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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Windsor Vacation Homes

Our top choices for Windsor vacation homes

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
The price is CA $316
CA $719 total
includes taxes & fees
Sep 7 - Sep 8
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (255)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is CA $208
CA $310 total
includes taxes & fees
Sep 16 - Sep 17
Berkshire Village Carriage House - Super Private!!
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Dining

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

10.0 out of 10, Exceptional, (3)
"Friends and I were in the area for a concert at Tree House Brewing. This house wasn’t far and it is a gorgeous home. Super clean and had all amenities. Would stay here again!"
The price is CA $236
CA $516 total
includes taxes & fees
Aug 24 - Aug 25
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is CA $225
CA $553 total
includes taxes & fees
Sep 3 - Sep 4
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Fridge, microwave, oven, stovetop

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

10.0 out of 10, Exceptional, (12)
"Great property, plenty of space and room for all. Location is ideal"
The price is CA $323
CA $757 total
includes taxes & fees
Sep 15 - Sep 16
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is CA $534
CA $935 total
includes taxes & fees
Sep 10 - Sep 11
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Smart TV, books

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.8 out of 10, Exceptional, (7)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is CA $222
CA $546 total
includes taxes & fees
Sep 3 - Sep 4
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit
Dining

FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit

9.8 out of 10, Exceptional, (36)
"Great place and convenient to get to and from Berkshire East."
The price is CA $402
CA $895 total
includes taxes & fees
Aug 25 - Aug 26
FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (1)
"Renting this house was very last minute because the place we initially booked fell through - and we're so glad it did! The house was charming, cozy, up-to-date, and beautifully decorated. The neighborhood was nice and quiet, and the drive to downtown was short. I highly recommend this house!"
The price is CA $520
CA $717 total
includes taxes & fees
Aug 24 - Aug 25
Bungalow in the Berkshires
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is CA $415
CA $742 total
includes taxes & fees
Sep 11 - Sep 12
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
North Getaway Cottage
Exterior

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is CA $281
CA $619 total
includes taxes & fees
Aug 25 - Aug 26
North Getaway Cottage
NEW RENO Historic Creamery in Berkshires w/hot tub
Terrace/patio

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (3)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is CA $293
CA $666 total
includes taxes & fees
Sep 17 - Sep 18
NEW RENO Historic Creamery in Berkshires w/hot tub
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

3-bedroom house in beautiful Berkshires, close to amenities!

The price is CA $265
CA $445 total
includes taxes & fees
Aug 26 - Aug 27
3-bedroom house in beautiful Berkshires, close to amenities!
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is CA $223
CA $670 total
includes taxes & fees
Sep 9 - Sep 10
Comfortable Berkshires retreat on mtn resort, SISO
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is CA $760
CA $1,451 total
includes taxes & fees
Aug 25 - Aug 26
Hancock Village Inn at Jiminy Peak
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is CA $340
CA $710 total
includes taxes & fees
Aug 24 - Aug 25
Near Tanglewood: Historic Summer Retreat
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is CA $590
CA $1,106 total
includes taxes & fees
Aug 28 - Aug 29
Spacious 5-bedroom house in charming Lee with WiFi
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets

Elegant Carriage House room with a queen bed and private patio.

The price is CA $310
CA $444 total
includes taxes & fees
Sep 10 - Sep 11
Elegant Carriage House room with a queen bed and private patio.
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Terrace/patio

Historic Berkshires Home Near Tanglewood, Trails & Wineries

9.0 out of 10, Wonderful, (17)
"Of all the properties I have stayed at, this home is my favorite! Excited to be able to stay in a such a historical home in a rich historical area! Amanda was a wonderful host! Provided a comfortable stay. The home had all the necessities! The town has delicious places to eat. Grocery store is great! My hope is to return and spend more time here."
The price is CA $345
CA $717 total
includes taxes & fees
Sep 7 - Sep 8
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is CA $288
CA $417 total
includes taxes & fees
Sep 7 - Sep 8
Experience Timeless Elegance in The Edith Wharton Room!
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"I wish I had known about this place when my kids were young. Perfect family, or adult only spot to unwind and relax in the mountains."
JoAnn 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG