Holiday Homes in Windsor County

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Featured Holiday Homes in Windsor County

Our top choices for Windsor County holiday homes

"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!"

"Charming, comfortable, beautiful place. Felt like home and was everything you could want from a converted barn in Vermont!"

"Gorgeous log home , spacious, cozy , fun and comfortable ."

"Beautiful area and gorgeous leaves. Liked having a weber grill."

"Very cozy, great kitchen. The beds are extremely comfortable. The surrounding area is beautiful with plenty to do. Highly recommend."

"Arturo and John are incredibly thoughtful and attentive hosts. They have considered every possible need and detail in the space. It’s beautiful, homey, and full of personality. The hot tub is a dream. We loved the location. It was easily to get to Woodstock, restaurants, and sightseeing, while still feeling remote and secluded. 10/10 would stay here again! "

"Cozy accommodations, great location, beautiful property, wonderful hosts."

"Wonderful House - Held 2 Families Perfectly3 min drive to mountain The hot tub is great addition "

"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."

"Our annual trip was great! The house was fantastic and the owners were very friendly and responsive. Would definitely recommend this awesome house!"

"Terrific and comfortable place to stay! Amazing firepit!"

"Great property, cozy and well maintained!"

"This place was great for my family and I. It is very close to Okemo and town "

"Nice rental for our family and the owner was very rsponsive."

"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!"

"Great location, cute condo, comfortable beds, modern kitchen."

"Our family had a great stay in Ludlow for a four day ski vacation. Tom and Patti were great hosts and their home is convenient to both Okemo and Killington. The hosts communicated well with us and their place was perfect for our needs (family of 4), clean, and convenient to downtown Ludlow and restaurants. "