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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Windsor vacation homes

A wooden deck with two chairs and a table, overlooking a green landscape with a tree and hills.

1. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
Riverbend Berkshire East Basecamp - 3 bedrooms available
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

2. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is CA $73
CA $401 total
includes taxes & fees
Sep 13 - Sep 14
Real Estate: Therapy - Lake, Laundry, Love it
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

3. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is CA $166
CA $297 total
includes taxes & fees
Sep 8 - Sep 9
Private bed with En-suite bathroom Marigold Room
A wooden deck with a table and chairs, surrounded by a white railing.

4. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is CA $433
CA $761 total
includes taxes & fees
Sep 5 - Sep 6
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

5. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (7 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is CA $148
CA $267 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Home in Pownal VT
A hallway with wooden flooring, white walls, and a bed in the background.

6. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is CA $222
CA $504 total
includes taxes & fees
Sep 9 - Sep 10
Cozy private 2 bed apartment in Shelburne Falls
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

7. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is CA $202
CA $521 total
includes taxes & fees
Sep 9 - Sep 10
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A hot tub with a string of lights above it, set against a dark night sky.

8. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $222
CA $546 total
includes taxes & fees
Sep 7 - Sep 8
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

9. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is CA $105
CA $296 total
includes taxes & fees
Sep 10 - Sep 11
NEW RENO - Chalet-style farm loft near Tanglewood
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

10. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is CA $424
CA $678 total
includes taxes & fees
Oct 5 - Oct 6
The Greylock Cabin
A kitchen with white cabinets, a wooden dining table, and pendant lights.

11. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (58 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is CA $316
CA $664 total
includes taxes & fees
Sep 17 - Sep 18
A roomy remodeled retreat close to MassMoCA
A spacious living room with a dining area, a kitchen, and a large window.

12. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is CA $118
CA $310 total
includes taxes & fees
Sep 14 - Sep 15
1800s Carriage house in Berkshires / Hudson Valley

13. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is CA $223
CA $756 total
includes taxes & fees
Sep 7 - Sep 8
Comfortable Berkshires retreat on mtn resort, SISO
A rustic wooden cabin with a chimney, surrounded by a forest.

14. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is CA $265
CA $474 total
includes taxes & fees
Sep 14 - Sep 15
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

15. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveller
The price is CA $350
CA $590 total
includes taxes & fees
Sep 9 - Sep 10
Charming, updated 3 bedroom farmhouse farm stay.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

16. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is CA $243
CA $784 total
includes taxes & fees
Sep 17 - Sep 18
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

17. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is CA $400
CA $827 total
includes taxes & fees
Sep 28 - Sep 29
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A two-story house with a front porch, a small staircase leading to the door, and a pathway flanked by bushes and a lamp post.

18. North Getaway Cottage

North Getaway Cottage
Williamstown
8.8 out of 10, Excellent, (27 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is CA $279
CA $615 total
includes taxes & fees
Sep 17 - Sep 18
North Getaway Cottage
A white two-story house with a porch, surrounded by trees and a hill.

19. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is CA $343
CA $736 total
includes taxes & fees
Sep 14 - Sep 15
1789 Shaker Farmhouse in Berkshires/Hudson Valley
An aerial view of a house surrounded by a forest with autumn foliage.

20. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is CA $312
CA $737 total
includes taxes & fees
Sep 8 - Sep 9
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
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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Top Windsor Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"Clean room nice Kitchenette with everything."
Katherine 2-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
11,060
Accommodation
286 Vacation Homes
Lowest Price
CA $85
Highest Price
CA $338

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