Photo by William E Berry Jr.

Windsor Vacation Rentals

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Vacation Rentals in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, 32 reviews
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Killington Center Inn & Suites by Killington VR - Studios
Studio | Aerial view
Killington Center Inn & Suites by Killington VR - Studios
3.0 star property
10.0 out of 10, Exceptional, 1 review
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
Killington Center Inn & Suites by Killington VR - Studios
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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

White River Inn and Suites
Indoor pool
White River Inn and Suites
2.5 star property
7.2 out of 10, Good, 1,001 reviews
"I was there for the CBHM Race and this place was convenient in terms of location. Outside was well kept. Inside was a little run-down but it was clean. "
The price is NT$5,739
per night
Jun 24 - Jun 25
White River Inn and Suites
Killington Mountain Lodge, Tapestry Collection by Hilton
Terrace/patio
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
7.4 out of 10, Good, 1,001 reviews
"Nice buffet "
The price is NT$4,482
per night
Jun 26 - Jun 27
Killington Mountain Lodge, Tapestry Collection by Hilton
Hotel Coolidge
Front of property - evening/night
Hotel Coolidge
3.0 star property
8.2 out of 10, Very Good, 1,007 reviews
"I love visiting Hotel Coolidge. It's quaint, it's quiet, the small town has grown a lot and for me, it was convenient, affordable for a small in and the charm that makes me happy. And Andrew on the front desk is the best. I will be back!!"
The price is NT$4,569
per night
Jun 26 - Jun 27
Hotel Coolidge
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.

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we offer vacation rentals in Windsor close to The Sustainable Farmer, or you can select a more secluded option if you're looking for extra privacy while you relax. Windsor is known for its breweries and golf courses. Make sure you have time to check out the forests while you're in the area.

How many vacation rentals are there in Windsor?

With 12 Expedia vacation rentals, you're sure to find just the right place for your Windsor stay.

What can I see and do in Windsor?

Mt Ascutney State Park and Connecticut River are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include The Sustainable Farmer. Other places in town to visit include American Precision Museum and Harpoon Brewery.

What are vacation rentals like in Windsor?

Vacation rentals are private properties you can stay in for several days or more in Windsor. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family gatherings.

Recent reviews of Windsor properties
Expedia verified reviews

Woodstock Inn & Resort

Woodstock Inn & Resort

5/5 Excellent
"Absolutely flawless!!!"
A verified traveler stayed at Woodstock Inn & Resort
Posted 2 days ago
Woodstock Inn & Resort