Windsor County Holiday Homes
Choose from over 1,000,000 unique hotels, apartments & villas around the world
Get the best price available with ebookers Price GuaranteeOpens in a new window
Free cancellation on most hotels when you book with ebookers!*
Featured Holiday Homes in Windsor County
Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base
Ludlow VT
During your stay at this holiday home, you'll be within walking distance of Dorsey Park. Laundry facilities are available. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Küche
Waschmaschine
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Ludlow VT
During your stay at this holiday home, you'll be within walking distance of Okemo Mountain Resort. You'll find features such as 1 hot tub and laundry facilities. Enjoy your stay with amenities like a kitchen and 2 bathrooms in the holiday home.
Whirlpool
Küche
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
Plymouth VT
During your stay at this holiday home, you'll be close to Amherst Lake. Features include 1 hot tub and laundry facilities. The holiday home includes amenities such as a kitchen and 2 bathrooms.
Whirlpool
Küche
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Ludlow VT
During your stay at this holiday home, you're just a quick walk from Fletcher Farm School for the Arts and Crafts. Enjoy features like laundry facilities and an arcade/games room. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Küche
Waschmaschine
Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock
Hartford VT
This holiday home's great location gets high marks from our customers. During your stay, you'll be within walking distance of The Strong House Spa. Features include an indoor pool, a gym and concierge services. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Pool
Küche
Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola
Bridgewater Corners VT
During your stay at this holiday home, you'll be close to Killington Resort. You'll find features such as 1 hot tub and laundry facilities. The holiday home includes amenities such as free WiFi and a kitchen.
Whirlpool
Küche
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
Ludlow VT
During your stay at this holiday home, you'll be within walking distance of Lake Rescue. You'll find features such as 1 hot tub and laundry facilities. Enjoy your stay with amenities like free WiFi and in-room jetted baths in the holiday home.
Whirlpool
Küche
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Woodstock VT
During your stay at this holiday home, you'll be close to Union Arena Community Center. Laundry facilities are available. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Küche
Waschmaschine
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Ludlow VT
During your stay at this holiday home, you're just a quick walk from Lake Rescue. You'll find features such as laundry facilities. The holiday home includes amenities such as a kitchen and 2 bathrooms.
Küche
Waschmaschine
Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE
Ludlow VT
During your stay at this holiday home, you'll be within walking distance of Okemo Mountain Resort. Features include 1 hot tub, laundry facilities and an arcade/games room. The holiday home includes amenities such as free WiFi and a kitchen.
Whirlpool
Küche
Walk to Trails & Village +Pets - Highland Cabin
Woodstock VT
During your stay at this holiday home, you're just a quick walk from Billings Park and Trail. The holiday home includes amenities such as a kitchen and a balcony.
Küche
Waschmaschine
New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow VT
During your stay at this holiday home, you'll be within walking distance of Dorsey Park. Enjoy features like laundry facilities. The holiday home offers free WiFi and a kitchen.
Küche
Waschmaschine
Minutes to Skiing/Hot Tub/Arcades
Bridgewater Corners VT
During your stay at this holiday home, you'll be close to Long Trail Brewing Company. 1 hot tub, laundry facilities and an arcade/games room are available. The holiday home includes amenities such as free WiFi and a kitchen.
Whirlpool
Küche
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Plymouth VT
During your stay at this holiday home, you'll be close to Killington Resort. Free WiFi in public areas and laundry facilities are available. The holiday home offers a kitchen and a washer/dryer.
Küche
Waschmaschine
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 County Holiday Homes essential information
Accommodation | 444 Holiday Homes |
|---|---|
Lowest Price | |
Highest Price | |
Popular accommodation | Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Rustic home with a private hot tub, fireplace, cable, & washer/dryer, Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo, Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock, Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola, Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!, PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC., Lakefront house with skiing nearby, dock, and amazing views - dog-friendly, Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE, Walk to Trails & Village +Pets - Highland Cabin, New Ludlow Village Home with Stunning Okemo Mountain View, Minutes to Skiing/Hot Tub/Arcades, Dog-friendly cabin with forest setting, woodstove & deck - near Killington, BRIDGEWATER RETREAT |