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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
$177 nightly
The price is $193
Nov 5 - Nov 6
Total with taxes and fees
Fat Sheep Farm & Cabins
A person standing on a sandy beach by a river with trees in the background.

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
$483 nightly
The price is $546
Oct 20 - Oct 21
Total with taxes and fees
Cabin on the hill Ascutney Vt - 4 bedrooms
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

3. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (29 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
$378 nightly
The price is $407
Nov 11 - Nov 12
Total with taxes and fees
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
A sunroom with wicker furniture, large windows, and string lights.

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

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (19 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
$206 nightly
The price is $233
Oct 27 - Oct 28
Total with taxes and fees
Addie's Place: A Quiet and Quirky Guesthouse
A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

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.
$184 nightly
The price is $206
Nov 3 - Nov 4
Total with taxes and fees
Bridgewater Living - Ben&Jerry Suite
A cozy living room with a sectional sofa, a fireplace, a flat-screen TV, and a bookshelf.

6. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
Hartford
10.0 out of 10, Exceptional, (179 reviews)
"Clean, well maintained property. Perfect decor for a quaint Vermont town."
United States
Joann
$379 nightly
The price is $428
Oct 25 - Oct 26
Total with taxes and fees
Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

7. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (55 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
$377 nightly
The price is $406
Nov 9 - Nov 10
Total with taxes and fees
Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

8. Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards

Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards
Cavendish
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful property, quiet and peaceful location. Enjoyed the access to the hot tub, and loved having a private fire pit."
United States
David V.
$377 nightly
The price is $406
Nov 9 - Nov 10
Total with taxes and fees
Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards
A picnic table and a fire pit by a lake with a forest in the background.

9. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
$308 nightly
The price is $339
Oct 19 - Oct 20
Total with taxes and fees
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

10. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
$205 nightly
The price is $232
Oct 19 - Oct 20
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

11. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
$261 nightly
The price is $295
Oct 25 - Oct 26
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
A view of a grassy area with a ski lift and a building in the background.

12. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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.
$236 nightly
The price is $266
Oct 19 - Oct 20
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

13. Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
$256 nightly
The price is $290
Oct 19 - Oct 20
Total with taxes and fees
Welcoming condo near the slopes with free WiFi and full kitchen
A room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

14. 180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
Hartford
9.0 out of 10, Wonderful, (8 reviews)
"Plenty of room beautiful view"
United States
Anthony A.
$484 nightly
The price is $547
Oct 26 - Oct 27
Total with taxes and fees
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
A two-story house with a porch, a staircase, and a front door.

15. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"You better ask for one of the rear units because the front one is practically in the middle of the road. It’s noisy. It’s dingy, the owner refused to let us check in an hour early, which actually worked out in our favor since we didn’t want to stay there after we saw the place. We asked to move to a rear unit. The answer was no. We didn’t ask for a refund. We just went and booked another room and left this place empty for the night. There are so many other nice places to stay in this area. I...
United States
William
$240 nightly
The price is $271
Oct 19 - Oct 20
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
A golf course with a winding path, trees, and a hilly landscape.

16. Well-appointed studio right downtown - less than a mile to Okemo Mountain

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.8 out of 10, Excellent, (13 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
$273 nightly
The price is $309
Oct 21 - Oct 22
Total with taxes and fees
Well-appointed studio right downtown - less than a mile to Okemo Mountain
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

17. 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.
$381 nightly
The price is $413
Nov 3 - Nov 4
Total with taxes and fees
Lakefront Family Fun Retreat
A large indoor swimming pool with clear lanes, wooden beams, and seating areas.

18. 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.
$789 nightly
The price is $892
Oct 19 - Oct 20
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.

19. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (34 reviews)
"the home was clean and very nice. "
United States
Frank R.
$202 nightly
The price is $229
Oct 19 - Oct 20
Total with taxes and fees
Efficient condo near slopes with kitchenette & great location
A spacious living room with a stone fireplace, wooden furniture, and large windows.

20. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
$618 nightly
The price is $692
Oct 31 - Nov 1
Total with taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
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

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

8/10 Good
"Pool was cold."
Dexter 1-night trip
Posted 6 hours ago
Hideaway Inn Mt.Sunapee

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 $193 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.