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

Hotels with Restaurants in Windham County from $88

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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

This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Windham County hotels with a restaurant

A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.

1. 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, (704 reviews)
"Very nice staff easy access to everything good for dogs clean pool"
United States
Terry
$80 nightly
The price is $88
Sep 28 - Sep 29
Total with taxes and fees
The Upper Pass Lodge at Magic Mountain
A cozy living room with a fireplace, a coffee station, and a view of the outside.

2. Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.8 out of 10, (46 reviews)
"Clean room ez checkin, coffee at breakfast good!"
United States
James
$83 nightly
The price is $91
Sep 6 - Sep 7
Total with taxes and fees
Colonial Motel
A stone fire pit surrounded by a grassy area with a tree and outdoor seating.

3. The Nutmeg

The Nutmeg
3.5 star property
Wilmington
9.4 out of 10, Exceptional, (440 reviews)
"Location and Friendly staff"
United States
David
$177 nightly
The price is $194
Sep 10 - Sep 11
Total with taxes and fees
The Nutmeg
A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

4. The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,001 reviews)
"Clean room, staff, breakfast, and parking were great!"
United States
JANE
$121 nightly
The price is $133
Aug 31 - Sep 1
Total with taxes and fees
The Putney Inn
An outdoor deck with a wooden table and wicker chairs, surrounded by a wooden railing and string lights.

5. The Wilmington Inn

The Wilmington Inn
3.5 star property
Wilmington
10.0 out of 10, Exceptional, (206 reviews)
"Staff was wonderful, breakfast great and room was clean"
United States
Mary Beth
$256 nightly
The price is $282
Aug 29 - Aug 30
Total with taxes and fees
The Wilmington Inn
A hotel room with two beds, a window with blinds, a desk with a television, and a lamp.

6. 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, (1,000 reviews)
"It was very expensive for off-season"
United States
Roberta
$131 nightly
The price is $144
Aug 31 - Sep 1
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
The exterior of Latchis Hotel with a prominent entrance, large windows, and potted plants.

7. Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (967 reviews)
"Excellent location"
United States
Stark
$160 nightly
The price is $175
Aug 30 - Aug 31
Total with taxes and fees
Latchis Hotel
A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

8. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (849 reviews)
"The front desk staff were friendly and engaged, the room was clean. That’s all we needed."
United States
Morgan
$118 nightly
The price is $130
Sep 6 - Sep 7
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.

9. Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (1,001 reviews)
"Great breakfasts!"
United States
Timothy
$112 nightly
The price is $123
Sep 8 - Sep 9
Total with taxes and fees
Hampton Inn Brattleboro
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.

10. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1,013 reviews)
"One of our favorite hotels in Brattleboro. Clean, safe and the staff are super friendly."
United States
Marnie
$169 nightly
The price is $186
Sep 13 - Sep 14
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

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"my fav. vacation place!!!"
Melissa 1-night trip
Posted 16 hours ago
Vikings Villages Resort

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Frequently asked questions

How much do hotels with dining in Windham County cost?
Hotels in Windham County range between $88 to $282 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 8.3, 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.