Winchester Holiday Homes from £153: Search Holiday Homes in Winchester

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Our top choices for Winchester holiday homes

Lovely 2nd Floor Apartment

Greenfield

Emily Kate G.

includes taxes & fees

8 Jun - 9 Jun

Stunning Glass House nestled in the Vermont wilderness!

Guilford

"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."

Grant D.

includes taxes & fees

8 Jun - 9 Jun

Private bed with En-suite bathroom Marigold Room

Shelburne Falls

includes taxes & fees

8 Jun - 9 Jun

John's Mountain Hideaway

Jaffrey

includes taxes & fees

7 Jun - 8 Jun

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Keene

Jeremy S.

includes taxes & fees

8 Jun - 9 Jun

Family Friendly Hilltop House In Putney Vermont

Putney

Susan O.

includes taxes & fees

10 Jun - 11 Jun

Enjoy your stay in an antique home in an antique toy museum!

Winchendon

Katja Z.

includes taxes & fees

7 Jun - 8 Jun

Spacious 5BR w/ Hot Tub & Games

Colrain

Maureen A.

includes taxes & fees

8 Jun - 9 Jun

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Top Winchester Hotel Reviews

Latchis Hotel

8/10 Good

"The historic hotel was interesting to sty in. The theater as part of it, was great. I would have preferred tobe able to control the room temperature. One negative was the bleach used on the sheets. I had an allergic reaction to it that cause my eyes to be red and painful. Perhaps hotel can use another color."

Econo Lodge Brattleboro South

2/10 Terrible

"We picked this motel because it was next to the bus stop otherwise if we knew better, wouldn't have stayed here. Nobody at the front desk so had to call someone to book us in. Our room was run down, floors and counter were sticky and when we opened the fridge, there was food left from the previous guest so that just proves it wasn't cleaned properly. Broken window shades, no cups, soap etc in the room. No laundry facilities on site and no ice machine and breakfast available anymore. They wouldn't let us move to another room even though there was a lot available. We paid ahead of time so no refund was allowed. Way too much for your money.Bewarned"