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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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
The price is SAR 790
SAR 1,066 total
includes taxes & fees
22 Oct - 23 Oct
Fat Sheep Farm & Cabins
Beach

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 SAR 1,048
SAR 1,854 total
includes taxes & fees
29 Sep - 30 Sep
Cabin on the hill Ascutney Vt - 4 bedrooms
Exterior detail

3. 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, (54 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 SAR 927
SAR 1,654 total
includes taxes & fees
29 Sep - 30 Sep
Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
Interior

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 SAR 479
SAR 838 total
includes taxes & fees
28 Sep - 29 Sep
Addie's Place: A Quiet and Quirky Guesthouse
Interior

5. 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.
The price is SAR 1,057
SAR 1,907 total
includes taxes & fees
28 Sep - 29 Sep
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
Smart TV, fireplace, DVD player, books

6. 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.
The price is SAR 894
SAR 1,606 total
includes taxes & fees
28 Sep - 29 Sep
Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards
Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix

7. 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 SAR 689
SAR 1,123 total
includes taxes & fees
29 Sep - 30 Sep
Brook Road Cabin
Exterior

8. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (5 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is SAR 2,024
SAR 3,537 total
includes taxes & fees
28 Sep - 29 Sep
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Smart TV, fireplace, DVD player, books

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

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is SAR 818
SAR 1,519 total
includes taxes & fees
20 Oct - 21 Oct
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Exterior

10. Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.6 out of 10, Exceptional, (27 reviews)
"Amazing weekend stay with our pup! Looking forward to staying here in the summer! "
United States
Naydene G.
The price is SAR 845
SAR 1,519 total
includes taxes & fees
4 Oct - 5 Oct
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Outdoor pool, a heated pool

11. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (24 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
The price is SAR 1,126
SAR 1,909 total
includes taxes & fees
29 Sep - 30 Sep
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
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
The price is SAR 676
SAR 1,129 total
includes taxes & fees
29 Sep - 30 Sep
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Dining

13. Gorgeous, clean studio in brand new building.

Gorgeous, clean studio in brand new building.
Hartford
The price is SAR 469
SAR 764 total
includes taxes & fees
4 Oct - 5 Oct
Gorgeous, clean studio in brand new building.
Indoor pool

14. Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (64 reviews)
"The host is extremely friendly and accommodating! The place is large and didn’t feel cramped with two adults and five male teenagers! Perfect in every way, clean, well stocked, and easy access to the slopes!"
United States
Nina
The price is SAR 1,877
SAR 3,186 total
includes taxes & fees
28 Sep - 29 Sep
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
TV

15. 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 SAR 690
SAR 1,784 total
includes taxes & fees
28 Sep - 29 Sep
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Exterior

16. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is SAR 791
SAR 2,959 total
includes taxes & fees
28 Sep - 29 Sep
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Smart TV, fireplace, video games, books

17. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is SAR 558
SAR 1,810 total
includes taxes & fees
28 Sep - 29 Sep
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
TV, fireplace, computer monitors

18. Elysium on Little Sunapee-Dock, Firepit, Trails

Elysium on Little Sunapee-Dock, Firepit, Trails
New London
9.8 out of 10, Exceptional, (18 reviews)
"We had a wonderful time at the lake. The house was perfect for our family as we were all able to gather together and then retreat to our own sleeping spaces. The check in process was easy and communication was great. We also got a chance to try paddle boarding! Will definitely be returning."
United States
Julie C.
The price is SAR 1,215
SAR 3,253 total
includes taxes & fees
28 Sep - 29 Sep
Elysium on Little Sunapee-Dock, Firepit, Trails
Smart TV, video games, books

19. Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
Sunapee
9.8 out of 10, Exceptional, (11 reviews)
"Great stay, the boys will be back! "
United States
Susan B.
The price is SAR 1,502
SAR 2,595 total
includes taxes & fees
4 Oct - 5 Oct
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
TV, fireplace, books

20. @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 SAR 659
SAR 2,104 total
includes taxes & fees
5 Oct - 6 Oct
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. 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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
":)"
Nicholas 2-night trip
Posted 3 hours ago
The Mountain Inn at Killington

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.