back of the house with outdoor grill. Picnic table in the backyard area. Just around the... View all property information
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    €1,436
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    1 / 11
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    2015 Rental Rate: $2800 per week including the cleaning fee Off-Season Rate: $1800 per week including the cleaning fee You will love this 4 bedroom home near Ridgevale Beach! Located at the end of a dirt road with water views of a freshwater pond and surrounded by conservation land, it is quiet and... View all property information
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    €1,077
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    1 / 30
    North Chatham
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Comfortable three bedroom home located on a quiet side street! TWO PORTABLE AIR CONDITIONING UNITS HAVE BEEN ADDED TO THE PROPERTY!! (One unit in the master bedroom and one in the living/dining area. Nicely furnished, well maintained home with rear patio and nice yard area for sports and games.... View all property information
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    €2,064
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    4 Bedrooms / 2 Bathrooms / Sleeps 9
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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 three bedrooms and one full bath; the cottage has an open plan with kitchen and bedroom areas as well as a full bath. There's a good sized yard with a gas grill and... View all property information
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    €1,615
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • x
    • Wheelchair access
    • Elder access
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    About this property
    2015 Rental Rate: $2350 per week including the cleaning fee Off Season Rate: $1950 a week, including the cleaning fee 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... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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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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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
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    About this property
    2015 Rental Rates: $2475 per week, including the cleaning fee ~~ Off-Season: $1375 per week, including the cleaning fee Bright and cheerful summer cottage, walking distance to the warm waters of Hardings Beach! Located in Hardings Hills, there is also an association picnic table and dock - great... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Satellite TV
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    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • x
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    • Elder access
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    About this property
    2015 Rental Rate: $3200 per week, including the cleaning fee ~~~~~NO Off Season~~~~~ Terrific home on a quiet cul de sac with lots of room for everyone! Enjoy pretty views of Buck's Creek from many windows, and decks...including one on the second floor. Lovely, private outside patio and deck.... View all property information
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    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    455 Shore Road, Chatham - Property ID: 105467 Wonderful Captains House located on the highly desirable Shore Road in Chatham with water views of Chatham Harbor and walking distance to Claflin Landing Beach and Chatham Village! Wonderful Captains House located on the highly desirable Shore Road in... View all property information
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    €3,140
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    3 Bedrooms / 3 Bathrooms / Sleeps 9
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    About this property
    This is a lovely, recently renovated 3+ bedroom, 2 1/2 bath house within 2/10ths of a mile to popular Ridgevale Beach. There's lots of living space including two living areas, a den, as well as a sun room. Every room has been freshly painted and there's recently refinished hardwood floors... View all property information
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    5 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Suitable for children
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    About this property
    195 Cedar Street Chatham - ID# 106000 SPECIAL: Rent July 4-11 and get July 3 for the same rate. Come for the 4th. Location, location, location! Only a half mile to the beach at Oyster Pond and 3/4 mile to the Village of Chatham. Located on the Chatham Loop, a great walking/jogging/biking route.... View all property information
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    €1,436
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    2015 Rental Rate: $3175 per week including the cleaning fee Off-Season: $1775 per week, including the cleaning fee Walk to town in minutes from this recently updated ranch on Highland Avenue! Light and bright with new furnishings throughout, this adorable home features wireless internet, central... View all property information
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    6 Bedrooms / 2 Bathrooms / Sleeps 10
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    About this property
    OWNER WILL ALLOW TENANTS TO BRING A DOG!! Charming antique home which is just a 5 minute walk to Stage Harbor. Just around the corner from Stage Harbor Marina and Yacht Club. Expansive farmers porch off the back and very large front yard. Owner offers use of tennis court next door from 10 AM to 5... View all property information
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    3 Bedrooms / 4 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Beautifully updated ranch in Chatham Gorgeous fully renovated home in a quiet neighborhood. Open floor plan with a lovely kitchen featuring granite countertops. Central air conditioning, hardwood floors and wireless internet are just a few of the amenties for a comfortable vacation. Lovely... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    About this property
    ATTENTION ALL BEACH LOVERS!! Access across the street to right of way path that leads to the beach, just south of Lighthouse Beach. House is also within walking distance to Lighthouse Beach if you prefer! Partial views of the water from the second floor deck. Three air conditioning units in the... View all property information
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    South Chatham
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    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 2 a/c window units for the second floor bedroom, a dishwasher, washer/dryer, microwave, expanded cable TV (includes NESN, ESPN, Weather Channel,... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Suitable for children
    • ?
    • ?
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    • Elder access
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    About this property
    COZY AND COMFORTABLE!! This Chatham home has three bedrooms and two baths with central air conditioning, wireless internet, flat screen television, master bedroom with private bath. Enjoy peace and tranquility in this quiet residential neighborhood of Chatham. This home is centrally located and a... View all property information
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    €269
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Water Views
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Pet Friendly! Newer Cape Cod Vacation Rental Townhome with beautiful views of Perch Pond, just minutes to Chatham Village and Beaches. Luxury Rental includes: Central A/C, 3 levels of living space with flat screens on every level, granite counter tops and WIFI! Enter through the front door and to... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    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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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Grill
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    • Satellite TV
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    This Cape Cod Vacation Rental Home is located on a dead end street ,in a central Chatham location so you can walk to Oyster Pond , also into the downtown Village of Chatham and enjoy all that this seaside village has to offer. It has plenty of space for all to enjoy, Central A/C to keep you cool... View all property information
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