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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Windsor vacation 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 NT$4,241
NT$6,363 total
includes taxes & fees
Nov 3 - Nov 4
Fat Sheep Farm & Cabins
A picnic table and a fire pit by a lake with a forest in the background.

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 NT$4,757
NT$9,529 total
includes taxes & fees
Oct 15 - Oct 16
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

3. 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 NT$5,874
NT$9,561 total
includes taxes & fees
Oct 20 - Oct 21
Brook Road Condo
Aerial view

4. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is NT$7,255
NT$15,004 total
includes taxes & fees
Oct 13 - Oct 14
The Suites at Killington Center
An aerial view of a residential area with houses, a swimming pool, and a mountain backdrop.

5. Killington Center 531

Killington Center 531
3.5 star property
Killington
Killington Center 531
A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

6. 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 NT$5,862
NT$9,547 total
includes taxes & fees
Oct 29 - Oct 30
Brook Road Cabin
A spacious living area with a fireplace, a dining area, and a kitchen.

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

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is NT$43,866
NT$68,659 total
includes taxes & fees
Oct 11 - Oct 12
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Room

8. Cozy Hotel Room Style Studio Condo With Pool

Cozy Hotel Room Style Studio Condo With Pool
3.0 star property
Killington
Cozy Hotel Room Style Studio Condo With Pool
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

8/10 Good
"Y"
Arthur 3-night trip
Posted 11 hours ago
Align Inn Vermont

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.

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.