Photo by William E Berry Jr.
Windsor Vacation Rentals
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Vacation Rentals in Windsor
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (174)
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
9.0 out of 10, Wonderful, (32)
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
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Treehouse at Wise Pines- SoBo
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (9)
The price is ¥23,184
per night
May 20 - May 21
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
9.8 out of 10, Exceptional, (157)
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (140)
The price is ¥26,275
per night
May 22 - May 23
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
9.6 out of 10, Exceptional, (69)
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
8.6 out of 10, Excellent, (7)
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
9.8 out of 10, Exceptional, (15)
The price is ¥14,374
per night
May 20 - May 21
Idyllic Lakefront House Suited Two Families
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (141)
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (27)
Killington Center Inn & Suites by Killington VR - Studios
Killington Center Inn & Suites by Killington VR - Studios
10.0 out of 10, Exceptional, (1)
Beautifully renovated with fireplace and coffee bar
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (57)
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
10.0 out of 10, Exceptional, (116)
Lakefront home with amazing views, fireplace, firepit, & gas grill
Lakefront home with amazing views, fireplace, firepit, & gas grill
9.8 out of 10, Exceptional, (58)
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (187)
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
8.0 out of 10, Very Good, (14)
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
9.4 out of 10, Exceptional, (27)
Lake Sunapee Gathering Place, Serene Restored Barn
Lake Sunapee Gathering Place, Serene Restored Barn
10.0 out of 10, Exceptional, (6)
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
10.0 out of 10, Exceptional, (113)
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.
Other types of properties in Windsor you may be interested in
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
7.4 out of 10, Good, (1000)
The price is ¥21,419
per night
Jun 10 - Jun 11
Hotel Coolidge
Hotel Coolidge
8.2 out of 10, Very Good, (1001)
The price is ¥18,044
per night
May 19 - May 20
Hampton Inn White River Junction
Hampton Inn White River Junction
8.6 out of 10, Excellent, (1000)
The price is ¥23,101
per night
May 28 - May 29
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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Frequently asked questions
Recent reviews of Windsor propertiesExpedia verified reviews
5/5 Excellent
"Everything was great"
A verified traveler from Belton stayed at The Shire Woodstock
Posted 3 days ago