Holiday Homes in Windsor County

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Featured Holiday Homes in Windsor County

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (165)
"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

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (115)
"My husband and I came from Michigan and met family from Massachusetts to run the Covered Bridges Half Marathon! This spot was so perfect—we loved the coffee bar and just enjoyed how comfortable and homey the whole place feels. We would stay here again in a heartbeat!"
Beautifully renovated with fireplace and coffee bar

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

8.0 out of 10, Very good, (40)
"This place was great for my family and I. It is very close to Okemo and town "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

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

9.8 out of 10, Exceptional, (126)
"Terrific and comfortable place to stay! Amazing firepit!"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

10.0 out of 10, Exceptional, (6)
"Lovely rustic and cozy cabin stay"
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

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

9.0 out of 10, Wonderful, (26)
"Had a great stay, cozy log cabin, beds were very comfortable. So nice to have a few garbage bags, paper towels, soaps and toiletries!! Also some coffee filters:) Hot tub was great too! "
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

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

9.8 out of 10, Exceptional, (175)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

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

10.0 out of 10, Exceptional, (110)
"Nice rental for our family and the owner was very rsponsive."
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Country townhome - mountain view - walk to Village of Quechee - near Club & golf

9.0 out of 10, Wonderful, (36)
"Great location, cute condo, comfortable beds, modern kitchen."
Country townhome - mountain view - walk to Village of Quechee - near Club & golf

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

9.8 out of 10, Exceptional, (218)
"If your looking for beauty nature and comfort this cozy cottage surpassed our expectations our dog loved the lake and ducks and snow we lived ludlow okemo woodstock and Westin all so close great location and our host was wonderful prompt response with any questions and added a night last minute for us thanks so much Kristin "
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

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

10.0 out of 10, Exceptional, (36)
"Our annual trip was great! The house was fantastic and the owners were very friendly and responsive. Would definitely recommend this awesome house!"
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (76)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Premier Woodstock Village Riverfront Home

10.0 out of 10, Exceptional, (1)
"This gorgeous home is an absolute gem. Everything needed was anticipated by these amazing hosts. The setting is magical and there are a variety of outdoor spaces for enjoyment of the grounds. The outdoor porches are just lovely, and so very comfortable.This home is so beautifully constructed and the owners have impeccable taste. Every drawer was orderly, every cooking vessel special. The artwork is beautiful, the beds comfortable, and bathrooms just perfect. Views abound from all windows! Stroll...
Premier Woodstock Village Riverfront Home

Quechee - Four Season Resort Townhome

10.0 out of 10, Exceptional, (10)
"Very nice ski chalet with great kitchen, large and private bedrooms and a hot tub. Very suitable for a small family retreat."
Quechee - Four Season Resort Townhome

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

8.6 out of 10, Excellent, (27)
"The host and house manager are absolutely the best. Felt very taken care of - they went above and beyond."
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

10.0 out of 10, Exceptional, (48)
"Such a lovely place to stay during our ski trip! The place is clean and spacious, right on the lake and close to everything. "
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

Lake Pinneo, Golf View, Hot Tub | Tee Time Retreat

9.6 out of 10, Exceptional, (10)
"The house was super cozy and warm feeling! Great location and very relaxing New England town. "
Lake Pinneo, Golf View, Hot Tub | Tee Time Retreat

RoundTop Chalet- Hot Tub, Grill, Hiking!

RoundTop Chalet- Hot Tub, Grill, Hiking!

The Carol - 10 minutes to Okemo & Newly Renovated

10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
The Carol - 10 minutes to Okemo & Newly Renovated
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 County Hotel Reviews

Find out more about Windsor County

Find out more about Windsor County

Windsor County Holiday Homes information

Number of reviews
Accommodation
500 Holiday Homes
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Highest Price