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

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Windsor holiday 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 AU$367
includes taxes & fees
10 Sept - 11 Sept
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
The price is AU$736
includes taxes & fees
10 Sept - 11 Sept
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 #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access

Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access
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.
The price is AU$486
includes taxes & fees
8 Sept - 9 Sept
Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access
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, (18 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is AU$279
includes taxes & fees
8 Sept - 9 Sept
Addie's Place: A Quiet and Quirky Guesthouse
A covered porch with wicker furniture, a table, and chairs.

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.
The price is AU$845
includes taxes & fees
8 Sept - 9 Sept
Terrific 3-bedroom cottage with AC in charming Cavendish
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

6. 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)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
The price is AU$542
includes taxes & fees
15 Sept - 16 Sept
Cozy Chic! Cabin #3: wooded delights with year-round hot-tub and private firepit
A two-story house with a green roof, a covered porch, and a driveway with a parked car.

7. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is AU$317
includes taxes & fees
8 Sept - 9 Sept
Bridgewater Living - Ski VT Suite
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 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.
The price is AU$486
includes taxes & fees
8 Sept - 9 Sept
Upscale Cabin 1: hot-tub, private firepit, complimentary kayaks + paddleboards!
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

9. 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.
The price is AU$326
includes taxes & fees
8 Sept - 9 Sept
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A spacious living area with hardwood flooring, a staircase, a black entertainment unit, a door, and a window with blinds.

10. Explore the upper valley from this spacious Claremont Home

Explore the upper valley from this spacious Claremont Home
Claremont
The price is AU$501
includes taxes & fees
8 Sept - 9 Sept
Explore the upper valley from this spacious Claremont Home
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

11. 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.
The price is AU$570
includes taxes & fees
28 Sept - 29 Sept
Lakefront Family Fun Retreat
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)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
The price is AU$369
includes taxes & fees
8 Sept - 9 Sept
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
A red building with a bear logo, a stone pathway, and neatly trimmed bushes.

13. Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Killington
8.8 out of 10, Excellent, (8 reviews)
"Great room, plenty of amenities, close to restaurants and mountains"
United States
Daniel T.
The price is AU$235
includes taxes & fees
8 Sept - 9 Sept
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
A spacious living room with a fireplace, large windows, and a cozy seating area.

14. @SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Sunapee
10.0 out of 10, Exceptional, (26 reviews)
"The perfect winter stay for our family! Perfect location, close to Mount Sunapee. Gorgeous views and home. Host was extremely welcoming and responsive, and the whole stay was easy."
United States
Amanda R.
The price is AU$818
includes taxes & fees
16 Sept - 17 Sept
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
A white building with a porch, a signboard, and a road with a white fence in the background.

15. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
The price is AU$325
includes taxes & fees
8 Sept - 9 Sept
Bridgewater Living - Ben&Jerry Suite
A modern living room with a fireplace, a television, and a ceiling fan.

16. 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.
The price is AU$589
includes taxes & fees
8 Sept - 9 Sept
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
A cabin with a large, curved roof and a smaller adjacent structure, surrounded by dense forest and mountains in the background.

17. 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
The price is AU$439
includes taxes & fees
8 Sept - 9 Sept
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
A red house with a covered porch and a chimney.

18. 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, (172 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.
The price is AU$505
includes taxes & fees
8 Sept - 9 Sept
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A spacious living room with a stone fireplace, wooden furniture, and large windows.

19. 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.
The price is AU$971
includes taxes & fees
8 Sept - 9 Sept
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a hanging light fixture.

20. 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.
The price is AU$619
includes taxes & fees
21 Sept - 22 Sept
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
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 Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Bel endroit pour passer du temps avec la famille."
Mariline 2-night trip
Posted 1 hour ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$279 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to Maze of Adventure, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Windsor has to offer?

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock: This holiday home rental outside of Windsor 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 that you can immerse yourself in your holiday.

How many holiday rentals are there in Windsor?

With 11 Expedia holiday rentals, you're guaranteed 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 Mt Ascutney State Park and Harpoon Brewery.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.