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Top Cities in Windham County

We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!
HotelsHotels

Brattleboro

Brattleboro

Check prices for these dates

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Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

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Our top choices for Windham County hotels

Exterior
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property
3.0 star property
West Dover
8.8 out of 10, Excellent, (244)
"Great place to stay!"
United States
Sonia
The price is ￥48,303
￥57,809 total
includes taxes & fees
Dec 23 - Dec 24
Grand Summit Resort, A Vail Resorts Property
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, (944)
"Place definitely needs some updating but it was clean and the staff was great!"
United States
Jacqueline
The price is ￥27,725
￥33,546 total
includes taxes & fees
Jan 19 - Jan 20, 2026
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, (1002)
"Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street. "
United States
Megan
The price is ￥14,197
￥15,615 total
includes taxes & fees
Dec 23 - Dec 24
The Covered Bridge Inn
Fireplace
Mountaineer Inn

Mountaineer Inn

Mountaineer Inn
2.0 star property
West Dover
8.6 out of 10, Excellent, (551)
"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
Double Room | Terrace/patio
Chalet 239

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (93)
"Great clean place. "
United States
Les
The price is ￥30,563
￥33,618 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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
The price is ￥28,119
￥30,930 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Big Bears Lodge
Restaurant
The White House Inn

The White House Inn

The White House Inn
3.5 star property
Wilmington
9.2 out of 10, Wonderful, (265)
"We stayed at the White House in two weekends in a row while our house was under construction. We loved that they had music until 9 and that the room was clean and the beds were comfortable. The staff made sure we had everything we needed. We would definitely recommend."
United States
Stacy
The price is ￥26,123
￥28,735 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The White House Inn
Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (928)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is ￥23,155
￥25,471 total
includes taxes & fees
Dec 30 - Dec 31
Hampton Inn Brattleboro
Property amenity
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (3)
"Really happy with our stay and the way we felt at this hideaway "
United States
Edwin
The price is ￥17,519
￥19,271 total
includes taxes & fees
Dec 23 - Dec 24
Hideaway Inn Mt. Snow
Porch
Valley Craft Ales

Valley Craft Ales

Valley Craft Ales
2.0 star property
Wilmington
8.4 out of 10, Very Good, (188)
"The staff and amenities were fantastic"
United States
Matthew
Valley Craft Ales
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
The price is ￥60,695
￥75,444 total
includes taxes & fees
Jan 12 - Jan 13, 2026
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, (53)
"Great location for an overnight stay to hit the slopes. Will definitely visit again. "
United States
Ryan
The price is ￥36,724
￥40,396 total
includes taxes & fees
Jan 13 - Jan 14, 2026
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
The price is ￥45,708
￥56,815 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Vantage Point Villas at Stratton Mountain Resort
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1003)
"Nice motel. "
United States
Richard
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, (737)
"Bitten up motel needs renovation definitely. "
United States
Piotr
The price is ￥8,377
￥9,214 total
includes taxes & fees
Dec 25 - Dec 26
Travelodge by Wyndham Brattleboro VT
Seasonal outdoor pool
Econo Lodge Brattleboro

Econo Lodge Brattleboro

Econo Lodge Brattleboro
2.0 star property
Brattleboro
5.4 out of 10, (605)
"Room was dirty, tv was tiny..very poor value"
United States
Raymond
The price is ￥8,177
￥8,995 total
includes taxes & fees
Dec 28 - Dec 29
Econo Lodge Brattleboro
Exterior
Colonial Motel And Spa

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1004)
"Nice place to stay for the night."
United States
Robin
The price is ￥18,141
￥19,955 total
includes taxes & fees
Dec 23 - Dec 24
Colonial Motel And Spa
Exterior
Latchis Hotel

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very Good, (837)
"Great stay"
United States
Jason
The price is ￥17,571
￥19,329 total
includes taxes & fees
Dec 26 - Dec 27
Latchis Hotel
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (88)
"We had a lovely time staying here. "
United States
Jeff
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, (741)
"Price, clean and spacious room, comfy bed."
United States
June
The price is ￥18,769
￥20,645 total
includes taxes & fees
Dec 28 - Dec 29
Comfort Inn & Suites Brattleboro I-91
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:Jan 2 - Jan 4

Image gallery for Chalet 239

Double Room | Terrace/patio

Chalet 239

2.0 star property
West Dover
9.4/10Exceptional (93 reviews)
10% off
Price is ￥42,450
￥93,392 total
includes taxes & fees
Chalet 239
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Top Windham County Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"Very quit, clea, and comfortable. "
Jeannette 1-night trip
Posted 3 days ago
The Putney Inn

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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 ￥8,995 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 12ºC to 24ºC. 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 ￥8,995 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?
We make booking a stay in Windham County as simple as swiping right for your dream escape. First, there's the broad range of options and awesome prices. Then, there's our online Help Center, which is available 24/7. Plus, when you join our free One Key™ loyalty program, you can earn OneKeyCash™* and redeem it on eligible flights, hotels, car rentals and more.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.