Photo by William E Berry Jr.

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan

Holiday 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, (51)
"Clean and beautiful scenery "
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, (13)
"Great communication from Jeff."
The price is HK$1,463
HK$1,963 total
includes taxes & fees
13 Oct - 14 Oct
Mountain Green
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 HK$630
HK$1,994 total
includes taxes & fees
13 Oct - 14 Oct
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Fridge, microwave, oven, stovetop

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

8.0 out of 10, Very good, (41)
"This Vrbo has been housing people since the 1960's, and we're so glad to be a part of this place's history It is truly a timeless home within a beautiful area with great outdoor activites, generous people and good food (we recommend The Hatchery). Both showers (the top floor shower and the middle floor) did have a leak, but our hosts responded quickly to our concerns and addressed them within a timely manner :) "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Solitude Village at Okemo
Private kitchen

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very good, (31)
"Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also."
Solitude Village at Okemo
Killington Retreat
Exterior

Killington Retreat

2.0 star property
9.6 out of 10, Exceptional, (13)
"Had a great time staying so close to Killington. Sauna, hot tub and pool were a great way to warm up after a day of skiing."
Killington Retreat
Okemo Mountain Lodging
Exterior

Okemo Mountain Lodging

3.5 star property
7.8 out of 10, Good, (28)
"I had an amazing time with my family, I will definitely be coming back "
Okemo Mountain Lodging
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, (177)
"We had a nice time, thank you. Enjoyed jacuzzi, fire outside and local pizza and waterfalls:) "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Winterplace at Okemo
Property grounds

Winterplace at Okemo

4.0 star property
8.8 out of 10, Excellent, (24)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
Winterplace 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, (55)
"Cozy but all the amenities, great location"
The price is HK$665
HK$1,324 total
includes taxes & fees
20 Oct - 21 Oct
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Exterior

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

9.8 out of 10, Exceptional, (127)
"Terrific and comfortable place to stay! Amazing firepit!"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Beautifully renovated with fireplace and coffee bar
Smart TV, fireplace, books

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (120)
"This place was quite simply brilliant. I stay with my wife and four kids. The kids range in age from 10-17 and we had a great stay exploring the Upper Valley area"
Beautifully renovated with fireplace and coffee bar
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Exterior

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

9.6 out of 10, Exceptional, (18)
"The house, its location, and dock are real nice. Would come here again."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Lake

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

10.0 out of 10, Exceptional, (142)
"Cute cabin close to Okemo and town! Really enjoyed our stay and would definitely return. "
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Idyllic Lakefront House Suited Two Families
Property grounds

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (171)
"We spent 11 nights at the house, everything was great."
Idyllic Lakefront House Suited Two Families
Killington Sapphire
Living area

Killington Sapphire

9.2 out of 10, Wonderful, (7)
"Everything we needed to enjoy your family trip!"
Killington Sapphire
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, (163)
"We very much enjoyed our stay, check in was a breeze and we found the cabin to be a cozy retreat. We have been looking for a place that had a bed and bath on first floor to accommodate some mobility limitations and this home was perfect having a single step on the front porch. We look forward to booking another trip with this host "
The price is HK$1,323
HK$2,877 total
includes taxes & fees
14 Oct - 15 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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, (28)
"We were only 4 people, and it felt huge. The cabin is nice, but does show some aging here and there. Nothing that was an actual issue, though. The property with the pond, the fire pit area and the little playground is absolutely gorgeous, though. The cabin offers plenty of space with 4.5 separate sleeping areas (there is a large futon in the game room that could be used in an emergency, I guess). The livingroom/kitchen area is very spacious with great views. Will definitely consider this for...
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Amazing home on 90 acres - AC, fireplace & great mountain views
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (43)
"Was good older log cabin with decent amenities. Everything worked. family was comfortable. nice area."
Amazing home on 90 acres - AC, fireplace & great mountain views
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
Exterior

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

9.8 out of 10, Exceptional, (37)
"This house was a great setting for a large group of adults and kids; plenty of room to spread out and places for everyone to sleep. Close enough to swimming holes and breweries during the day, and our sunset bonfires had a great view. It was really helpful that essentials were already at the house, and it was clean. Communication with the host was top notch!"
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
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

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

10/10 Excellent
"Great place to stay. Lovely atmosphere. Pool and hot tub were nice. Great hot buffet breakfast. They kept replenishing the hot food which was great. Room was clean. "
Lauren 1-night trip
Posted 2 days ago
Fireside Inn & Suites West Lebanon

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to Path of Life Garden, 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?

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable: This holiday home rental outside of Windsor is located in the city centre, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Windsor?

With 10 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 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 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.