Windsor Vacation Rentals

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Vacation Rentals in Windsor

Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1714)
"Nice place. Pleasantly surprised how big the suite was. The whole place was very clean from the suite itself, the huge indoor pool and hot tub. The clerk that checked us in was very knowledgeable of the area and just a pleasant person. She is an older lady, I forget her name but she is a definite asset to this property! On the down side the path to the main office was not well lit but we used our flashlights. Also there isn't restaurants on site or groceries available. We had to travel 25...
The price is CA $229
CA $265 total
includes taxes & fees
Sep 24 - Sep 25
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (897)
"Was good everything "
The price is CA $188
CA $207 total
includes taxes & fees
Oct 22 - Oct 23
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (9)
"Near Jacob's Pillow!"
Pristine Home In Becket Woods
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (205)
"My stay was shorter than I had planned but the few days I was here was so relaxing. First of all, the bed is so comfortable, I slept like a baby. Very quiet area. Nice to walk around with my dogs and explore. The cottage was nicely outfitted with any needs you might have. Beautiful time of year to stay here! I cannot wait to go back. I also want to say I appreciate that they allowed my two dogs. My dogs are very well behaved, and I travel with them quite often. Not all places allow this, so I...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Peace and quiet on the lake
9.6 out of 10, Exceptional, (190)
"Loved it!"
Peace and quiet on the lake
Cozy apartment located in quiet Williamsburg
9.6 out of 10, Exceptional, (41)
"Property was as advertised. Easy to get in and was exactly what we were looking for. "
The price is CA $204
CA $351 total
includes taxes & fees
Sep 24 - Sep 25
Cozy apartment located in quiet Williamsburg
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (35)
"We read all reviews before we booked and everything said was absolutely accurate. We had a perfect get-away, walking into a beautifully designed and appointed space. Chris is a super host, readily available and responsive to all question and offering fantastic advice on local offerings. Our days started with the best breakfast sandwich ever at his country store, the days ended with extraordinary sunsets and sitting in the hot tub looking at the endless stars. We brought our couch potato dog and...
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (213)
"We had a great stay at the carriage house! The property was incredible, we especially loved the variety of trails to explore. Our hosts were very helpful with directions and local recommendations. The house was charming and cozy. Would visit again! "
Berkshire Village Carriage House - Super Private!!
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (122)
"My partner and I were in MA to drop our eldest at Smith College for their first year. We chose Flight's End for the location and the fact that we were allowed to bring our pups with us. It was incredibly peaceful and just what we needed during an otherwise emotional time with such a big transition for our family. "
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (8)
"This is my second summer renting this house. It's great. Beautiful home, lots of light, in the woods, very comfortable. Our first year we had a rainy Sunday and it was fun to just hang out in. Very clean. The rental contact person was very responsive to a question we had. Five minutes from Jacob's Pillow. Lenox/Lee/Stockbridge are all just a quick drive away. Very quiet rural setting. A deer visited us this year, early on Sunday morning. Love this place."
Berkshires Cabin 2 Mi to Appalachian Trail!
Bear Creek Cabin
10.0 out of 10, Exceptional, (18)
"Great cabin, modern, clean, and comfortable."
The price is CA $543
CA $817 total
includes taxes & fees
Sep 24 - Sep 25
Bear Creek Cabin
Berkshire Lake access
10.0 out of 10, Exceptional, (46)
"Our stay was fabulous. The house was beautiful and well maintained and equipped. Joni was easy to work with and always available. "
Berkshire Lake access
Fox Hollow Luxury Ranch Laurel Lake
8.8 out of 10, Excellent, (16)
"Very quiet central location in the Berkshires. Close to all amenities. Enjoyed the lake canoeing and site seeing. Great house with everything needed. "
Fox Hollow Luxury Ranch Laurel Lake
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (39)
"My friends and I book this mansion for our annual getaway and it has become so dear to us. "
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (19)
"The house is lovely and so perfectly located. The two bedrooms were sufficiently apart and next to their own bathrooms so both couples had privacy.the screened in porch was perfect to hang out and play cards at night and my dog absolutely loved the back yard. The location is superb, conviently located central to Stockbridge, ,lenox and Great Barrington. Fifteen minutes to Tanglewood and the Norman Rockwell museums. There are so many hiking trails with fabulous mountain views nearby."
Stockbridge Home, Come Experience The Berkshires!
Quintessential 6-BR Berkshires Lodge
9.8 out of 10, Exceptional, (7)
"Nice. Quiet. The new pool is very nice."
Quintessential 6-BR Berkshires Lodge
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (16)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
Chic Pittsfield Home With A View!
9.2 out of 10, Wonderful, (5)
"We enjoyed our week in Pittsfield and at this home. The house was as described and expected, and it offered the privacy and seclusion we wanted. At the same time, the house is very conveniently located, and activities, beautiful walking trails, and restaurant options were nearby. We very much appreciated the reliable WiFi as some of our party had to work remotely during the week. Also, our pup loved the fenced in yard, the deck is great, and we enjoyed use of the fire pit. Would return again if...
Chic Pittsfield Home With A View!
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Other types of properties in Windsor you may be interested in

Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (396)
"Outdoor patio is nice. Surrounding area is beautiful. Things to see and do along with several restaurants and cafes."
The price is CA $172
CA $192 total
includes taxes & fees
Sep 24 - Sep 25
Life House Berkshires
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (989)
"Lovely old hotel with excellent bar and restaurant. Central to all Berkshire sights. Room clean and well-appointed; wonderful shower; lobby and many nooks in which to curl up with drink and a good book… Ambassador felines Jane and Jack make Red Lion Inn feel like home."
The price is CA $311
CA $408 total
includes taxes & fees
Oct 1 - Oct 2
The Red Lion Inn
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (1004)
"In addition to being reasonably priced, it was clean, quiet, and conveniently located. I loved the view of Main Street nestled against the hills. "
The price is CA $152
CA $169 total
includes taxes & fees
Sep 29 - Sep 30
Hotel Downstreet
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.

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, there are vacation rentals close to well known attractions in Windsor, or you can select a more secluded option if you'd like a relaxing place to stay. Windsor is known for its restaurants and shopping.

What are some of the best vacation home rentals in Windsor?

Peace and quiet on the lake: This vacation home rental near Windsor is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Savoy Mountain State Forest. Mount Greylock State Reservation Visitor Center and Mohawk Trail State Forest are a couple of places you'll find in the larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Windsor. Vacation rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family gatherings.