Photo by Donny Campos

Search Hotels in Windham County

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Windham County hotels

Front of property
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 AEDĀ 1,133
AEDĀ 1,356 total
includes taxes & fees
13 Jan - 14 January 2026
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 AEDĀ 618
AEDĀ 748 total
includes taxes & fees
19 Jan - 20 January 2026
The Black Bear Lodge at Stratton Mountain Resort
Exterior detail
The Covered Bridge Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
"Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street. "
United States
Megan
The price is AEDĀ 286
AEDĀ 315 total
includes taxes & fees
28 Dec - 29 Dec
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 weā€™d stay again "
United States
Joseph
Mountaineer Inn
Family Room | Living area | Smart TV
Chalet 239

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (95)
"Great clean place. "
United States
Les
The price is AEDĀ 681
AEDĀ 749 total
includes taxes & fees
26 Jan - 27 January 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 AEDĀ 655
AEDĀ 720 total
includes taxes & fees
1 Jan - 2 January 2026
Big Bears Lodge
Interior detail
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 AEDĀ 608
AEDĀ 669 total
includes taxes & fees
4 Jan - 5 January 2026
The White House Inn
Free breakfast
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 AEDĀ 539
AEDĀ 593 total
includes taxes & fees
2 Jan - 3 January 2026
Hampton Inn Brattleboro
Interior
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (4)
"Really happy with our stay and the way we felt at this hideaway "
United States
Edwin
The price is AEDĀ 484
AEDĀ 532 total
includes taxes & fees
4 Jan - 5 January 2026
Hideaway Inn Mt. Snow
Interior detail
Valley Craft Ales

Valley Craft Ales

Valley Craft Ales
2.0 star property
Wilmington
8.4 out of 10, Very Good, (190)
"The staff and amenities were fantastic"
United States
Matthew
Valley Craft Ales
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
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
8.4 out of 10, Very Good, (78)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is AEDĀ 1,383
AEDĀ 1,720 total
includes taxes & fees
5 Jan - 6 January 2026
Long Trail House at Stratton Mountain Resort
Exterior
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 AEDĀ 811
AEDĀ 892 total
includes taxes & fees
4 Jan - 5 January 2026
Inn At Mount Snow
Outdoor 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 AEDĀ 997
AEDĀ 1,239 total
includes taxes & fees
26 Jan - 27 January 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, (1001)
"The room was okay for a quick stop to rest. "
United States
Janice
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 AEDĀ 195
AEDĀ 215 total
includes taxes & fees
28 Dec - 29 Dec
Travelodge by Wyndham Brattleboro VT
View from room
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 AEDĀ 241
AEDĀ 265 total
includes taxes & fees
28 Dec - 29 Dec
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, (1001)
"Nice place to stay for the night."
United States
Robin
The price is AEDĀ 441
AEDĀ 485 total
includes taxes & fees
28 Dec - 29 Dec
Colonial Motel And Spa
Hiking
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 AEDĀ 476
AEDĀ 524 total
includes taxes & fees
28 Dec - 29 Dec
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, (743)
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
United States
Jack
The price is AEDĀ 435
AEDĀ 478 total
includes taxes & fees
28 Dec - 29 Dec
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.
View all properties

Great weekend hotel deals inĀ Windham County, VT

Showing deals for:2 Jan - 4 Jan

Image gallery for Hideaway Inn Mt. Snow

Interior

Hideaway Inn Mt. Snow

2.0 star property
West Dover
10/10Exceptional (4 reviews)
Member Price available
Price is AEDĀ 951
AEDĀ 2,091 total
includes taxes & fees
Sign in for Member Price
Hideaway Inn Mt. Snow
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham County Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"Staff was courteous "
Jessyca 1-night trip
Posted 2 days ago
The Putney Inn

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 AEDĀ 215 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 12ĀŗC to 24ĀŗC. 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 AEDĀ 215 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?
Expedia is your one-stop shop for organising the ultimate holiday experience in Windham County. You'll find a wide variety of hotels to choose from and search filters that make it a breeze to find the stay of your dreams. Worried about your plans changing? Many of our hotels have flexible cancellation policies, so you can book with peace of mind. Get more out of your trip with Expedia Rewards. Join today for free and you can collect points and unlock membership perks. You'll enjoy instant access to Member Prices, which adds up to savings worth 10% or more on select hotels!