Windham Guest Houses

A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

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Our top choices for Windham guest houses

A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.

1. Shadowcrest

Fleischmanns

Margo

includes taxes & fees

27 Sept - 28 Sept

A modern house with a wooden deck, a fire pit, and a covered outdoor seating area.

2. The Herwood Inn

Woodstock

John

includes taxes & fees

30 Sept - 1 Oct

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Top Windham Hotel Reviews

Jimmy OConnors Windham Mountain Inn

10/10 Excellent

"Cool little spot with the inn at the back of the property and the restaurant at the front. It’s been passed down through the family and I met the owner inside during a quick dinner, down to earth guy. The room is very vey clean and still sporting the original textures and fixtures, real retro feeling, I loved it."

Emerson Resort & Spa

10/10 Excellent

"If you are looking for a very peaceful, serene getaway to completely reset, book this place immediately. The quiet, beautiful atmosphere makes it a true sanctuary.The hospitality here is next level. Jackie was incredibly nice and welcoming from start to finish. Jonathan went out of his way to take gorgeous birthday pictures for me the second I asked. The absolute hero of my trip was Kristine, who literally saved me when I found myself stranded in the middle of nowhere!This team protects your peace of mind, I am telling everyone about this gem, and I am definitely coming back to the Emerson!"

The Winwood Condominiums

10/10 Excellent

"I came here thirty years ago. And I came here thirty years later, and it's still run by a wonderful proprietor and it's a beautiful place to unwind, and enjoy breakfast in the morning will be a wonderful host if she's not busy. That is taking care of this amazing place. I very much enjoyed my stay"

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