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Vacation Rentals in Windsor

Estimated price for 1 night/2 adults

Jackson Gore Village
Jackson Gore Village
3.0 out of 5.0 111 Jackson Gore Road, Ludlow, VT
CA $184
4.2/5 (376 reviews)

Staff were super friendly. Modern facility with great views.

Reviewed on Oct. 18, 2019
Offering ski-in/ski-out access, this condo in Ludlow is located in the mountains, within 1 mile (2 km) of Okemo Valley Golf Club and Jackson Gore Ski Resort ...
Winterplace at Okemo
Winterplace at Okemo
4.0 out of 5.0 77 Okemo Ridge Rd, Ludlow, VT
CA $237
3.5/5 (6 reviews)

There was only 1 bar of soap and bottle of shampoo for my 4 night stay

Reviewed on Oct. 17, 2019
Situated in Ludlow, this condominium resort is within 1 mi (2 km) of Dorsey Park and Okemo Mountain Resort. Jackson Gore Ski Resort at Okemo is 2.6 mi (4.1 km) ...
Highridge Condominiums
Highridge Condominiums
3.5 out of 5.0 184 High Ridge Road, Killington, VT
CA $337
4.5/5 (20 reviews)

great... Just what we expected. Off in the woods but easy to find

Reviewed on Oct. 7, 2019
Located in Killington Ski Area, this golf condo is 1.3 mi (2 km) from Killington Golf Course and 2.2 mi (3.6 km) from Killington Resort. Pico Mountain at Killington ...
Fall Line Condominiums
Fall Line Condominiums
3.5 out of 5.0 786 E Mountain Road, Killington, VT
CA $230
4.0/5 (13 reviews)

First, want to say I LOVE this place. Never given it anything less than 5 star rating, been staying here at least once a year for almost 10 years. One of the best for boarding/skiing Killington. But this stay was horrible (first and only time out of many - want to clarify EVERY other visit was 5 ...

Reviewed on Feb. 18, 2019
Located in Killington Ski Area, this condo is 0.5 mi (0.8 km) from Killington Golf Course and 1.4 mi (2.3 km) from Killington Resort. Gifford Woods State Park ...
Mountain Green Condo
Mountain Green Condo
3.0 out of 5.0 133 E Mountain Road, Killington, VT
4.3/5 (12 reviews)

Excellent option for the Spartan race with a large group.

Reviewed on Nov. 6, 2019
Located in Killington Ski Area, this golf condominium resort is within 1 mile (2 km) of Killington Golf Course and Killington Resort. Pico Mountain at Killington ...
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 out of 5.0 3387 East Mountain Road, Killington, VT
4.7/5 (3 reviews)

Outstanding stay at the Spruce Glen resort! The townhome was so spacious, had everything you needed, quiet, beautiful setting! Quick drive to outstanding disc golf and tasty restaurants. Ready to re-book. Don't hestitate on this place Ryan is available if you need anything! Good times by all even ...

Reviewed on Oct. 1, 2019
Located in Killington Ski Area, this apartment building is 3 mi (4.9 km) from Killington Golf Course and within 9 miles (15 km) of Killington Resort and Pico ...
Solitude Village at Okemo
Solitude Village at Okemo
4.0 out of 5.0 77 Okemo Ridge Rd, Ludlow, VT
CA $217
3.8/5 (5 reviews)

Beautiful setting, room was nice but poorly supplied with utensils to cook in.

Reviewed on Nov. 2, 2019
Situated in Ludlow, this condominium resort is within 1 mi (2 km) of Dorsey Park and Okemo Mountain Resort. Jackson Gore Ski Resort at Okemo is 2.6 mi (4.1 km) ...
Top-floor Condo w/ Shared Pool, hot Tub, Sauna & View of the Slopes
Top-floor Condo w/ Shared Pool, hot Tub, Sauna & View of the Slopes
133 East Mountain Road, Unit 3F08, Killington, VT
CA $65
4.3/5 (3 reviews)

In walking distance to bike park and hiking trails. Try the Garlic Restaurant!

Reviewed on Aug. 31, 2019
Located in Killington Ski Area, this romantic condo is within 1 mile (2 km) of Killington Golf Course and Killington Resort. Pico Mountain at Killington Ski ...
'deluxe' Slopeside MT Green 1 Bedrm Condo
'deluxe' Slopeside MT Green 1 Bedrm Condo
133 E. Mountain Rd, Killington, VT
4.0/5 (3 reviews)

Clean small one bedroom that is a 3 min drive to the K-1 lift. As advertised by owner. We would rent again.

Reviewed on Feb. 24, 2019
Located in Killington Ski Area, this condo is within 1 mi (2 km) of Killington Golf Course and Killington Resort. Pico Mountain at Killington Ski Resort and ...
Map

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Other types of properties in Windsor you may be interested in

Estimated price for 1 night/2 adults

Windsor Mansion Inn

Windsor Mansion Inn

153 Pembroke Road, Windsor, VT
    3.5 out of 5.0
     
     

    Windsor Mansion InnCA $114

    Nov. 13 - Nov. 14

    Windsor Mansion InnCA $114
    Snapdragon Inn

    Snapdragon Inn

    26 Main Street, Windsor, VT
      3.5 out of 5.0
       
       

      Snapdragon InnCA $231

      Nov. 14 - Nov. 15

      Snapdragon InnCA $231