Photo by William E Berry Jr.

Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

9.0 out of 10, Wonderful, (25)
"Had a great stay, cozy log cabin, beds were very comfortable. So nice to have a few garbage bags, paper towels, soaps and toiletries!! Also some coffee filters:) Hot tub was great too! "
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (43)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (209)
"Location was perfect. Cabin cute and comfortable. Pond was an amazing bonus with lots of cool birds. We had the best vacation there ever!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Addie's Place: A Quiet and Quirky Private Guesthouse

The price is €218
includes taxes & fees
30 Jun - 1 Jul
Addie's Place: A Quiet and Quirky Private Guesthouse

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (108)
"Our stay was terrific! Such a lovely renovated home! "
Beautifully renovated with fireplace and coffee bar

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (157)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is €320
includes taxes & fees
30 Jun - 1 Jul
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Lake Sunapee & Mt. Sunapee Ski Cabin

9.6 out of 10, Exceptional, (23)
"Great get away on lake Sunapee, great house just a short walk to the lake. Great place to relax and take in the sun set on the dock or grilling on the deck. Well equipped home that is super clean,just a great getaway. "
Charming Lake Sunapee & Mt. Sunapee Ski Cabin

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

10.0 out of 10, Exceptional, (17)
"Thanks for a great stay!"
The price is €272
includes taxes & fees
1 Jul - 2 Jul
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (9)
"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
The price is €392
includes taxes & fees
1 Jul - 2 Jul
Cozy Creekside Chalet centrally located near 4 ski resorts

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (210)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.8 out of 10, Exceptional, (12)
"We loved the location and home! So close to Okemo, beautiful home right on the lake. The hottub and gas fireplace were appreciated after a day of skiing. We would definitely come back again!"
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.0 out of 10, Very good, (38)
"Had a business retreat with 6 associates. The cabin was great and operated as one would expect for a ski cabin. Nice fire place and hot tub. The TVs are older so they have a hard time connecting to the WIFI for Netflix, Prime, etc. I recommend bringing agame console aor "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Quaint lakefront home with a private deck, firepit, and dock

9.4 out of 10, Exceptional, (94)
"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."
Quaint lakefront home with a private deck, firepit, and dock

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

10.0 out of 10, Exceptional, (24)
"A terrific place. Highly recommended. We had a great family ski vacation."
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Custom-built Tiny House on forested lot near Quechee

9.8 out of 10, Exceptional, (57)
"Small and cozy"
Custom-built Tiny House on forested lot near Quechee

Mountain Green

2.0 star property
6.6 out of 10, (10)
"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "
The price is €277
includes taxes & fees
7 Jul - 8 Jul
Mountain Green

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

10.0 out of 10, Exceptional, (88)
"We needed a quiet place to stay in the woods. It was close to Ludlow shops/ restaurants and the Okemo Ski. "
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Treehouse at Wise Pines- NoBo

9.6 out of 10, Exceptional, (9)
"We enjoyed our stay. It was a great place with great people. We had an amazing time there. "
The price is €181
includes taxes & fees
30 Jun - 1 Jul
Treehouse at Wise Pines- NoBo

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

3.0 star property
9.4 out of 10, Exceptional, (10)
"Excellent location"
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.4 out of 10, Very good, (32)
" Convenient location right off Killington Rd. Short drive to ski or restaurants. One bar/restaurant on site- Vermont Craft. Newly renovated studio, clean on arrival. Check-in as described, did not need to contact host during stay. Thorough details provided in pre arrival communications. "
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
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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Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to The Sustainable Farmer, 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?

Okemo Mountain Lodging: This holiday home rental outside Windsor is in the mountains, and equipped with daily housekeeping and an LCD TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

How many holiday rentals are there in Windsor?

With 9 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 lovely local spots to enjoy the outdoors, whereas family-friendly attractions include The Sustainable Farmer. Other places in town to visit include American Precision Museum 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.