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Search Hotels in Windham County

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Top Cities in Windham County

Stratton Pond #oxfordthemini
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Stratton

Stratton

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Dec 13 - Dec 14
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Dec 14 - Dec 15
Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28

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Our top choices for Windham County hotels

Exterior
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort
3.0 star property
West Dover
8.8 out of 10, Excellent, (243)
"Great place to stay!"
United States
Sonia
$243 nightly
The price is $268
Dec 15 - Dec 16
Total with taxes and fees
Mount Snow Grand Summit Resort
Free WiFi, bed sheets
The Black Bear Lodge at Stratton Mountain Resort

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, (940)
"We like that getting to Stratton Mountain and the downtown area was very walkable or easy to get there by regularly running shuttle buses."
United States
Mark
$185 nightly
The price is $204
Jan 7 - Jan 8, 2026
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
Breakfast area
The Covered Bridge Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
$70 nightly
The price is $77
Dec 28 - Dec 29
Total with taxes and fees
The Covered Bridge Inn
Fireplace
Mountaineer Inn

Mountaineer Inn

Mountaineer Inn
2.0 star property
West Dover
8.6 out of 10, Excellent, (550)
"Small but clean room. Hotel is under construction but staff was accommodating and pleasant to work with durning our travel. If traveling for work we’d stay again "
United States
Joseph
Mountaineer Inn
Seasonal outdoor pool
Econo Lodge Brattleboro

Econo Lodge Brattleboro

Econo Lodge Brattleboro
2.0 star property
Brattleboro
5.4 out of 10, (601)
"Room was dirty, tv was tiny..very poor value"
United States
Raymond
$52 nightly
The price is $57
Dec 21 - Dec 22
Total with taxes and fees
Econo Lodge Brattleboro
Double Room | Terrace/patio
Chalet 239

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (89)
"Great place for a quick trip to VT!"
United States
Rory
$149 nightly
The price is $164
Dec 15 - Dec 16
Total with taxes and fees
Chalet 239
Garden
Big Bears Lodge

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
$167 nightly
The price is $183
Dec 14 - Dec 15
Total with taxes and fees
Big Bears Lodge
Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (925)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
$143 nightly
The price is $158
Dec 19 - Dec 20
Total with taxes and fees
Hampton Inn Brattleboro
Restaurant
The White House Inn

The White House Inn

The White House Inn
3.5 star property
Wilmington
9.2 out of 10, Wonderful, (262)
"The room was beautiful and the historic charm was wonderful "
United States
Karin
$184 nightly
The price is $202
Jan 4 - Jan 5, 2026
Total with taxes and fees
The White House Inn
Porch
Valley Craft Ales

Valley Craft Ales

Valley Craft Ales
2.0 star property
Wilmington
8.4 out of 10, Very Good, (184)
"Fun place to stay!!"
United States
Brian
$94 nightly
The price is $104
Dec 17 - Dec 18
Total with taxes and fees
Valley Craft Ales
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1002)
"Nice motel. "
United States
Richard
$78 nightly
The price is $86
Dec 25 - Dec 26
Total with taxes and fees
The Putney Inn
Reception
Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (736)
"Reasonable rate for the the accomadations."
United States
David
$71 nightly
The price is $78
Dec 16 - Dec 17
Total with taxes and fees
Travelodge by Wyndham Brattleboro VT
Exterior
Latchis Hotel

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very Good, (836)
"Great stay"
United States
Jason
$119 nightly
The price is $131
Dec 16 - Dec 17
Total with taxes and fees
Latchis Hotel
Exterior
Colonial Motel And Spa

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1002)
"Nice place to stay for the night."
United States
Robin
$104 nightly
The price is $114
Dec 21 - Dec 22
Total with taxes and fees
Colonial Motel And Spa
Outdoor spa tub
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
$415 nightly
The price is $469
Jan 13 - Jan 14, 2026
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
Lobby sitting area
Inn At Mount Snow

Inn At Mount Snow

Inn At Mount Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (52)
"From start to finish the staff could not do enough for you and the quality of the inn was amazing"
United Kingdom
Andrew
$120 nightly
The price is $132
Dec 16 - Dec 17
Total with taxes and fees
Inn At Mount Snow
Family dining
Vantage Point Villas at Stratton Mountain Resort

Vantage Point Villas at Stratton Mountain Resort

Vantage Point Villas at Stratton Mountain Resort
3.0 star property
Stratton
8.4 out of 10, Very Good, (70)
"Amazing stay - The condo was cozy and perfect for our family! "
United States
Kate
$306 nightly
The price is $346
Dec 18 - Dec 19
Total with taxes and fees
Vantage Point Villas at Stratton Mountain Resort
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (86)
"We had a lovely time staying here. "
United States
Jeff
$175 nightly
The price is $193
Dec 14 - Dec 15
Total with taxes and fees
Deerfield Valley Inn
Lobby
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (740)
"Price, clean and spacious room, comfy bed."
United States
June
$107 nightly
The price is $118
Dec 21 - Dec 22
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
Restaurant
The Upper Pass Lodge at Magic Mountain

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, (687)
"This place was a dream, everybody was so nice! We felt at home and safe."
United States
Gracie
$126 nightly
The price is $138
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Upper Pass Lodge at Magic Mountain
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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Great weekend hotel deals in Windham County, VT

Showing deals for:Dec 26 - Dec 28

Image gallery for Brook Bound Inn

Family Cabin | Living area | 30-inch LCD TV with cable channels

Brook Bound Inn

2.0 star property
Wilmington
9.6/10Exceptional (11 reviews)
16% off
$296 nightly
Price is $652
Total with taxes and fees
Brook Bound Inn
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Top Windham County Hotel Reviews

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Complimentary breakfast was nice. Room was clean. "
Scott 1-night trip
Posted 5 days ago
The Black Bear Lodge at Stratton Mountain Resort

Price trends for hotels in Windham County

Less expensive
More expensive
This month
Next month
November
January
$168
$180
Month
Price
January
$180
February
$176
March
$164
April
$161
May
$160
June
$167
July
$170
August
$173
September
$165
October
$173
November
$149
December
$168
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Windham County. Select dates and complete search for nightly totals inclusive of taxes and fees.

Explore a world of travel with Expedia

Frequently asked questions

How much do hotels in Windham County cost?
The season and factors like Easter and school holidays can influence the price of a hotel in Windham County. You can find cheap options from $57 in a few different ways on Expedia. First, select the dates you'd like to get away, then use the filters like property type and amenities to fine-tune your search. You can also sort by price, so the lowest options appear at the top.
When is the best time to go to Windham County?
If you want to visit in summer, reserve your Windham County hotel between June and August. Temperatures during the summer months here range from 54ºF to 75ºF. Windham County has a humid continental climate, so pack accordingly.
How can I find cheap hotels in Windham County?
Windham County cheap hotels start at $57 per night. To browse these types of wallet-friendly options, make use of our "Price per night" filter. Like some other tips? Be flexible with your vacation dates and book early. Check out our cheap hotels in Windham County page for deals you won't be able to resist.
What are the best hotels in Windham County for families?
Big Bears Lodge is among the most popular hotels for families, located in Stratton, Windham County. Stay here and take advantage of amenities like a playground and complimentary breakfast. Three Mountain Inn is another favorite property where kiddos are welcome. For more hotel options, fine-tune your search results by clicking on "Family friendly" under the "Traveler experience" filter section.
Why should I book my Windham County hotel with Expedia?
Book your Windham County hotel with Expedia for price, ease and choice. Also, our One Key™ rewards program lets you collect OneKeyCash™* on eligible flights, car rentals, activities, hotels and more. Plus, we offer flexibility should your schedule change, and if you want to ask us anything or require assistance, our online Help Center is always available. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.