Photo by William E Berry Jr.

Search Holiday Rentals in Windsor

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Check prices for these dates

Tonight
25 Mar - 26 Mar
Tomorrow
26 Mar - 27 Mar
This weekend
28 Mar - 30 Mar
Next weekend
4 Apr - 6 Apr

Top Holiday Rentals in Windsor

Mountain Green
Indoor pool

Mountain Green

2.0 star property
6.4 out of 10, (9)
"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "
The price is ฿7,371
฿9,888 total
includes taxes & fees
7 Apr - 8 Apr
Mountain Green
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Solitude Village at Okemo
Solitude Village Two Bedroom Suite Mountainside | Private kitchen | Fridge, microwave, stovetop, toaster

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very good, (25)
"Very friendly costumer service, we arrived late and we're greated with kindness. "
Solitude Village at Okemo
Okemo Mountain Lodging
Full-sized fridge, microwave, oven, stovetop

Okemo Mountain Lodging

3.5 star property
7.8 out of 10, Good, (27)
"I had an amazing time with my family, I will definitely be coming back "
Okemo Mountain Lodging
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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Other types of properties in Windsor you may be interested in

Fat Sheep Farm & Cabins
Exterior

Fat Sheep Farm & Cabins

3.0 star property
9.6 out of 10, Exceptional, (9)
"Honestly as soon as I got there I knew I had made a good choice. Then I stepped into the cabin and knew I had made an excellent choice. It’s by far the cleanest place Ive stayed. I went looking for peace and quiet and I got just that. It’s silent, it’s beautiful, it’s private. Even though it’s deep winter I still got to hang in the barn, feed the animals, go on quiet hikes. The animals are extremely friendly, they’re are used to people and enjoy being petted. There’s this super nice lady who...
The price is ฿5,377
฿7,520 total
includes taxes & fees
6 Apr - 7 Apr
Fat Sheep Farm & Cabins
Align Inn Vermont
Combined shower/bathtub, eco-friendly toiletries, hair dryer, towels

Align Inn Vermont

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Very good😁👍"
The price is ฿3,699
฿4,069 total
includes taxes & fees
8 Apr - 9 Apr
Align Inn Vermont
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (504)
"The Woodstock Inn & Resort is the quintessential New England inn. Walk in the lobby and you are greeted by a large warm fire. The staff at all levels were gracious and helpful. The room was large, well decorated and extremely comfortable. Great location to walk downtown even with single digit temperatures. The shops were expensive but worth browsing & buying. "
The price is ฿10,112
฿12,611 total
includes taxes & fees
20 Apr - 21 Apr
Woodstock Inn & Resort
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.

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to The Sustainable Farmer, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals are there in Windsor?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Windsor stay.

What can I see and do in Windsor?

Connecticut River and Paradise Park 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 holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.