Photo by mike dobias

Windsor Holiday Rentals

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Check prices for these dates

Tonight
13 Dec - 14 Dec
Tomorrow
14 Dec - 15 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Our top choices for Windsor holiday rentals

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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
Killington
9.0 out of 10, Wonderful, (53)
"Clean and beautiful scenery "
United States
David
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Indoor pool
Mountain Green

Mountain Green

Mountain Green
2.0 star property
Killington
7.0 out of 10, Good, (15)
"Great communication from Jeff."
United States
Dennis
The price is HK$1,726
HK$2,316 total
includes taxes & fees
15 Dec - 16 Dec
Mountain Green
Interior
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
2.0 star property
Killington
The price is HK$1,230
HK$3,096 total
includes taxes & fees
5 Jan - 6 Jan 2026
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
Property grounds
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is HK$654
HK$2,239 total
includes taxes & fees
16 Dec - 17 Dec
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
3 bedrooms, Internet, bed sheets
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

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

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Andover
9.0 out of 10, Wonderful, (29)
"Really nice house in a beautiful place. We had a great time. Plenty of space with multiple bedrooms and bathrooms are great. Great kitchen and grill made it easy to feed lots of people. Also lots of great things to do in the house already. One criticism for me was the screen doors. They were not all set in the rails and some of them had holes that let bugs in. It got a bit warm in the house during the day time with no air conditioning so it would’ve been better if the screen doors were...
United States
Dan T.
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
TV, fireplace, DVD player, books
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE
Killington
9.6 out of 10, Exceptional, (92)
"This condo provided everything we needed for a nice stay of skiing. We very much enjoyed our stay."
United States
Shawn C.
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE
Indoor pool
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

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

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Killington
8.2 out of 10, Very good, (38)
"Room was constantly too hot. Otherwise a great stay"
United States
Cameron M.
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Smart TV, fireplace, video games, DVD player
The Cabin that brings people together

The Cabin that brings people together

The Cabin that brings people together
Bridgewater
9.6 out of 10, Exceptional, (82)
"This was our 3rd visit for an annual family reunion. Nice house with great space, and the yard is a great space to really spread out. The manager is very responsive and checks in periodically; they really want you to have a great stay. I highly recommend this vacation rental, and we’ll be back!"
United States
Peter L.
The Cabin that brings people together
Fridge, microwave, oven, stovetop
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

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

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Ludlow
8.0 out of 10, Very good, (41)
"Plenty of space and the two living rooms are great because the upstairs living room is very small."
United States
Brad H.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Exterior
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
killington
9.6 out of 10, Exceptional, (17)
"Great place to stay. Central location, bedrooms spacious and common areas w/plenty of space to hang out."
United States
Scott B.
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
Exterior
Killington Retreat

Killington Retreat

Killington Retreat
2.0 star property
Killington
9.8 out of 10, Exceptional, (17)
"It was clean and check-in was simple. "
United States
David M.
Killington Retreat
Exterior
Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger

Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger

Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger
West Windsor
Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger
Interior
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (31)
"Very nice property. Full of extra touches (hot tub, virtual fireplace). I appreciated access to a laundry facility. Highly recommend this property."
United States
Julie C.
The price is HK$1,681
HK$2,806 total
includes taxes & fees
14 Dec - 15 Dec
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Exterior
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

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

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Ludlow
9.6 out of 10, Exceptional, (129)
"Beautiful place! Enjoyed our stay!"
United States
Cathy B.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Internet, bed sheets
Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (32)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
United States
C A.
The price is HK$1,082
HK$2,231 total
includes taxes & fees
5 Jan - 6 Jan 2026
Efficient condo near slopes with kitchenette & great location
Dining
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Ludlow
9.4 out of 10, Exceptional, (41)
"Lovely property and great location to outdoor activities."
United States
Ellen C.
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Exterior
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

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

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Ludlow
9.8 out of 10, Exceptional, (181)
"Great stay, for a golf trip with 12 guys, there was plenty of room for everyone, would definitely recommend and will be trying to come back and stay as well!"
United States
Matt C.
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Exterior
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

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

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Ludlow
9.6 out of 10, Exceptional, (19)
"The house, its location, and dock are real nice. Would come here again."
United States
Wendy G.
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Smart TV, fireplace, books
Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock

Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock

Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock
Hartford
10.0 out of 10, Exceptional, (131)
"My sister and I stayed here while taking a two day class at King Arthur Baking School. The pictures don't even do it justice on how cute and well appointed the property is. The beds were very comfortable with nice linens and there were plenty of bath towels. The owners were always quick to respond to any question. We would definitely stay there again. "
United States
Stacy S.
Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock
Property grounds
Treehouse at Wise Pines- SoBo

Treehouse at Wise Pines- SoBo

Treehouse at Wise Pines- SoBo
Woodstock
9.8 out of 10, Exceptional, (24)
"What a unique experience staying in a literal tree house. The bathroom shared with the other tree house was so wonderfully built as is the barn that it resides in. I only stayed one night and wished I stayed multiple nights. I will definitely consider staying here again for future MTB trips in the area! "
United States
Taku S.
The price is HK$1,167
HK$1,455 total
includes taxes & fees
16 Dec - 17 Dec
Treehouse at Wise Pines- SoBo
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

Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon

10/10 Excellent
"Large and clean rooms. This is a remote mountain valley town so it’s expected to not have much around. There is a rock climbing gym next to the hotel though. "
Jianguo 5-night trip
Posted 2 days ago
Hilton Garden Inn Hanover 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 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?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This holiday home rental outside of Windsor is located on the waterfront, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Windsor?

With 12 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.