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

Hotels with Restaurants in Windham County from $84

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Top Cities in Windham County

A calm lake reflecting a forest with autumn foliage.
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Brattleboro

Brattleboro

Check availability on Windham County Hotels with Restaurants

Our top choices for Windham County hotels with a restaurant

Restaurant

The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
2.5 star property
Londonderry
8.2 out of 10, Very Good, (701 reviews)
"Charming rustic inn. Staff were delightful and food was great. "
United States
Bradley
$107 nightly
The price is $118
Aug 17 - Aug 18
Total with taxes and fees
The Upper Pass Lodge at Magic Mountain
Lobby

Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
5.8 out of 10, (22 reviews)
"Clean room ez checkin, coffee at breakfast good!"
United States
James
$77 nightly
The price is $84
Aug 2 - Aug 3
Total with taxes and fees
Colonial Motel
Outdoor wedding area

The Nutmeg

The Nutmeg
3.5 star property
Wilmington
9.4 out of 10, Exceptional, (435 reviews)
"Lovely B&B, and the staff were fantastic. Breakfast was delicious each morning. Common areas were charming."
United States
Melinda
$180 nightly
The price is $198
Aug 17 - Aug 18
Total with taxes and fees
The Nutmeg
Exterior

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,003 reviews)
"Perfect for an overnight!"
United States
Lori
$137 nightly
The price is $150
Aug 7 - Aug 8
Total with taxes and fees
The Putney Inn
Porch

The Wilmington Inn

The Wilmington Inn
3.5 star property
Wilmington
10.0 out of 10, Exceptional, (205 reviews)
"Staff was wonderful, breakfast great and room was clean"
United States
Mary Beth
$241 nightly
The price is $265
Jul 23 - Jul 24
Total with taxes and fees
The Wilmington Inn
WiFi (free), bed sheets

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (1,002 reviews)
"The beds were very squeaky. Pillows too big"
United States
Patti
$134 nightly
The price is $148
Aug 10 - Aug 11
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (933 reviews)
"This hotel was the perfect landing place from a lot of traveling. It was clean, had unique historic ambience, and walkable to the whole town. Highly recommend!"
United States
Laurel
$128 nightly
The price is $140
Jul 20 - Jul 21
Total with taxes and fees
Latchis Hotel
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (835 reviews)
"Staff wasfriendly and my room is very clean"
United States
Michael
$123 nightly
The price is $136
Aug 16 - Aug 17
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (1,001 reviews)
"Really great spot for the price, very happy with our short stay."
United States
Kyle
$121 nightly
The price is $134
Aug 12 - Aug 13
Total with taxes and fees
Hampton Inn Brattleboro
Lobby

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,001 reviews)
"The staff was able to recommend places to go and eat, which was really nice."
United States
Alyssa
$126 nightly
The price is $139
Jul 26 - Jul 27
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windham County Hotel Reviews

Inn At Mount Snow

Inn At Mount Snow

10/10 Excellent
"Enjoyed the private balcony. Property manager, Chance, was extremely helpful and friendly, during both check-in and during our stay. The room was very clean and property amenities made our stay enjoyable. I would definitely stay here again if I ever pass through southern Vermont again."
Robert 2-night trip
Posted 6 hours ago
Inn At Mount Snow

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Frequently asked questions

How much do hotels with dining in Windham County cost?
Hotels in Windham County range between $84 to $265 per night. Come with an appetite — these hotels have restaurants or are near top dining experiences. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with dining in Windham County?
Get ready to experience the culinary delights of Windham County when you stay at one of our multiple hotels with restaurants or close to foodie areas. With a total average guest review rating of 8.5, there's an irresistible option for every taste and budget. If you're headed to Wilmington, check out Kitzhof Inn, a 2.5-star getaway with a garden and a barbecue grill. Another traveler favorite in Wilmington is The White House Inn. This 3.5-star stay offers a terrace and a garden.
How many hotels with dining are there in Windham County?
Windham County has 47 hotels with access to some appetizing food experiences. Enter your travel dates and destination and book your perfect trip today.
Why book your hotel with dining in Windham County with Expedia?
With Expedia, you'll have no trouble finding your dream hotel with dining in Windham County. Make use of our filters to search for properties with an on-site restaurant. If you're sticking to a budget, click on how much you'd like to spend and the star rating of your hotel. We'll help you find the perfect stay whatever your tastes or bank balance.
How can I find cheap hotels with dining in Windham County?
The easiest way to get cheap hotels with dining in Windham County is with Expedia's convenient filter tool. Book getaways with restaurants or a few extras, like included breakfast. You can also fine-tune your search results by budget, star rating and amenities to access awesome rates in just a few keystrokes.
What is there to do in Windham County near my hotel with dining?
Whether you're heading north, south, east or west in Windham County, you'll find tons of fun things to keep you busy. Planning to stay in Stratton? Stratton Golf School is one attraction to put on your itinerary.