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Holiday villas in Windsor, MA

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Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 20 Rentals in the Windsor Area
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The following rentals are within 25 kilometers of Windsor, Massachusetts.

From
€93
Per Night
Hawley
3 Bedrooms, 2 Bathrooms, Sleeps 8
22 photos Details
Reviews (2) Make Enquiry
5 of 5 stars Reviewed 17 July 2014
I traveled with my husband, our 2 1/2 year old daughter, and four of our friends from New Jersey and Sweden who were visiting us. It was a great place to spend a couple days...
5 of 5 stars Reviewed 8 June 2014
Such a sweet little home. Tucked away but easy drive to so many sights and activities. We loved the decor, the gardens around the home, the pond across the street. Great...
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From
€93
Per Night
Becket
2 Bedrooms, 1 Bathroom, Sleeps 4
13 photos Details
Reviews (7) Make Enquiry
5 of 5 stars Reviewed 29 June 2014
The Becket cabin is a great getaway for young families. Our 4- and 2-year-old happily played about in and around the cabin and we spent a lot of time building fires in the fire...
5 of 5 stars Reviewed 24 October 2013
Cabin was outfitted nicely for the most part and in a great location.There was almost everything you could possibly need, especially kitchen supplies. Easy walk down to the lake...
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From
€158
Per Night
Plainfield
3 Bedrooms, 2 Bathrooms, Sleeps 10
23 photos Details
Reviews (13) Make Enquiry
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...
5 of 5 stars Reviewed 8 August 2013
Beautiful modern house with a nice charm. Very well kept, the property manager (Perry) was great to work with and ensure our stay was a joy. The property is fantastic, very...
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From
€115
Per Night
Lanesboro
2 Bedrooms, 1 Bathroom, Sleeps 4
10 photos Details
Reviews (12) Make Enquiry
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 30 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
€964
Per Week
Becket
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (9) Make Enquiry
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
€149
Per Night
Cheshire
2 Bedrooms, 1 Bathroom, Sleeps 5
19 photos Details
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From
€101
Per Night
Becket
2 Bedrooms, 2 Bathrooms, Sleeps 4
6 photos Details
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From
€782
Per Week
Becket
3 Bedrooms, 1 Bathroom, Sleeps 5
9 photos Details
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From
€112
Per Night
Dalton
5 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details
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From
€186
Per Night
Cummington
2 Bedrooms, 1 Bathroom, Sleeps 1
6 photos Details
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From
€127
Per Night
Pittsfield
3 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
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From
€261
Per Night
Becket
3 Bedrooms, 2 Bathrooms, Sleeps 5
16 photos Details
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From
€372
Per Night
Hinsdale
4 Bedrooms, 3 Bathrooms, Sleeps 8
18 photos Details
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From
€205
Per Night
Becket
4 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details
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From
€149
Per Night
Becket
3 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
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From
€97
Per Night
Pittsfield
3 Bedrooms, 1 Bathroom, Sleeps 8
20 photos Details
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From
€112
Per Night
New Ashford
4 Bedrooms, 3 Bathrooms, Sleeps 7
10 photos Details
Reviews (9) Make Enquiry
4 of 5 stars Reviewed 25 July 2014
When we first arrived, we were a bit skeptical, as the house was slightly more rustic than we had envisioned, but we quickly "moved in" and then it started to feel homey to us...
1 of 5 stars Reviewed 8 July 2014
Please note that 6 of 6 reviews I have written prior to this one have been very positive reviews. See my profile (http://www.tripadvisor.com/members/kayearth#CITY_TILES). The...
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From
€74
Per Night
Pittsfield
1 Bedroom, 1 Bathroom, Sleeps 5
8 photos Details
Reviews (1) Make Enquiry
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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
€223
Per Night
Becket
3 Bedrooms, 4 Bathrooms, Sleeps 6
17 photos Details
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From
€322
Per Night
Charlemont
5 Bedrooms, 3 Bathrooms, Sleeps 14
8 photos Details
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Suitability

  • Wheelchair access (3)
  • Elder access (9)
  • Suitable for children (18)
  • Pet friendly (7)
  • Smoking allowed (1)

Amenities

  • Other outdoor space (14)
  • Parking (14)
  • Grill (12)
  • Internet (12)
  • Washer/Dryer (11)
  • View all amenities
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