Windham County Winery Hotels from AED 705

A wooden covered bridge over a river with stone walls on either side.

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Our top choices for Windham County hotels with winery

An outdoor deck with a wooden table and wicker chairs, surrounded by a wooden railing and string lights.

1. The Wilmington Inn

Wilmington

Jay

AED 870 total

includes taxes & fees

8 Nov - 9 Nov

A glass table with a vase of white lilies, a glass dome containing cookies, and a blue chair in a room with white walls and a window.

2. The Nutmeg

Wilmington

Susan

AED 705 total

includes taxes & fees

7 Dec - 8 Dec

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Top Windham County Hotel Reviews

Hampton Inn Brattleboro

10/10 Excellent

"Great stay in a newly renovated room. Clean and comfortable. I have stayed before the renovation and will happily stay again."

Otherland Hotel

10/10 Excellent

"We had such a great stay at The Otherland Hotel and would absolutely give it a 10/10. Everything felt updated, modern, and very clean. The common areas were especially nice — comfortable and inviting, with a fireplace upstairs and a small kitchenette downstairs with a microwave, sink, and water dispenser, which was really convenient for warming up food. The bed and pillows were incredibly comfortable, and we loved being able to sit outside by the fire pit for a while. It was also perfect for traveling with our dog because she had plenty of room to run around in the fields. There are lots of thoughtful little touches throughout the hotel too, including board games and books in the common rooms for guests to enjoy. It felt cozy, relaxed, and very well cared for. We would definitely stay here again."

Hideaway Inn Mt. Snow

10/10 Excellent

"The room was small and simple, but nicely decorated, including a record player with a vinyl album (cover, at least; didn't check for actual vinyl). The room was warm and the place was quiet when I stayed, which was off-season. I've been pulling into the parking lot of this place for five years now (MOOver), so staying there was interesting for me. I stayed there during a HAZMAT spill that closed Woodford Mtn for a couple days. Of special note, this is the ONLY hotel I've ever stayed at that had a sleep/sound machine in the room. I ALWAYS take one with me when traveling, but this was a last minute decision, so I would've had to pull up something on my phone, but there was a nice sound machine on the nightstand and I used it. Those are so helpful when staying in hotels/inns."

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent

"A one-night stay. It had everything we needed. Not fancy, but it was all there, clean and bright. It is right next to the Interstate, but we could not hear any road traffic, so for the win. The morning breakfast scene is complete. The staff was very polite and accommodating."

Room 1

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Treat yourself

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Check availability on Windham County Winery Hotels

Our top choices for Windham County hotels with winery

1. The Wilmington Inn

2. The Nutmeg

Top Windham County Hotel Reviews

Hampton Inn Brattleboro

Travelodge by Wyndham Brattleboro VT

Comfort Inn & Suites Brattleboro I-91

Otherland Hotel

Hideaway Inn Mt. Snow

The Putney Inn

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Grand Summit Resort, A Vail Resorts Property

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Winery Hotels in Windham County from AED 705

Change your mind

Treat yourself

Be picky

Check availability on Windham County Winery Hotels

Our top choices for Windham County hotels with winery

1. The Wilmington Inn

2. The Nutmeg

Top Windham County Hotel Reviews

Hampton Inn Brattleboro

Explore a world of travel with Expedia