A snow-covered river valley with a bridge and a town.

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Windsor holiday rentals

Exterior

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is Rp4.268.434
Rp5.627.980 total
includes taxes & fees
1 Sept - 2 Sept
Fat Sheep Farm & Cabins
House (2 Bedrooms) | Interior

2. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is Rp5.082.748
Rp7.999.243 total
includes taxes & fees
12 Aug - 13 Aug
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Aerial view

3. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is Rp1.396.861
Rp4.165.444 total
includes taxes & fees
11 Aug - 12 Aug
Mountain Green
Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix

4. Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.4 out of 10, Good, (10 reviews)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
The price is Rp3.075.746
Rp5.126.258 total
includes taxes & fees
10 Aug - 11 Aug
Brook Road Cabin
Condo, 2 Bedrooms | Living area

5. The Woods by Killington Vacation Rentals - 2 Bedrooms

The Woods by Killington Vacation Rentals - 2 Bedrooms
3.0 star property
The Woods
10.0 out of 10, Exceptional, (3 reviews)
"The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again."
United States
Paul
The price is Rp4.161.721
Rp11.748.703 total
includes taxes & fees
31 Aug - 1 Sept
The Woods by Killington Vacation Rentals - 2 Bedrooms
House (5 Bedrooms) | Front of property

6. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is Rp21.297.430
Rp34.264.343 total
includes taxes & fees
12 Aug - 13 Aug
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Condo, 1 Bedroom | Interior

7. Killington Center Inn & Suites by Killington VR - 1 Bedrooms

Killington Center Inn & Suites by Killington VR - 1 Bedrooms
3.0 star property
Killington
2.0 out of 10, (1 review)
"This place does not have clean water. The water that comes from the faucets is brown and there are notices on the doors about high levels of carcinogens. "
United States
Tyler
The price is Rp3.771.435
Rp10.129.186 total
includes taxes & fees
8 Sept - 9 Sept
Killington Center Inn & Suites by Killington VR - 1 Bedrooms
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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Top Windsor Hotel Reviews

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Great location. Great staff including the owner. Very nicely maintained. Convenient location. Great breakfast and afternoon cookies was a plus."
Donna and Dixie Barnhart 1-night trip
Posted 4 hours ago
Align Inn Vermont

Find out more about Windsor

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

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

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to Maze of Adventure, 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 scenic spots to enjoy the outdoors, whereas American Precision Museum is one of the cultural attractions. Other places in town to visit include Mt Ascutney State Park and Old Constitution House.

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.