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Windsor Vacation Rentals

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Check prices for these dates

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Aug 14 - Aug 15
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Aug 15 - Aug 16
This weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24

Vacation Rentals in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (47)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Mountain Green
Indoor pool

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 ￥26,533
￥35,592 total
includes taxes & fees
Aug 17 - Aug 18
Mountain Green
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Fridge, microwave, oven, stovetop

Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

9.0 out of 10, Wonderful, (43)
"My favorite place to stay in the area. Love it! "
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Solitude Village at Okemo
Solitude Village Two Bedroom Suite Mountainside | Private kitchen | Fridge, microwave, stovetop, toaster

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very Good, (26)
"Beautiful Area. "
Solitude Village at Okemo
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Desk, free WiFi, bed sheets

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (54)
"There were dead bugs in the bathroom sink and bath, but it's fairly easy to clean them. Everything else in the room is great!"
The price is ￥12,590
￥25,044 total
includes taxes & fees
Aug 20 - Aug 21
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Indoor pool

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

8.0 out of 10, Very Good, (35)
"Convenient for skiing and visiting the greater VT area. Unit has what you need for your stay."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
3 bedrooms, internet, bed sheets

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

9.0 out of 10, Wonderful, (26)
"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
Converted Carriage Barn | The Carriage House Unit1
Dining

Converted Carriage Barn | The Carriage House Unit1

9.8 out of 10, Exceptional, (20)
"Charming, comfortable, beautiful place. Felt like home and was everything you could want from a converted barn in Vermont!"
Converted Carriage Barn | The Carriage House Unit1
Treehouse at Wise Pines- NoBo
Exterior

Treehouse at Wise Pines- NoBo

9.8 out of 10, Exceptional, (11)
"Unique settings. Loved the accommodations "
The price is ￥24,296
￥30,441 total
includes taxes & fees
Aug 19 - Aug 20
Treehouse at Wise Pines- NoBo
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Exterior

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

9.8 out of 10, Exceptional, (17)
"We loved the house and especially the location. The views are beautiful and the proximity to town, the mountain and parks make it a fantastic spot to stay."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Exterior

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (174)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Beautifully renovated with fireplace and coffee bar
Smart TV, fireplace, books

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (114)
"Very cozy, great kitchen. The beds are extremely comfortable. The surrounding area is beautiful with plenty to do. Highly recommend."
Beautifully renovated with fireplace and coffee bar
Treehouse at Wise Pines- SoBo
Property grounds

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (21)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
The price is ￥24,296
￥30,276 total
includes taxes & fees
Aug 17 - Aug 18
Treehouse at Wise Pines- SoBo
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Interior

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

10.0 out of 10, Exceptional, (20)
"Thanks for a great stay!"
The price is ￥29,156
￥49,965 total
includes taxes & fees
Sep 8 - Sep 9
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Killington Farmhouse-Mountain Biking, Golf, Hiking
Smart TV, video games

Killington Farmhouse-Mountain Biking, Golf, Hiking

10.0 out of 10, Exceptional, (3)
"We visited in the summer…Spacious with room to spread out. Clean with all the things you need. Good communication. Laundry area a little spooky but great working laundry area."
Killington Farmhouse-Mountain Biking, Golf, Hiking
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

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

9.0 out of 10, Wonderful, (72)
"Perfect location for a quick ski trip. "
The price is ￥11,044
￥37,464 total
includes taxes & fees
Aug 18 - Aug 19
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Quaint lakefront home with a fire pit and beautiful views
Property grounds

Quaint lakefront home with a fire pit and beautiful views

9.4 out of 10, Exceptional, (96)
"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 fire pit and beautiful views
Okemo Mountain Lodging
Exterior

Okemo Mountain Lodging

3.5 star property
7.8 out of 10, Good, (28)
"We are so impressed with the lodging. We will definitely be back. "
Okemo Mountain Lodging
Charming Lake Sunapee & Mt. Sunapee Ski Cabin
Exterior

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
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (160)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is ￥25,033
￥53,929 total
includes taxes & fees
Aug 19 - Aug 20
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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

White River Inn and Suites

White River Inn and Suites

10/10 Excellent
"The staff was the best part of this stay. They were friendly and welcoming. The room was very spacious and comfortable for the price."
Michelle 1-night trip
Posted 15 hours ago
White River Inn and Suites

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we offer vacation rentals in Windsor close to Path of Life Garden, 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?

Converted Carriage Barn | The Carriage House Unit1: You might want to consider this vacation rental near Windsor, which is located in a rural location and has a fireplace, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Windsor?

With 9 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 Path of Life Garden 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 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.