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

Our top choices for Windsor vacation 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 ￥33,186
￥44,771 total
includes taxes & fees
Sep 1 - Sep 2
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 ￥44,804
￥70,513 total
includes taxes & fees
Aug 15 - Aug 16
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix

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 ￥27,328
￥45,547 total
includes taxes & fees
Aug 12 - Aug 13
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 ￥12,313
￥36,717 total
includes taxes & fees
Aug 27 - Aug 28
Mountain Green
House, 6 Bedrooms | Living area

5. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is ￥35,869
￥118,066 total
includes taxes & fees
Aug 12 - Aug 13
Breakaway House by Killington Vacation Rentals
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 ￥187,734
￥302,036 total
includes taxes & fees
Aug 15 - Aug 16
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Condo, 2 Bedrooms | 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 price is ￥36,978
￥104,391 total
includes taxes & fees
Aug 31 - Sep 1
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 13 hours ago
Hilton Garden Inn Hanover Lebanon

Find out more about Windsor

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:

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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 vacation rental in Windsor?

Yes, we offer vacation rentals in Windsor close to Maze of Adventure, 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.

What's the top vacation rental that Windsor has to offer?

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock: You might want to consider this vacation home rental near Windsor, which is located on a river and has an outdoor pool, a fireplace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Windsor?

With 11 Expedia vacation rentals, you're sure 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 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.