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

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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 RM878
RM1,180 total
includes taxes & fees
7 Sept - 8 Sept
Fat Sheep Farm & Cabins
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 RM1,162
RM1,828 total
includes taxes & fees
12 Aug - 13 Aug
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Living room

3. 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 RM702
RM1,170 total
includes taxes & fees
12 Aug - 13 Aug
Brook Road Cabin
Aerial view

4. 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 RM319
RM952 total
includes taxes & fees
12 Aug - 13 Aug
Mountain Green
Living area

5. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is RM950
RM3,065 total
includes taxes & fees
12 Aug - 13 Aug
Breakaway House by Killington Vacation Rentals
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 RM4,868
RM7,832 total
includes taxes & fees
12 Aug - 13 Aug
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Living area

7. 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 Woods by Killington Vacation Rentals - 2 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

Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon

10/10 Excellent
"The parking lot was huge and well lit, the landscaping was beautiful and meticulously maintained. The outdoor patio was really pretty and we sat there for breakfast every morning (the inside was nice and clean too!) the wildflowers and plantings were really peaceful to look at. The room was huge (301) and was very quiet and clean, the decor was very modern and updated. The bed was really comfortable so we slept great and the shower was awesome! The design was cool but the water pressure was great. The shampoo & conditioner was sulfate free so I could use it in my colored hair which is unusual for a hotel and the Crabtree & Evelyn Body wash was great- I’m buying it for home. The breakfast buffet was good- had all the basics… fresh fruit, yogurt, eggs, bacon, sausage, oatmeal, pastries, bagels etc and more. The staff was very nice and helpful."
Deborah 2-night trip
Posted 11 hours ago
Hilton Garden Inn Hanover Lebanon

Find out more about Windsor

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

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  • 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 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.