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Compare 102 Vacation Homes in Winchester with updated reviews, rates, and availability.

Plenty of private open space to explore with the whole family!

"We loved this property with stunning foliage, hiking trails, and perfect views. The house had everything we needed to accommodate a large group and more with lots of thoughtful touches. Plenty of space, panoramic views, screened in porch, fireplace, pool table, and connected speakers throughout. We have stayed at many different rentals for our annual trip over the years and this one is our new favorite."

"This is our 3rd time staying here, we love this historic home, it is in very good condition. The home is very clean, well stocked, the layout is very good and the communication with the host is also very good. We love the brook going by. It is close to Smith College where our daughter goes to school. We also enjoy the many other places and things to do in this area. Even after our daughter graduates I can see us coming back to this home and part of Massachusetts. "

"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...

"Every need accommodated including a back-up generator! Well appointed kitchen and bathrooms. Very cozy and spacious home inside. Very comfortable bed mattress in master bedroom. Lots of yard for dogs to run free. Nature all around. Lots of books and board games there. Laundry room was a big plus. Remote setting but lots to see and explore within reach. Very lovely stay and hosts were very responsive."

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

SAR 822 total

includes taxes & fees

24 Nov - 25 Nov

"Melanie, our host, was great throughout our whole stay. The check-in process was very easy! There were great recommendations of places to go while in town. The location is amazing, great views of the picturesque river, very easy quick walk into town, everything you need with in walking distance. The apartment/cabin itself is beautiful. There is a fully equipped kitchen. The living room is perfect for snuggling on the couch. The bed was very comfortable and linens were soft. The bathroom was also...

"The property was beautiful--great views, super peaceful, and fabulous hosts. "

SAR 1,287 total

includes taxes & fees

24 Nov - 25 Nov

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...

"We stayed three nights here. Just the two of us. I felt the pictures were misleading. Much smaller than expected. Since it was just the two of us it was perfect. "

"This property is really “in the “woods” We enjoyed our stay, so peaceful. The foliage was beautiful. There was a lot of DVD’S to watch, no cable or regular channels. There was also a record player with many albums to choose from. Comfortable mattresses and pillows. Very well equipped with everything you need to prepare a meal at the house. River Bend Farm Market is about 15 minutes away and it has ready to go food, sandwiches, everything you need to find at a grocery store. Great communication...

"House was large and comfortable with space for everyone. Enjoyed dinners with our group around the dining table. Kitchen is older but works. Played a charades-type game in the living room one evening. Peterborough wonderful for eats, walking and shopping. "

"Nice relaxing time spent with my family skiing at Mount Snow. Only complaint would be the high fees associated with the property compared to others."

"We had an amazing week at the Tyler House. The house and location are among the best on the lake. The host lives nearby and is happy to assist with any requests."

"Very nice home, quiet location, and house had everything we needed and more. Property manager timely communicated all necessary information."

"What a fun place to stay. Highly recommend for weekend away with kids. So much room for everyone to relax after skiing. Great location to mountain. Very clean and owner was so easy to get in touch with. Definitely will be back next year!!"

"Loved the location and property. Easy to work with Anthony very responsive"

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

"This place was SO fun to stay at, and we did not have enough time during our 3 night stay to experience it all! The house is clean, the grounds are beautiful and scenic, and the location is near so many fun places to go. The amount of activities at the house alone gives you more than enough entertainment that you never even have to go explore, but the whole area is equally wonderful. The host was very communicative and helpful. Thank you for everything we hope to be back next year!"

"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!"