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Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (163)
"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

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (38)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

Converted Carriage Barn | The Carriage House Unit1

9.8 out of 10, Exceptional, (21)
"Charming, comfortable, beautiful place. Felt like home and was everything you could want from a converted barn in Vermont!"
Converted Carriage Barn | The Carriage House Unit1

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

9.8 out of 10, Exceptional, (174)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Custom-built Tiny House on forested lot near Quechee

9.8 out of 10, Exceptional, (60)
"Small and cozy"
Custom-built Tiny House on forested lot near Quechee

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

2.0 star property
9.8 out of 10, Exceptional, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (114)
"Very cozy, great kitchen. The beds are extremely comfortable. The surrounding area is beautiful with plenty to do. Highly recommend."
Beautifully renovated with fireplace and coffee bar

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (54)
"Margarete and Alice welcomed us upon arrival. The house was the quintessential New England home! It was super clean, our bed was very comfortable with soft welcoming linens. The views are incredible, and the property provided much needed peace and tranquility. The weather was not the best but we managed to find plenty to do in the area. Alice, Margarete's black lab, took us for a hike on the property. She was an excellent playful guide! We look forward to returning to this peaceful retreat in...
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Ski Chalet with Hot Tub on Okemo Mountain

10.0 out of 10, Exceptional, (44)
"Wonderful House - Held 2 Families Perfectly3 min drive to mountain The hot tub is great addition "
Ski Chalet with Hot Tub on Okemo Mountain

Converted Carriage Barn | The Carriage House Unit2

9.6 out of 10, Exceptional, (4)
"Very cool conversion of an old barn. Very comfy and rather iconic. Because of the barn construction, there was an occasional encounter with a bug or two. Nicely located with many shops and restaurants nearby. The surrounding neighborhood of Quechee is very pleasant and kind of upscale country. Be aware there are no hangers/closets/ironing board/washer/dryer, so plan accordingly."
Converted Carriage Barn | The Carriage House Unit2

Studio Suite #9 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

10.0 out of 10, Exceptional, (28)
"The cabin was perfect. Had everything we might need. Loved the room, views, location, and game room. Thanks so much "
The price is AU$374
includes taxes & fees
2 Sept - 3 Sept
Studio Suite #9 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

104 Two Queen Bed Standard Hotel Room outdoor heated pool

8.6 out of 10, Excellent, (27)
"Excellent customer service and beautiful, well-maintained property."
The price is AU$247
includes taxes & fees
24 Aug - 25 Aug
104 Two Queen Bed Standard Hotel Room outdoor heated pool

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

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

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"Absolutely loved it!!! Amazing house. Will definitely stay again!"
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

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

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

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

9.8 out of 10, Exceptional, (37)
"Great property, cozy and well maintained!"
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

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

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

10.0 out of 10, Exceptional, (109)
"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

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (220)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
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