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Holiday Rentals in Windsor, MA

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All 25 Rentals in the Windsor Area
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From
₹10,777
Per Night
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1 / 12
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Windsor
2 Bedrooms, 1 Bathroom, Sleeps 6
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The following rentals are within 25 kilometres of Windsor, Massachusetts.

From
₹6,096
Per Night
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1 / 13
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Becket
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (8) Make Enquiry
From
₹9,237
Per Night
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1 / 20
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Pittsfield
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
From
₹79,746
Per Week
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1 / 16
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Becket
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (9) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Pretty cottage in the woods on a beautiful private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe or fish from the back yard, or just lounge... View all property information
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5 of 5 stars Reviewed 17 January 2014
We had a wonderful time in the Berkshires, and this cottage was the central part of our weekend. The house was superb and extra clean, with everything provided. Views were...
5 of 5 stars Reviewed 2 October 2013
Excellent spot for a quiet retreat. Located on a nice pond with just a few neighbors we never even saw or heard. The cottage has all the essentials. Very clean and inviting...
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From
₹10,777
Per Night
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1 / 10
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Lanesboro
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (12) Make Enquiry
Amenities & Details
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. It is perfect for romantic weekends or family... View all property information
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5 of 5 stars Reviewed 8 July 2014
We were lucky to happen upon this gem, and highly recommend it to families visiting the area of Mt. Greylock. Great on a rainy day, and interesting for all given the history of...
5 of 5 stars Reviewed 31 May 2014
We have stayed in several vacation rentals, and this one was extremely charming. The very first time I saw this one I just knew we had to vacation here while we were in The...
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From
₹12,008
Per Night
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1 / 12
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New Ashford
4 Bedrooms, 3 Bathrooms, Sleeps 7
Details Reviews (15) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Housekeeping...
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
The Berkshire Gorge House sits beside the Green River above a turbulent set of cascades, on the western slopes of Mt. Greylock. This 5-bedroom house was built in 1910 by New England’s finest craftsmen. It has been recently remodeled and is offered for rent. The house offers a new kitchen with gas... View all property information
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5 of 5 stars Reviewed 4 January 2015
I am kicking myself that I didn't invite my brother, sister-in-law and their small kids to come with us on this trip. There sure was plenty of room! Right when you enter the...
5 of 5 stars Reviewed 1 December 2014
The house was everything we expected. Right from the beginning there was clear communication between us, the owner and the property manager. The booking process was easy. Checking...
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From
₹13,055
Per Night
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1 / 23
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Plainfield
3 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
Details Reviews (16) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Housekeeping...
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Experience a Berkshire get-away in this huge secluded luxury modern house. It's the only house that is surrounded by 10,000 Acres of protected Hawley State forest. Escape from headaches and the rat race. No cell phone reception here! But we have WiFi and a house phone. We like to define our country... View all property information
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3 of 5 stars Reviewed 25 August 2014
The home and grounds were lovely but need some updating,and a good cleaning. Location was secluded with plenty of forest and hiking trails, and a scenic lake for fishing. The...
5 of 5 stars Reviewed 29 May 2014
We all thoroughly enjoyed our long weekend at this lovely house. It was spacious, well situated, and well equipped. We were sorry our stay was so short, and the time in the...
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From
₹7,082
Per Night
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1 / 35
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Charlemont
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (101) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B’s. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening... View all property information
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5 of 5 stars Reviewed 31 December 2014
My mother, my dog and I spent the weekend following Christmas at the Cavalier Cottage. We all had an amazing time. The B&B is located close to a few state parks, hiking, and a...
5 of 5 stars Reviewed 27 November 2014
Cavalier Cottage is a gem for people and dogs. My family and I were impressed by the amount of detail put into it---- it had everything you can think of- gourmet tea and...
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From
₹16,935
Per Night
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1 / 32
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Becket
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our... View all property information
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5 of 5 stars Reviewed 30 August 2014
This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents...
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From
₹6,158
Per Night
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1 / 8
Pittsfield
1 Bedroom, 1 Bathroom, Sleeps 5
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Indoor Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances,... View all property information
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5 of 5 stars Reviewed 3 July 2013
WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern...
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From
₹9,237
Per Night
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1 / 13
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Florida
1 Bedroom, 1 Bathroom, Sleeps 5
Details Reviews (2) Make Enquiry
Amenities & Details
  • Grill
  • Gym
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
50 acre mountain top property in the Berkshires located between North Adams and Charlemont, Massachusetts with mountain views and within close proximity to all kinds of outdoor recreational opportunities including beaches, swimming, whitewater rafting and kayaking, hunting and fishing, hiking and... View all property information
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5 of 5 stars Reviewed 2 July 2014
Great apartment (one floor of a cabin) to rent. Stayed very cool and comfortable and had comfortable rooms. Bathroom was quite big and was stocked with more than enough...
5 of 5 stars Reviewed 2 November 2013
What could be better than a private apartment on top of a mountain in the fall in western Massachusetts with french doors open to the sunrise? Margot is a most gracious and...
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From
₹8,313
Per Night
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1 / 22
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Hawley
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
3 Bedroom house, know as Flight's End, is for rent by day, weekend, week or month. Great for romantic get away or a family outdoor vacation. Not a party house. Fifteen minutes to Charlemont, Ashfield and Shelburne Falls. House is located on a brook and across the road from a private pond (not... View all property information
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5 of 5 stars Reviewed 12 September 2014
The house was very clean and cozy. Everything was as shown in the pictures. As my friends and I are from the city, we love how quiet the area is. BBQ grill and bonfire were the...
5 of 5 stars Reviewed 21 August 2014
Found this property to be a good one for the three of us. Great price, owner nearby and accessible. Very clean and comfy. Would have appreciated a little more about directions to...
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From
₹18,474
Per Night
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1 / 12
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Washington
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Shingle style, timber frame, passive solar, Berkshie 'Cottage' Built along side of Coles Brook, the manor is a retreat destination any time of the year. The seclusion and tranquility of the custom built home and site are unique and comforting for family gatherings and weekend getaways. View all property information
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From
₹30,790
Per Night
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1 / 18
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Hinsdale
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the... View all property information
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From
₹9,237
Per Night
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1 / 6
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Savoy
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and... View all property information
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From
₹9,237
Per Night
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1 / 15
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Dalton
5 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Cottage at Holiday Farm is a gorgeous place to spend the month, week or a mini-break weekend. Centered in the heart of a real, working farm there are miles of wooded trails and farm roads right outside the door. You can wander the farm, enjoy seasonal sports activities from cross-country skiing... View all property information
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From
₹12,316
Per Night
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1 / 19
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Cheshire
2 Bedrooms, 1 Bathroom, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Internet Access
  • Mountain Views
  • Ping Pong Table
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Comfortable house situated on the shore of Hoosac Lake with beautiful, long views stretching across the large lake. It's fully furnished, with cable TV, stereo, and high-speed Internet. There's a big kitchen, with a central island for dining. The expansive living/dining room and attached study,... View all property information
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From
₹8,005
Per Night
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1 / 11
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Hinsdale
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Internet Access
  • Safe
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large... View all property information
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From
₹26,603
Per Night
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1 / 8
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Charlemont
5 Bedrooms, 3 Bathrooms, Sleeps 14
Bookings
Details Make Enquiry
Amenities & Details
  • Grill
  • Internet Access
  • Mountain Views
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski... View all property information
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From
₹64,659
Per Week
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1 / 9
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Becket
3 Bedrooms, 1 Bathroom, Sleeps 5
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
You can 'have it all' in the Berkshires! Our cozy contemporary home is less than 30 minutes from all Berkshire cultural and historical attractions, but tucked away in woodsy peace and privacy. Our four acres look out over a large lawn, lovely flower and herb garden, old apple orchard, and trout... View all property information
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From
₹31,406
Per Night
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1 / 27
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Williamsburg
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Internet Access
  • Mountain Views
  • Safe
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Flower Hill Farm Retreat is housed within a 1790 farmhouse and studio situated on an east facing hillside fifteen minutes west of Northampton, Massachusetts. You can rent the entire retreat or separate apartments. See Rates below in this write up. Rambling organic gardens, fields and forest... View all property information
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From
₹9,237
Per Night
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1 / 6
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Becket
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water... View all property information
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From
₹18,474
Per Night
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1 / 16
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Becket
3 Bedrooms, 4 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional... View all property information
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From
₹101,607
Per Week
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1 / 10
Becket
6 Bedrooms, 3 Bathrooms, Sleeps 11
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs and birds.... View all property information
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From
₹21,553
Per Night
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1 / 16
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Becket
3 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Private Fishing...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Lovey 3 Bedroom house on 200 acres in the Beautiful Berkshires. Drive in, close the gate and enjoy the privacy, sunny lawn leading to a small private lake for swimming, canoeing, fishing. Fully furnished and stocked with everything you need for a stay with family or friends. New bathrooms and... View all property information
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