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Compare 221 Vacation Homes in Windsor with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is AED 551
AED 837 total
includes taxes & fees
7 Mar - 8 Mar
Berkshire Village Carriage House - Super Private!!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (210)
"This was a cozy tucked away location that seemed far away from everything which was exactly what we wanted. The host was extremely communicative before and during the stay. The house had fresh linens and towels as well as basic cleaning supplies. It was cozy for a wintery weekend in. We enjoyed snowshoeing on the frozen lake! Pet-friendly was a huge plus! "
Peace and quiet on the lake

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is AED 2,196
AED 3,898 total
includes taxes & fees
11 Mar - 12 Mar
Hancock Village Inn at Jiminy Peak

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (119)
"The property was great for our group of 8. Slept everyone comfortably, with plenty of places to hangout and lounge all together. We had planned to cook in for a couple meals, so it was a hugely pleasant surprise to see that the kitchen was stocked with every cooking utensil, serving dish, and glassware that you could possibly need. We were maybe even more prepared than in my own kitchen at home. Also very well located. Had an excellent stay and would come back!"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

9.6 out of 10, Exceptional, (29)
"We had a wonderful stay here in Pownal!! We came for a writing retreat, looking for a cozy property with space to think, work, catch up, and relax. Talk about inspiring surroundings!! The property is cozy and well kept, with a spacious kitchen and plenty of little luxuries! Warm floors in the bathroom and a hot tub, fireplace… it’s a perfect spot. The property manager was communicative and friendly. Highly recommended! "
Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (67)
"Tom’s cottage was the perfect place for us to stay to enjoy the new year in quiet Lenox. It was centrally located which made exploring town easy and convenient. The check in and out process was super simple and Tom made himself easily accessible throughout the stay. "
Heart of Lenox Walk to Town Cozy Cottage!

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat

Comfortable Berkshires retreat on mtn resort, SISO

The price is AED 591
AED 1,768 total
includes taxes & fees
2 Apr - 3 Apr
Comfortable Berkshires retreat on mtn resort, SISO

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (32)
"The house was nicer than we expected we had a wonderful time and will recommend to friends."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (6)
"I booked the weekend for my girlfriends birthday with a couple of her friends. The game room was a massive hit as was the propane fireplace outside. We also enjoyed watching the snow fall on the frozen lake. William was very responsive to messages and calls. We enjoyed our stay immensely and are hoping to come back in the summer"
Berkshires Lakefront Retreat

Lee Manor Berkshire House for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.

10.0 out of 10, Exceptional, (9)
"Our family of six stayed at Lee Manor during the Christmas holidays. The house was a lovely older home with modern amenities. It was very well stocked with all the needs of home. The house was spacious and the beds were very comfortable. We enjoyed the back sitting area with the stove heater for watching movies, playing games in the front room, and gathering in the kitchen for snacking. We had great communication with the owners and the Check-in and Check-out process was flawless. It was a...
Lee Manor Berkshire House for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (71)
"Very spacious and comfortable. Biggest selling point was its proximity to family in the area."
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (85)
"This old barn was renovated into a great place to stay. Jane and Ian paid careful attention to details, light, colors, materials. Very comfortable and relaxing. The setting is gorgeous, and the sheep are fun. (FYI: It may be helpful to understand the layout and bathrooms: the new bathroom is at the far end of the smaller bedroom. This works great for a couple to have their own bathroom. The other bathroom is within the larger bedroom with the bunk bed, but in an area close to the door,...
19th c. Barn in the Berkshires

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (40)
"We have stayed here twice and it is a great spot, located a few minute drive north of downtown Lenox. The house is cozy yet spacious and is great for our family to stay in while visiting family in the area. We used the kitchen to cook a meal during one of the stays and we had everything we needed. There is an air hockey table in the basement which the kids enjoyed. The house is on a main road, but it was still easy enough to pull in and out of and the noise of the road did not bother us at all....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

10.0 out of 10, Exceptional, (4)
"We had a great weekend stay here with our dog. He loved the backyard and felt right at home. Everything was clean and great location."
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Massachusetts Vacation Rental w/ Deck & Grill

9.2 out of 10, Wonderful, (14)
"There’s a backup generator if you lose power!! Great log cabin feel and plenty of space. "
Massachusetts Vacation Rental w/ Deck & Grill

Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!

9.8 out of 10, Exceptional, (20)
"The home was modern, clean and efficient space for the 6 of us. The interior is actually a bit brighter than the pictures would suggest. Kitchen was well stocked. The loft had a TV room, plenty of DVDs and games, and an extra Twin Bed. Beds in general were comfortable and the sheets and comforters were modern.We were there during a heavy snowstorm and Venetia and her family were prompt and very responsive with our questions. They went over and beyond in helping us with one of our cars that...
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!

Dancing Horse Lodge

9.4 out of 10, Exceptional, (39)
"Very cozy property in a nice secluded location. "
Dancing Horse Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Windsor

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1784)
"Awesome place extremely close to the ski mnt. Has an inside / outside pool plus hot tub! Rooms were great"
The price is AED 400
AED 476 total
includes taxes & fees
10 Mar - 11 Mar
Vacation Village in the Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 547
AED 600 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.