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Compare Vacation Homes in Winchester with updated reviews, rates, and availability.

"We really appreciated the solitude and quiet retreat this cabin offered. "

"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...

"Great house and property. Best great room around! Location is perfect. The owner is very friendly and knowledgeable about the house and location."

Green River Cottage. Walk up ramp to enter patio area, lockbox on inside door.

"It is a beautiful home with a ton of space (we only had 3 people, but it easily sleeps 6), very clean and well-kept. Our hosts provided everything we needed to make our stay perfect. I also like that the hosts were not overboard with all the rules, as with some other rentals. The hosts were beyond friendly and had excellent communication throughout the whole process. If you are looking for a lovely home with a ton of space to stay while exploring Vermont and Massachusetts, I highly recommend...

"My boyfriend and I (and our dog) really enjoyed this place. It’s on a quiet road, tucked up into a woodsy hill which gives the feeling of being secluded, while in actuality not being far from a main road. The listing is pretty accurate; the house is absolutely covered in windows, which allows for plenty of fresh air and natural light. The master bed is super comfortable, and the master bathroom is really nice too. I was a little apprehensive about the lack of air conditioning, but there is a...

"We stayed at the Mountain View for a work field trip. We were celebrating the delivery of several pianos we rebuilt for the Yellow Barn I'm Putney. We spent most of our time outside, but when we came back, it was delightful. This is a beautiful property, very clean, and very cozy"

Royalston Vacation Rental | 4BR | 2BA | Stairs to Access | 3,200 Sq Ft

"Stayed here with my brothers and cousins.. had a great time. Close proximity to Royalston Falls and a great hike through the forest "

A full kitchen with almost everything you need to cook your favorite dishes.

"Beautiful property with great quality towels, furniture, and amenities. Great views and great location. Would be happy to stay again. "

"Second time staying at this property ! Very relaxing, beds super comfortable. Would highly recommend."

Westmoreland Vacation Rental | 3BR | 1BA | 1,620 Sq Ft | Stairs Required

"Easily walkable to the very lovely village of Westmoreland, but secluded and with a beautiful view, really quiet and user-friendly. Attentive property owners checked in with us to make sure everything was okay, which was kind and made us feel at home. A terrific porch that's warm in the sunshine even in winter, with great views of birds, sky and stars. "

"Nice place on a quiet street. Stay went perfect "

AED 751 total

includes taxes & fees

13 Jan - 14 Jan

"House is comfortable and well stocked."

"Beautiful home in a stunning location"

"We very much enjoyed our stay. The people were super friendly and welcoming!"

Dover Vacation Rental | 3BR | 3.5BA | 3 Steps to Access | 2,400 Sq Ft

"Mark and David are very easy and helpful The property is excellent We will come back!"

"My friend and I of many years booked this house. What a wonderful surprise. First of all, the host was very prompt and efficient. The house was very easy to find. OH my god!! The house is absolutely beautiful. So very clean. It has everything that you would ever need. Now ....to the decor. It was exquisite. In such incredible taste. Modern touches yet very refined and very comfortable. One of the most beautiful homes that I have ever stayed in. "

"Very nice house with great amenities ! Beautiful location right on the lake (we may come back for a summer get together!) Highly recommend (just note - there’s plenty of room - but there is only one bed/bedroom)"

"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"