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Windsor Vacation Rentals

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Check prices for these dates

Tonight
Dec 23 - Dec 24
Tomorrow
Dec 24 - Dec 25
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Windsor vacation rentals

Comfort Townhome | Private kitchen | Full-size fridge, microwave, oven, stovetop
Brook Road Condo

Vacation Home in Goshen

Brook Road Condo
3.0 star property
8.8 out of 10, Excellent, (3)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is ￥28,870
￥46,986 total
includes taxes & fees
Dec 24 - Dec 25
Brook Road Condo
Fridge, microwave, oven, stovetop
Brook Road Cabin

Cabin in Goshen

Brook Road Cabin
9.8 out of 10, Exceptional, (17)
"Would go back!"
United States
Elizabeth C.
The price is ￥26,673
￥50,730 total
includes taxes & fees
Dec 24 - Dec 25
Brook Road Cabin
Property grounds
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Condo in Clock Tower Base Area

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is ￥18,514
￥52,604 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Apartment in Killington

Clean & bright condo with mountain views & modern kitchen - walk to lifts
7.2 out of 10, Good, (44)
"Quick trip to and from Killington mt"
United States
Phillip F.
The price is ￥14,435
￥47,007 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Exterior detail
Ben & Jerry’s Studio | 10 Min to Killington

Apartment in Bridgewater

Ben & Jerry’s Studio | 10 Min to Killington
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is ￥17,887
￥36,892 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Ben & Jerry’s Studio | 10 Min to Killington
Dining
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

Vacation Home in Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
2.0 star property
10.0 out of 10, Exceptional, (18)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
The price is ￥45,893
￥94,397 total
includes taxes & fees
Dec 30 - Dec 31
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Exterior
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Condo in Cavendish

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
The price is ￥47,070
￥84,701 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Microwave, oven, stovetop, dishwasher
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Condo in Ludlow

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is ￥29,968
￥55,684 total
includes taxes & fees
Jan 12 - Jan 13, 2026
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Indoor pool
Cozy condo on ski shuttle route with free WiFi & full ktichen

Condo in Killington

Cozy condo on ski shuttle route with free WiFi & full ktichen
8.4 out of 10, Very Good, (38)
"Great place. Met our needs. "
United States
Sean K.
The price is ￥18,357
￥52,624 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Cozy condo on ski shuttle route with free WiFi & full ktichen
Exterior
Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Vacation Home in Newbury

Unique Treehouse Near Mt Sunapee – No Cleaning Fee
10.0 out of 10, Exceptional, (26)
"Great stay. Had a wonderful time."
United States
Chris P.
The price is ￥42,363
￥75,927 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Unique Treehouse Near Mt Sunapee – No Cleaning Fee
Exterior
Brook Road Cabin

Cottage in Goshen

Brook Road Cabin
3.5 star property
7.8 out of 10, Good, (9)
"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
Brook Road Cabin
Golf
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Apartment in Ludlow

Well-appointed studio right downtown - less than a mile to Okemo Mountain
8.6 out of 10, Excellent, (12)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
The price is ￥19,769
￥55,955 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Interior
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Condo in Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
9.6 out of 10, Exceptional, (4)
"The place was clean and easy to get to. "
United States
Sarah Z.
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Interior
Addie's Place: A Quiet and Quirky Private Guesthouse

Cottage in Hartford

Addie's Place: A Quiet and Quirky Private Guesthouse
10.0 out of 10, Exceptional, (4)
"Perfect size and location! "
United States
Lyn H.
The price is ￥16,945
￥31,913 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Addie's Place: A Quiet and Quirky Private Guesthouse
Indoor pool, a heated pool
Modern Mountain Condo with Spa

Condo in The Woods

Modern Mountain Condo with Spa
9.6 out of 10, Exceptional, (9)
"The property met our expectations. Great property for parties less than 6 people."
United States
Michael H.
Modern Mountain Condo with Spa
Beach
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Chalet in Plymouth

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
2.0 star property
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is ￥31,631
￥90,781 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Fridge, microwave, oven, stovetop
Chic Farmhouse Decor | Deck w/View

Vacation Home in Sunapee

Chic Farmhouse Decor | Deck w/View
10.0 out of 10, Exceptional, (51)
"This place is pristine and very cozy. Bed's are insanely comfortable too. Will definitely try to stay there again. "
United States
Peter S.
The price is ￥34,518
￥71,499 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Chic Farmhouse Decor | Deck w/View
Exterior
Treehouse at Wise Pines- NoBo

Cabin in Woodstock

Treehouse at Wise Pines- NoBo
9.8 out of 10, Exceptional, (14)
"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "
United States
Ethan
The price is ￥23,535
￥29,343 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Treehouse at Wise Pines- NoBo
Private kitchen
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Cabin in Newbury

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
10.0 out of 10, Exceptional, (16)
"Loved staying at this quaint cottage, the outside spaces were lovely and it was very clean! Communication with the owner was seamless and they were fantastic to deal with. I would highly recommend a stay here! "
United States
Lisa P.
The price is ￥29,654
￥69,968 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Interior
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Condo in Ludlow

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
9.0 out of 10, Wonderful, (22)
"Great rate for a place with all the basics!"
United States
Macgregor
The price is ￥21,025
￥48,680 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
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

Courtyard by Marriott Hanover Lebanon

Courtyard by Marriott Hanover Lebanon

10/10 Excellent
"Therese the front desk manager was excellent. She was so helpful and met our needs. We were so glad she was there."
ilene 1-night trip
Posted 21 hours ago
Courtyard by Marriott 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 vacation rental in Windsor?

Yes, we offer vacation rentals in Windsor close to The Sustainable Farmer, 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?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: You might want to consider this vacation home rental near Windsor, which is located on the waterfront and has a balcony, a garden, 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. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Windsor?

With 12 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 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 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.