Windsor Vacation Rentals
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Browse Select Windsor Vacation Homes
Our top choices for Windsor vacation homes

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!
10.0 out of 10, Exceptional, (1)
The price is CA $316
CA $719 total
includes taxes & fees
Sep 7 - Sep 8

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (255)
The price is CA $208
CA $310 total
includes taxes & fees
Sep 16 - Sep 17

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
10.0 out of 10, Exceptional, (3)
The price is CA $236
CA $516 total
includes taxes & fees
Aug 24 - Aug 25

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
10.0 out of 10, Exceptional, (3)
The price is CA $225
CA $553 total
includes taxes & fees
Sep 3 - Sep 4

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
10.0 out of 10, Exceptional, (12)
The price is CA $323
CA $757 total
includes taxes & fees
Sep 15 - Sep 16

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
10.0 out of 10, Exceptional, (2)
The price is CA $534
CA $935 total
includes taxes & fees
Sep 10 - Sep 11

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.8 out of 10, Exceptional, (7)
The price is CA $222
CA $546 total
includes taxes & fees
Sep 3 - Sep 4

FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit
FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit
9.8 out of 10, Exceptional, (36)
The price is CA $402
CA $895 total
includes taxes & fees
Aug 25 - Aug 26
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.
Save an average of 15% on thousands of hotels when you're signed in
Top Windsor Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
10/10 Excellent
Find out more about Windsor
Find out more about Windsor
Windsor Vacation Homes information
Number of reviews | 770 |
---|---|
Accommodation | 299 Vacation Homes |
Lowest Price | CA $223 |
Highest Price | CA $590 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
Top Vacation Homes in Other Destinations
More Accommodation Types in Windsor
- Apartments in Windsor
- Cottages in Windsor
- Condo Rentals in Windsor
- Resorts in Windsor
- Cabin Rentals in Windsor
- Farmstay in Windsor
- Motels in Windsor
- B&B in Windsor
- Guest Houses in Windsor
- Aparthotels in Windsor
- Chalets in Windsor
- Inns in Windsor
- Villas in Windsor
- Condo Resorts in Windsor
- Lodges in Windsor
- RV Parks in Windsor
- Castles in Windsor
- Hotels
All Accommodation Types
Be inspired: Top Vacation Homes destinations in 2025
- Orlando Vacation Homes
- Florida Vacation Homes
- Kissimmee Vacation Homes
- Hawaii Vacation Homes
- Costa Rica Vacation Homes
- Walt Disney World® Vacation Homes
- Palm Springs Vacation Homes
- Naples Vacation Homes
- Victoria Vacation Homes
- Kelowna Vacation Homes
- Toronto Vacation Homes
- Las Vegas Vacation Homes
- Vancouver Vacation Homes
- Mexico Vacation Homes
- Phoenix Vacation Homes
- Fort Lauderdale Vacation Homes
- Davenport Vacation Homes
- Myrtle Beach Vacation Homes
- Los Angeles Vacation Homes
- Cape Coral Vacation Homes
More ways to book
Expedia's Latest Trends
Hotels