Windsor Vacation Rentals
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Vacation Rentals in Windsor
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
The price is $532 per night
$532
includes taxes & fees
$489 per night
Nov 24 - Nov 25
With a stay at this vacation home, you'll be centrally located in Hancock, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Pool
Hot Tub
Amore Estate - beautiful room with many places to explore and relax in.
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Wyndhurst Golf & Club and Berkshire Scenic Railway Museum.
Pool
Hot Tub
Secluded Family Home in Serene Stockbridge Woods
Located in South Lee, this vacation home is in a rural location, within a 5-minute drive of Berkshire Botanical Garden and Housatonic River.
Kitchen
Washer
Berkshire Village Carriage House - Super Private!!
The price is $221 per night
$221
includes taxes & fees
$198 per night
Nov 25 - Nov 26
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Kitchen
Free WiFi
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Located in Whitingham, this vacation home is on the waterfront, within a 15-minute walk of Harriman Reservoir and Green Mountain National Forest.
Hot Tub
Kitchen
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Berkshire Botanical Garden and Tanglewood Music Center.
Hot Tub
Kitchen
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
A stay at this vacation home places you in the heart of Adams, steps from Mount Greylock State Reservation and 7 minutes by foot from East Hoosac Quaker Meetinghouse.
Kitchen
Washer
Tranquil 3-BR Waterfront Retreat
Located in Becket, this vacation home is on the waterfront, within a 5-minute drive of Pyramid Lake and Jacob's Pillow.
Kitchen
Washer
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Located in Lenox, this vacation home is within a 15-minute walk of Pleasant Valley Wilderness Sanctuary and Kennedy Park.
Kitchen
Washer
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Located in Shelburne Falls, this vacation home is in a rural location, within a 5-minute drive of Deerfield River and Bald Mountain Pottery.
Pool
Kitchen
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.
Windsor Vacation Rentals essential information
Accommodation | 213 Vacation Rentals |
|---|---|
Lowest Price | $221 |
Highest Price | $532 |
Popular accommodation | Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con, Amore Estate - beautiful room with many places to explore and relax in., Secluded Family Home in Serene Stockbridge Woods, Berkshire Village Carriage House - Super Private!!, Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating , Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Cozy Home In The Berkshires, Pet Friendly with fenced in yard!, Tranquil 3-BR Waterfront Retreat, Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, 1810 Brook Side Mill/House / EV Level 2 Charging on Site, Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond, Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Friendly! Mountain Views! |