Book Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

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
Book a stay at this family-friendly vacation home in Ludlow. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and ...
Opens in a new windowTraveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
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
Stay at this vacation home in Ludlow. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Okemo Mountain Resort and Sachem ...
Opens in a new windowClassic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Quiet Modern Luxury Home w/  Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Bridgewater
Stay at this vacation home in Bridgewater Corners. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Long Trail Brewing Company and Coolidge ...
Opens in a new windowQuiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
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Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
77 Okemo Ridge Rd, Ludlow, VT
Stay at this 3.5-star vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and ...
Opens in a new windowOkemo Mountain Lodging
Beautifully renovated with fireplace and coffee bar

Beautifully renovated with fireplace and coffee bar

Hartford
Book a stay at this golf vacation home in White River Junction. Enjoy free WiFi, a fitness center, and a garden. Popular attractions The Strong House Spa and ...
Opens in a new windowBeautifully renovated with fireplace and coffee bar
Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

Ludlow
Book a stay at this ski vacation home in Ludlow. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and Sunshine Ski ...
Opens in a new windowClassic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Killington
Book a stay at this family-friendly vacation home in Killington. Enjoy free WiFi, a sauna, and a garden. Popular attractions Killington Resort and Fire Tower ...
Opens in a new windowSpacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat

Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat

2 out of 5
Newbury, NH
Stay at this vacation home in Newbury. Enjoy free WiFi, laundry facilities, and in-room jetted tubs. Popular attractions John Hay National Wildlife Refuge and ...
Opens in a new windowSpacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington
Book a stay at this ski vacation home in Killington. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Killington Resort and Sunrise ...
Opens in a new windowSki-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
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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.

Windsor Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Windsor vacation homes are the perfect way for you to wing it.

Holiday houses in Windsor let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Windsor in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Windsor adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Windsor with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Windsor vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Windsor Holiday Homes essential information

Accommodation
762 Holiday Homes
Lowest Price
NZ$253
Highest Price
NZ$697
Popular accommodation
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen, Okemo Mountain Lodging, Beautifully renovated with fireplace and coffee bar, Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table, Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking, Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat, Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Top trending hotels in Windsor

Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

3 out of 5
122 Best Rd, Windsor, VT
Stay at this 3-star farm stay in Windsor. Enjoy free WiFi, free parking, and a garden. Popular attractions Hartland Public Library and Path of Life Garden are ...
Opens in a new windowFat Sheep Farm & Cabins
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is NZ$253 per night from 17 Nov to 18 Nov
NZ$253
17 Nov - 18 Nov
includes taxes & fees
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
Opens in a new windowKillington Mountain Lodge, Tapestry Collection by Hilton
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is NZ$697 per night from 30 Nov to 1 Dec
NZ$697
30 Nov - 1 Dec
includes taxes & fees
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowWoodstock Inn & Resort
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White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
Opens in a new windowWhite River Inn and Suites
Don't see what you're looking for?
See all available properties in Windsor
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.