Holiday Homes in Windsor County

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Featured Holiday Homes in Windsor County

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (97)
"Excellent house, very clean, has everything you need. The checkin process was very smooth, and the hosts were quick to respond when something wasn't working (only because I had accidentally unplugged it!). They did a great job clearing the snow from the house after the storm and the location/parking/access to Quechee was great! Thank you!"
Beautifully renovated with fireplace and coffee bar

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (202)
"Great place after a long day of skiing. Very close to Jackson Gore base area. The house was clean and communication was spot on. "
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (94)
"Everything was as advertised! Great location and easy to find. "
The price is AU$690
includes taxes & fees
1 Apr - 2 Apr
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo

9.8 out of 10, Exceptional, (38)
"The property is recently renovated so everything is relatively new and in good condition. The unique design choice of using cedar for the walls, floors and ceiling was a bit off putting initially but we got used to it. There was a small issue with the hot tub, but the host responded very quickly and the issue was resolved the next day. Will definitely consider staying here for the next Okemo ski vacation."
Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo

Vermont's Mountain Villa: Hot tub, Ski views, Pet+

10.0 out of 10, Exceptional, (8)
"I love Winter and love to be in the snow and crisp air. The week was perfect for outside adventures and this home was perfect to warm us and nourish our hearts, bellies and spirits. The views at sunrise and sunset are extrodinary. "
Vermont's Mountain Villa: Hot tub, Ski views, Pet+

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

8.0 out of 10, Very good, (2)
" short stay "
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

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

9.6 out of 10, Exceptional, (36)
"The home is as described with plenty of space for my family of 5. The kitchen was well stocked, and the bathrooms were clean. Plenty of towels and the beds were firm with clean sheets. The views of Lake Rescue were beautiful. The driveway was snow-covered, but with a 4WD, you should have no issue. The 'commute' to Okemo was easy - 8min max. The house seems to have been empty, so a musty smell permeated the home for the first day until the air circulated a few times. Not a big deal. The gas...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Townhome with patio & on-site pool, hot tub, sauna & tennis access

10.0 out of 10, Exceptional, (4)
"Clean and convenient "
Townhome with patio & on-site pool, hot tub, sauna & tennis access

Riverfront, family fun, amazing rec room, close to Magic & Okemo

9.8 out of 10, Exceptional, (10)
"We had a great stay here for a quick trip to Okemo, which is about 22 minutes away. House was perfect for our small group and we liked the family room area, although with fresh snow we were all exhausted from skiing and didn’t use it much. The inner breezeway was nice to leave our snow covered and sometimes dirty shoes in which kept the house clean and clear. We would definitely stay here again. Great communication with the host who allowed a late check out. Did at the Scottish pub in Chester...
Riverfront, family fun, amazing rec room, close to Magic & Okemo

Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

10.0 out of 10, Exceptional, (1)
"Was an amazing location with tons to do. Clean property and cozy!"
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.8 out of 10, Excellent, (23)
"Basic ski house, in cool spot. 10 mins from bear mtn. Would definitely stay here again. "
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Historic Rideout 16m to Okemo Walk to Town

10.0 out of 10, Exceptional, (21)
"We were a large group of adults, teens and tweens and this house was perfect for our vacation! There are so many private nooks to have some alone time along with a great open family room and kitchen area to come together. We loved its charm, its coziness and variety of spaces. David was great to work with and very accommodating. Would definitely recommend and book again."
Historic Rideout 16m to Okemo Walk to Town

NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

10.0 out of 10, Exceptional, (35)
"Property was super clean and SO CLOSE to the mountain. Everything was perfect- no complaints! "
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (157)
"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"
Idyllic Lakefront House Suited Two Families

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

8.2 out of 10, Very good, (35)
"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

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

9.8 out of 10, Exceptional, (169)
"Great house for family. Enjoyed our trip. So close to Okemo. "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

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

9.8 out of 10, Exceptional, (119)
"Very nice house very close to Okemo and an easy 30min drive to killington. I admit I was very worried about a snow storm with high winds that might have us snowed in with no power. We had to contact the owner/property manager to get us plowed out and within an hour the driveway was cleared of the 16 inches of snow and off we went to ski Okemo for the day. At no time did we lose power even with 60 MPH winds. The neighbors offered to help us if we needed anything. I would highly recommend staying...
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Slopeside townhome on Okemo Ski Mountain! Summer Pool, Tennis & Air Conditioning

10.0 out of 10, Exceptional, (24)
"Fantastic stay at this wonderfully located condoChad was incredibly communicative and helpfulNarrow spiral staircase to upper and lower levels, doable for our adults and children "
Slopeside townhome on Okemo Ski Mountain! Summer Pool, Tennis & Air Conditioning

Mountainside 5-BR Ski-In/Out Okemo Estate

10.0 out of 10, Exceptional, (7)
"Perfect ski in ski out. Beautiful home with everything you need. Will definitely be going back "
Mountainside 5-BR Ski-In/Out Okemo Estate

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (8)
"Very clean, historic farmhouse. 20 minutes from Okemo. Great host. Very updated kitchen with everything you’d need to cook. Easy in, easy out."
The price is AU$695
includes taxes & fees
26 Mar - 27 Mar
Charming Chester Farmhouse – peaceful and close to everything!
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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