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Holiday Rentals in Chatham, MA

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    €850
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    1 / 12
    5 of 5 stars (2) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 10
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    €557
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    1 / 14
    5 of 5 stars (2) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 8
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    €557
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    1 / 13
    5 of 5 stars (4) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 8
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    €1,022
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    1 / 28
    5 of 5 stars (2) Excellent
    4 Bedrooms / 6 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
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    • Suitable for children
    • ?
    • x
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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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    5 of 5 stars Reviewed 17 October 2014
    The house was incredible. I have rented homes across the world with our family, and we are extremely picky in terms of 1. Cleanliness 2. renovation/newness 3. Location 4. Details...
    5 of 5 stars Reviewed 17 July 2014
    The units we rented at Oyster Pond exceeded our expectations. These two units (31 & 32) were very well appointed with TVs in every room, modern appliances, comfortable furniture...
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    €255
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    1 / 33
    5 of 5 stars (6) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
    About this property
    Completely renovated, this year round quaint Cape Cod open concept 1500 sq ft home has 3 bedrooms, 2 baths with a large two level outdoor deck overlooking beautifully landscaped yard. Sleeps 6-8 comfortably. Up to 10 including a pullout sleeper sofa. All rooms are bright and nicely appointed with... View all property information
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    5 of 5 stars Reviewed 22 August 2014
    Exceptional accommodations complete with high end cookware , grill, 22 ft cu refer, and all other needed appointments . Well located for excursions to the Fish Pier; shops...
    5 of 5 stars Reviewed 21 August 2014
    Planning a visit to Cape Cod from the UK was always going to be tough when you weren't sure how best you might get around or where was best to stay. We couldn't have got it more...
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    €241
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    1 / 20
    5 of 5 stars (4) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    This fully air conditioned 4 bedroom, 3 bath house on 1/2 acre lot sleeps 8 with 2 master suites! The main house has 3 bedrooms. One with a queen, one with 2 twins and one master suite with a queen. The 2nd master suite is located in a separate attached portion of the house with separate entrance.... View all property information
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    5 of 5 stars Reviewed 16 October 2014
    Stayed for a week in Oct and enjoyed every minute. Firstly, we booked the house at the very very last minute and the owners could not have been more obliging. They made their home...
    5 of 5 stars Reviewed 23 July 2014
    Perfect location to everything you could possible want to do. This rental makes you feel at home yet on vacation! Very spacious with everything you could possibly need. We loved...
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    €116
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    1 / 20
    5 of 5 stars (4) Excellent
    5 Bedrooms / 2 Bathrooms / Sleeps 9
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    ------------------------------------------------------------------------------------------------------ Like new 5 bedroom luxury Chatham vacation home on over 1 acre. Walk to Schoolhouse pond, clean freshwater pond with beach. Near the Cape Cod paved bike path and also only a few blocks to nice... View all property information
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    5 of 5 stars Reviewed 23 March 2013
    A group of friends stayed for a weekend reteat - and were so pleased with all the amenities of a fully equipped house and all the comforts of home, while staying on the cape...
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    €279
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    1 / 10
    2 of 5 stars (1) Poor
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Beautiful, Spacious, and Very Clean 3 bedroom 2 full bath home. Sleeps 8! Master suite with king size bed and private full bath. Large family room with entertainment system. Fully equipped kitchen with walk out deck. Private backyard with outdoor shower. One mile to ocean. Private pond... View all property information
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    2 of 5 stars Reviewed 3 July 2014
    * We have used Trip Advisor for several rentals and this one is best described as below average. Our extended family of 6 (4 adults, two kids) stayed in Beach Plum for 5 nights...
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    €325
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    1 / 6
    1 Bedroom / 1 Bathroom / Sleeps 3
    traveller have booked this property
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    • Dishwasher
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This stunning 1 bedroom cottage is located right on the beach in Chatham, the best of Cape Cod. Perfect for a relaxing getaway, this cottage is steps from the sand, and is ready for your vacation! Amenities: Television, Cable, Wireless Internet, Full Kitchen with dishwasher, microwave, coffee... View all property information
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    €557
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    1 / 18
    South Chatham
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Fabulous views of Nantucket sound are the focus of this newer home. Built in 2000, it sits at the end of a quiet dead end street overlooking an amazing view of nature, ocean and sky. From every window see Nantucket Sound, Hardings Beach and Stage Harbor Lighthouse. The house has an open floor... View all property information
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    €279
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    1 / 10
    5 Bedrooms / 3 Bathrooms / Sleeps 11
    traveller have booked this property
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Wonderful, family-friendly, 5- bedroom house close to town. One ground-floor bed/bath. Fenced-in, flower filled, back yard with outdoor shower, grille, table and chairs, deck/patio. Walking distance to town or take extra bikes to ride to Lighthouse Beach/ Oyster Pond. Kitchen table has room for... View all property information
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    €226
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    1 / 11
    South Chatham
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Recently renovated cottage in sought after Cockle Cove beach neighborhood. Walk or bike 4/10ths mile to warm, sandy & family friendly town beach on Nantucket Sound. Direct waterfront location on tidal Taylors Pond, with stunning views and access to owner's private dock for kayaking & boating into... View all property information
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    €2,786
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    1 / 20
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Our Five bedroom Chatham vacation home is located on a quiet side street, yet near town. The five large bedrooms are added to by a den with double pull-out and a basement/play area with 2nd pull-out making it perfect for family groups, weddings, or reunions. We have 1 king bed, two queen beds, one... View all property information
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    €604
    / Night
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    1 / 9
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Sit on the porch in one of the rockers and enjoy your morning coffee or afternoon beverage of choice and watch the world go by. As soon as you drive in the driveway and smell the salt air, you start to relax and feel the welcoming embrace of this historical in town main house and cottage. With five... View all property information
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    €81
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    1 / 9
    South Chatham
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for... View all property information
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    €464
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    1 / 7
    2 Bedrooms / 1 Bathroom / Sleeps 3
    traveller have booked this property
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    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This stunning 2 bedroom cottage is located right on the beach in Chatham, the best of Cape Cod. Perfect for a relaxing getaway, this cottage is steps from the sand, and is ready for your vacation! Amenities: Television, Cable, Wireless Internet, Full Kitchen with dishwasher, microwave, coffee... View all property information
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    €604
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    1 / 6
    3 Bedrooms / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This stunning 3 bedroom cottage is located right on the beach in Chatham, the best of Cape Cod. Perfect for a relaxing getaway, this cottage is steps away from the sand, and is ready for your vacation! Amenities: Television, Cable, Wireless Internet, Full Kitchen with dishwasher, microwave,... View all property information
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    €106
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    1 / 21
    South Chatham
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Enjoy this adorable, classic 2 bedroom and 1 full bath Cape beach cottage only a 10 minute walk to Nantucket Sound beaches. Amenities include dishwasher, washer/dryer, one window air conditioning unit, cable TV (with basic cable) with VCR & DVD, microwave, board games, children’s books and videos,... View all property information
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    €293
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    1 / 14
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    traveller have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    4 bedroom house with 2 master suites. Perfect for extended family and friends. Close to town and beaches. View all property information
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    €88
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    1 / 11
    4.5 of 5 stars (10) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    At this quiet lakeside cottage you can experience classic Cape Cod with all the modern amenities. Enjoy beautiful sunsets as well as swimming and canoeing at the lake---and only be a short trip to the beach or Chatham center. The cottage features cathedral ceilings, a fireplace in the living... View all property information
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    5 of 5 stars Reviewed 27 August 2014
    The property consisted of three beds (2 futon and 1 queen size bed) which was perfect for my three person family. The cottage was only a few minutes from two great beaches nearby...
    4 of 5 stars Reviewed 15 September 2013
    Our favorite thing was sitting with coffee in the am, or a beer for sunset, down at the small beach area on the lake. Solitude and scenery. Maybe 3 other cottages were occupied...
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    €305
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    1 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Cape Cod Dreaming by the Beach - Perfect for families to share! Relax by escaping to our newly refurbished and decorated classic Cape Cod cottage, just a short walk, 4/10 of a mile, to sandy Pleasant Street Beach on Nantucket Sound. It is walkable to Forest Street and Red River Beaches. Swim,... View all property information
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    €93
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    1 / 15
    5 of 5 stars (6) Excellent
    South Chatham
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Grill
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This immaculate two-bedroom/one-bath cottage sleeps five and is cozy and affordable. It's located one-half mile from Cockle Cove Beach on warm Nantucket Sound. Situated on a quiet cul de sac with a nearby childrens playground, this property is protected and cooled by pine trees and salty breezes.... View all property information
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    4 of 5 stars Reviewed 2 September 2014
    We loved being so close to Cockle Cove Beach. The outside shower was a hit, too. My two teenaged boys loved, loved, loved this place. It would be even better if it had wifi.
    5 of 5 stars Reviewed 26 August 2014
    I was so happy with our stay! the cottage was very cute and was just enough room! it was close to just about anything you can want to do in the cape. the welcome gift was very...
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    €916
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    1 / 22
    5 of 5 stars (11) Excellent
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Located on a bluff overlooking Nantucket Sound just a 4 minute walk from Chatham's Hardings Beach, this luxurious home can accommodate an extended family of 10. There are two master suites with Queen beds and private bath (0ne with jacuzzi tub) and three twin bedded rooms - a total of 5 bedrooms... View all property information
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    5 of 5 stars Reviewed 18 December 2014
    We had a wonderful stay during our time here in Cape Cod. The owners could not have been more delightful and the house was absolutely fantastic. It was a five minute walk to the...
    5 of 5 stars Reviewed 24 July 2014
    This was our 5th year at this house. We have enjoyed our stay every time! The house was very clean (much more than my own house is, I'm sure) and the artwork and decor was...
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    €269
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    1 / 15
    4 of 5 stars (3) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Ocean Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    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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    4 of 5 stars Reviewed 2 November 2012
    Our family spent Columbus Day weekend at this property located within walking distance of two beaches and enjoyed it very much. The expanded Cape had comfortable room for eight of...
    3 of 5 stars Reviewed 3 July 2012
    I traveled with three friends to Cape Cod for a week. Two of us were pretty happy with the selected property, and the other two were a little disappointed. The house is located...
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    €1,300
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    1 / 11
    3 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Adorable, cozy, renovated home - new to rental market. Air conditioned for comfort and WIFI for staying connected.Equipped with blu-Ray DVD, Dish TV with Blockbuster for streamed movies. Enjoy our gourmet kitchen with stainless steel appliances, a beautiful sunny living/dining area, deck and... View all property information
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    €172
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    1 / 9
    4 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This newly renovated house overlooks White Pond in Chatham and consists of 4 bedrooms and two full bathrooms. Located on the first floor is the master bedroom with king size bed, bathroom with washer/dryer, full kitchen, living room with cable television, enclosed sun porch, and screened porch. The... View all property information
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    €163
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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    About this property
    Our Cranberry Way home is a charming 2 bedroom, 2 bath (one new) year-round home which is located at 47 Cranberry Way in South Chatham and it can comfortably accommodate up to 6 people. It is only 0.6/mi. to Nantucket Sound, the warm water side of Cape Cod! It is a pet-friendly home (with an... View all property information
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