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

Windsor Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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
$286 nightly
The price is $312
Sep 7 - Sep 8
Total with taxes and fees
Fat Sheep Farm & Cabins
Beach

2. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
$467 nightly
The price is $528
Sep 4 - Sep 5
Total with taxes and fees
Cabin on the hill Ascutney Vt - 4 bedrooms
Smart TV, fireplace, DVD player, books

3. Modern Rustic Cabin #2 - Panoramic forest views, private firepit, 24/7 hot-tub!

Modern Rustic Cabin #2 - Panoramic forest views, private firepit, 24/7 hot-tub!
Cavendish
10.0 out of 10, Exceptional, (27 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
$330 nightly
The price is $353
Sep 2 - Sep 3
Total with taxes and fees
Modern Rustic Cabin #2 - Panoramic forest views, private firepit, 24/7 hot-tub!
Exterior detail

4. Cozy Chic! Cabin #3: wooded delights with year-round hot-tub and private firepit

Cozy Chic! Cabin #3: wooded delights with year-round hot-tub and private firepit
Cavendish
10.0 out of 10, Exceptional, (53 reviews)
"We had a fantastic stay! Can’t wait to return for a summer or fall trip. Cabin was wonderful, clean and full of amenities. It is a plus having access to laundry services."
United States
John H.
$359 nightly
The price is $386
Sep 3 - Sep 4
Total with taxes and fees
Cozy Chic! Cabin #3: wooded delights with year-round hot-tub and private firepit
Interior

5. Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
$543 nightly
The price is $608
Sep 2 - Sep 3
Total with taxes and fees
Terrific 3-bedroom cottage with AC in charming Cavendish
Interior

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

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (17 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
$204 nightly
The price is $230
Sep 3 - Sep 4
Total with taxes and fees
Addie's Place: A Quiet and Quirky Guesthouse
Interior

7. Upscale Cabin 1: hot-tub, private firepit, complimentary kayaks + paddleboards!

Upscale Cabin 1: hot-tub, private firepit, complimentary kayaks + paddleboards!
Cavendish
10.0 out of 10, Exceptional, (19 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.
$330 nightly
The price is $353
Sep 2 - Sep 3
Total with taxes and fees
Upscale Cabin 1: hot-tub, private firepit, complimentary kayaks + paddleboards!
TV, DVD player

8. 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)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
$205 nightly
The price is $232
Sep 2 - Sep 3
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
1 bedroom, desk, iron/ironing board, WiFi

9. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
$206 nightly
The price is $231
Sep 2 - Sep 3
Total with taxes and fees
Bridgewater Living - Ski VT Suite
Property grounds

10. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
$383 nightly
The price is $416
Sep 28 - Sep 29
Total with taxes and fees
Lakefront Family Fun Retreat
Property grounds

11. 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)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
$236 nightly
The price is $266
Sep 2 - Sep 3
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Exterior

12. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
$280 nightly
The price is $316
Sep 2 - Sep 3
Total with taxes and fees
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Interior

13. Perfect Getaway! Cozy, Modern & Convenience to Everything!

Perfect Getaway! Cozy, Modern & Convenience to Everything!
Ludlow
9.8 out of 10, Exceptional, (87 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.
$160 nightly
The price is $181
Sep 17 - Sep 18
Total with taxes and fees
Perfect Getaway! Cozy, Modern & Convenience to Everything!
TV

14. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
$383 nightly
The price is $433
Sep 2 - Sep 3
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Coffee/tea maker, fridge, microwave, oven

15. Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee

Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Sunapee
10.0 out of 10, Exceptional, (58 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
United States
Andrew W.
$388 nightly
The price is $421
Sep 2 - Sep 3
Total with taxes and fees
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Exterior

16. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (171 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
$331 nightly
The price is $371
Sep 2 - Sep 3
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Golf

17. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
$205 nightly
The price is $232
Sep 2 - Sep 3
Total with taxes and fees
Efficient condo near slopes with kitchenette & great location
Exterior

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

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
$240 nightly
The price is $271
Sep 2 - Sep 3
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Exterior

19. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
$211 nightly
The price is $239
Sep 2 - Sep 3
Total with taxes and fees
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Aerial view

20. 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
$210 nightly
The price is $231
Sep 16 - Sep 17
Total with taxes and fees
Mountain Green
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

On The River Inn

On The River Inn

10/10 Excellent
"We had a wonderful stay at On the River. The room was large, clean, and very quiet. It's a short, quick drive into town. The staff was pleasant and helpful. A good choice when staying near Woodstock."
Marc 1-night trip
Posted 2 hours ago
On The River Inn

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 $230 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?

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.