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

Windsor Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (15 reviews)
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
United States
Brenda
$168 nightly
The price is $183
Nov 22 - Nov 23
Total with taxes and fees
Fat Sheep Farm & Cabins
A cozy living room with a leather couch, a fireplace, and a television.

2. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
10.0 out of 10, Exceptional, (1 review)
"The Cabin in the Woods looks very rustic on the outside, but a cabin ine the woods should. Inside was a pleasant surprise. Full kitchen, large leather wrap around sofa to watch the LARGE flat-screen TV, large dining room table, 4 bedrooms, and 2 full baths made this a perfect get away place."
United States
Alvin
$445 nightly
The price is $503
Nov 10 - Nov 11
Total with taxes and fees
Cabin on the hill Ascutney Vt - 4 bedrooms
A sunroom with wicker furniture, large windows, and string lights.

3. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (21 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
$212 nightly
The price is $240
Nov 15 - Nov 16
Total with taxes and fees
Addie's Place: A Quiet and Quirky Guesthouse
A wooden cabin interior with a staircase, a sofa, and a table.

4. Adventure Cabin Hot Tub Sauna Trails Game Area

Adventure Cabin Hot Tub Sauna Trails Game Area
Cavendish
10.0 out of 10, Exceptional, (29 reviews)
"A very clean and modern cabin. Loved the amenities like the paddle boards, kayaks and hot tub.!"
United States
Katherine B.
$367 nightly
The price is $395
Nov 11 - Nov 12
Total with taxes and fees
Adventure Cabin Hot Tub Sauna Trails Game Area
A large house with a fire pit and outdoor seating.

5. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
$179 nightly
The price is $200
Nov 8 - Nov 9
Total with taxes and fees
Bridgewater Living - Ben&Jerry Suite
A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

6. Cozy Village Condo-Okemo Shuttle

Cozy Village Condo-Okemo Shuttle
Ludlow
9.8 out of 10, Exceptional, (89 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
$221 nightly
The price is $250
Nov 8 - Nov 9
Total with taxes and fees
Cozy Village Condo-Okemo Shuttle
A cabin interior with a wooden staircase, a kitchen with modern appliances, and large windows offering a forest view.

7. Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails

Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails
Cavendish
10.0 out of 10, Exceptional, (58 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
$367 nightly
The price is $395
Nov 10 - Nov 11
Total with taxes and fees
Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails
A cabin interior with a wooden staircase, kitchen area, and large windows offering a forest view.

8. Lux Cabin Hot-Tub, Sauna, Private Fire Pit, Grill, Snow Shoes

Lux Cabin Hot-Tub, Sauna, Private Fire Pit, Grill, Snow Shoes
Cavendish
10.0 out of 10, Exceptional, (20 reviews)
"Great space with everything you could need. Very clean."
United States
Kristen A.
$367 nightly
The price is $395
Nov 10 - Nov 11
Total with taxes and fees
Lux Cabin Hot-Tub, Sauna, Private Fire Pit, Grill, Snow Shoes
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

9. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
$202 nightly
The price is $228
Nov 11 - Nov 12
Total with taxes and fees
Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
A view of a grassy area with a ski lift and a building in the background.

10. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
$233 nightly
The price is $263
Nov 10 - Nov 11
Total with taxes and fees
Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
A wooden deck with a covered seating area, a grill, and string lights.

11. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (16 reviews)
"Our stay in this tiny home was perfect! Very cozy and private. The host was very responsive and everything was exactly as described."
United States
Kat V.
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
A golf course with a winding path, trees, and a hilly landscape.

12. First-floor downtown studio near dining and gear shops, under a mile to Okemo

First-floor downtown studio near dining and gear shops, under a mile to Okemo
Ludlow
8.8 out of 10, Excellent, (14 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
$270 nightly
The price is $305
Nov 10 - Nov 11
Total with taxes and fees
First-floor downtown studio near dining and gear shops, under a mile to Okemo
A large house with a fire pit and outdoor seating.

13. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
$178 nightly
The price is $199
Nov 8 - Nov 9
Total with taxes and fees
Bridgewater Living - Ski VT Suite
A two-story house with a porch, a staircase, and a front door.

14. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

Downtown Ludlow condo with electric fireplace, shuttle stop across the street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"Easy stay. Great location."
United States
Zach S.
$242 nightly
The price is $273
Nov 10 - Nov 11
Total with taxes and fees
Downtown Ludlow condo with electric fireplace, shuttle stop across the street
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

15. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Had a lot here to use and The place was very cute. It’s good if you have small kids they have a lot for that sort of thing. Very clean as well"
United States
sean c.
$363 nightly
The price is $393
Nov 10 - Nov 11
Total with taxes and fees
Lakefront Family Fun Retreat
A modern cabin with a deck, surrounded by a forest.

16. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
Hartford
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful and well appointed abode - super cozy!"
United States
Nina S.
$765 nightly
The price is $864
Nov 10 - Nov 11
Total with taxes and fees
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
A golf course with a winding path, trees, and a distant mountain range.

17. Compact downtown studio condo with kitchenette near the Okemo slopes

Compact downtown studio condo with kitchenette near the Okemo slopes
Ludlow
8.6 out of 10, Excellent, (34 reviews)
"the home was clean and very nice. "
United States
Frank R.
$208 nightly
The price is $235
Nov 10 - Nov 11
Total with taxes and fees
Compact downtown studio condo with kitchenette near the Okemo slopes
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

18. Mountain Green ground-floor condo with private yard off the patio

Mountain Green ground-floor condo with private yard off the patio
Killington
$253 nightly
The price is $286
Nov 10 - Nov 11
Total with taxes and fees
Mountain Green ground-floor condo with private yard off the patio
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

19. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Great room!"
United States
Carla M.
$228 nightly
The price is $258
Nov 8 - Nov 9
Total with taxes and fees
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
A large house with a fire pit and outdoor seating.

20. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Pet Friendly | Game Room | Minutes to Woodstock and Killington
Bridgewater
10.0 out of 10, Exceptional, (4 reviews)
"We loved the farmhouse. It was very charming and cozy. Plenty of space for us and exactly as advertised. We would definitely stay here again. Thank you"
United States
Lisa G.
$446 nightly
The price is $499
Nov 11 - Nov 12
Total with taxes and fees
Pet Friendly | Game Room | Minutes to Woodstock and Killington
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

Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

8/10 Good
"The complimentary breakfast buffet was excellent and provides great value. I’d like to call out “Roberta” who works in the breakfast area. She is very friendly and goes well above and beyond her required duties to make guests comfortable and satisfied. The fitness center is a great amenity. The room was clean. However, our room was not cleaned per the communicated schedule (Sat, Mon, Wed). It was cleaned after our first day (Sat). However they missed Monday. I requested it to be cleaned on Tuesday and they did so. However, it was not cleaned again by the time we checked out on Friday. The air conditioning was also out for our entire stay. Fortunately it was temperate and not needed. But overall the hotel provides good value and quality for the money. We’re likely to stay again unless prices change significantly. One nice thing would be to have recycle containers in the room. The other hotels we stay at in the area usually do. And with the limited cleaning it would be nice to have more or bigger garbage cans."
James 5-night trip
Posted 12 hours ago
Holiday Inn Express Hotel & Suites White River Junction by IHG

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $183 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: You might want to consider this vacation home rental near Windsor, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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.