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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Windsor holiday rentals

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

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 Rp3.830.859
Rp5.148.298 total
includes taxes & fees
22 Oct - 23 Oct
Fat Sheep Farm & Cabins
A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

2. 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 Rp3.047.431
Rp5.079.067 total
includes taxes & fees
23 Sept - 24 Sept
Brook Road Cabin
An aerial view of a residential area with houses, a swimming pool, and a mountain backdrop.

3. Killington Center 531

Killington Center 531
3.5 star property
Killington
The price is Rp3.143.166
Rp5.508.766 total
includes taxes & fees
24 Sept - 25 Sept
Killington Center 531
A spacious living area with a fireplace, a dining area, and a kitchen.

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

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is Rp24.399.492
Rp38.190.000 total
includes taxes & fees
23 Sept - 24 Sept
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

5. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is Rp3.033.990
Rp7.263.729 total
includes taxes & fees
24 Sept - 25 Sept
The Suites at Killington Center
A snow-covered residential area with multi-story buildings, a ski slope in the background, and a clear sky.

6. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"I enjoy the location "
United States
troy
The price is Rp1.386.012
Rp4.133.094 total
includes taxes & fees
27 Sept - 28 Sept
Mountain Green

7. Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
2.0 star property
Killington
The price is Rp2.450.604
Rp4.746.948 total
includes taxes & fees
24 Sept - 25 Sept
Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

8. Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3 reviews)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is Rp3.267.472
Rp5.317.811 total
includes taxes & fees
19 Oct - 20 Oct
Brook Road Condo
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

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"This is a beautiful clean well accommodated property on the edge of a magnificent pond. Ive nothing but positive memories and will definitely return."
E William 1-night trip
Posted 6 hours ago
Mountain Meadows Lodge

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 Harpoon Brewery and Mt Ascutney State Park.

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.