A snow-covered town with a river running through it, surrounded by mountains and trees.

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Aug 11 - Aug 12
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Aug 12 - Aug 13
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Aug 14 - Aug 16
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Top Winchester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Everything was very clean and very well taken care of. The bed was very comfortable the place where I think maybe the stay was lacking was the breakfast, not very exciting. It was adequate and well stocked. I do like that. There was coffee available 24 hours."
Margaret 2-night trip
Posted 3 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The breakfast was great. The staff was very friendly."
Greg 2-night trip
Posted 21 hours ago
Hampton Inn Brattleboro
Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"We went just for a quiet night away and it surpassed my expectations. The cabins were wonderful and there was plenty to do to keep my teenagers entertained."
Juli 1-night trip
Posted 22 hours ago
Vikings Villages Resort
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent
"Perfect!"
Sophie 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent
"Balcony over looking the river. Very relaxing"
Hosea 2-night trip
Posted 1 day ago
Riverside Hotel, an Ascend Collection Hotel
The Inn At Crumpin Fox

The Inn At Crumpin Fox

8/10 Good
"This hotel is a solid option when exploring the northern edges of Western Mass. The air conditioning was fantastic, and in an area where many have none, or are working from window units, this was useful for an August stay. There are no real frills at The Inn, but the water pressure is good and the AC works, so that’s a high recommendation."
Bjorn 3-night trip
Posted 2 days ago
The Inn At Crumpin Fox
Windmill Motel Restaurant

Windmill Motel Restaurant

10/10 Excellent
"I love the outdoor seating area with the tent and outdoor couches and I love the colors and textures used for the room I stayed in. When I checked in, I was hot from being at SoulFest and the owners gave me a cloth hand fan for free! When I came home that night, I was hungry and there were chips and chocolates in my room! That was wonderful and thoughtful. They also sell food in the office, if you need something more substantial. The mattress and pillows were so comfortable that I had trouble getting myself up the next morning! Slept like a rock. 10/10 for the Windmill! Can't wait to see what the restaurant will be like when it opens! I will definitely come back next year, if there is availability!"
June 1-night trip
Posted 2 days ago
Windmill Motel Restaurant
Latchis Hotel

Latchis Hotel

8/10 Good
"In an old Theater building. Definitely has character and cool features. We arrived too late for the movies, but still fun. In central Brattleboro which has some interesting shops, but is suffering from homelessnes and mental illness/drug use. Didnt really feel unsafe and we walked a few blocks to a fun restaurant with good food & karioke. Person at desk was lovely and helpful. Room was ok- a little dated and could be cleaner."
Jonathan 1-night trip
Posted 2 days ago
Latchis Hotel
The Putney Inn

The Putney Inn

8/10 Good
"I feel the 8.6 is much too overrated. A 7, maybe. Old building, needs a facelift. Clean, but does not feel as a happy place. Old rugs. Very dark ( but clean) rooms. Felt like in a cave. Manager had no people skills, not welcoming. Will not stay there again. Put a little money into the place!"
irina 1-night trip
Posted 3 days ago
The Putney Inn

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