Best Resorts in Windham County

Compare and save

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Feb 27 - Mar 1
In two weeks
Mar 6 - Mar 8
In one month
Mar 20 - Mar 22
In two months
Apr 17 - Apr 19

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!
ResortsResorts

Brattleboro

Brattleboro

Our top choices for Windham County resorts

Exterior

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, (256 reviews)
"Ski slopes were accessible and pool was really nice. "
United States
Claudia
$343 nightly
The price is $377
Mar 9 - Mar 10
Total with taxes and fees
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
3.0 star property
Stratton
7.6 out of 10, Good, (972 reviews)
"Very friendly staff, excellent location. Breakfast was great and room was just what we needed"
United States
Val
$190 nightly
The price is $209
Mar 1 - Mar 2
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
1 bedroom, iron/ironing board, WiFi

Deluxe 2xQueen- 2nd floor in Historic Inn

Deluxe 2xQueen- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"Everything was just fantastic! Everyone was friendly and accommodating. Owners were so nice! Property is amazing and a great location to Mount Snow. Can not go wrong with this spot."
United States
Brendan M.
$278 nightly
The price is $302
Feb 23 - Feb 24
Total with taxes and fees
Deluxe 2xQueen- 2nd floor in Historic Inn
Interior

Luxury King with balcony

Luxury King with balcony
West Dover
$279 nightly
The price is $303
Feb 22 - Feb 23
Total with taxes and fees
Luxury King with balcony
Exterior

King with Bunk Bed- 2nd floor in Historic Inn

King with Bunk Bed- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Very well apportioned room. Super clean and comfortable. Restaurant was delicious. Bartender is cool to chat with."
United States
Forrest W.
$279 nightly
The price is $303
Feb 22 - Feb 23
Total with taxes and fees
King with Bunk Bed- 2nd floor in Historic Inn
Exterior

Deluxe King, kitchenette, fireplace

Deluxe King, kitchenette, fireplace
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"End of season special. Perfect size, fireplace was great on a cold rainy night. Last night restaurant was open for a few weeks."
United States
john L.
$315 nightly
The price is $342
Feb 25 - Feb 26
Total with taxes and fees
Deluxe King, kitchenette, fireplace
Exterior

Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
$279 nightly
The price is $303
Feb 22 - Feb 23
Total with taxes and fees
Deluxe King - 2nd floor in Historic Inn
Interior

Deluxe King Room w/fireplace and separate entrance

Deluxe King Room w/fireplace and separate entrance
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our one-night stay. Our room was cozy and all the staff were wonderful."
United States
Charles B.
$319 nightly
The price is $347
Feb 22 - Feb 23
Total with taxes and fees
Deluxe King Room w/fireplace and separate entrance
Dining

Deluxe King Room w/pull-out love seat and fireplace

Deluxe King Room w/pull-out love seat and fireplace
Dover
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfect"
United States
James R.
$315 nightly
The price is $342
Feb 22 - Feb 23
Total with taxes and fees
Deluxe King Room w/pull-out love seat and fireplace
Interior

Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance

Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Dover
9.8 out of 10, Exceptional, (7 reviews)
"My husband and I stayed here so we could ride Mt Snow for a few days. The place is wonderful! All staff is incredibly helpful and friendly, the food and cocktails in their restaurant are phenomenal, the landscape and accommodation are beautiful. We will definitely be back."
United States
Sydney W.
$370 nightly
The price is $403
Feb 23 - Feb 24
Total with taxes and fees
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
1 bedroom, iron/ironing board, WiFi

Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths

Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
West Dover
8.0 out of 10, Very Good, (1 review)
"The inn and grounds were wonderful. Great food at the Sawmill. Wonderful area to explore leading to an all around wonderful time."
United States
Craig C.
$293 nightly
The price is $318
Feb 25 - Feb 26
Total with taxes and fees
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
Exterior

Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
Dover
9.4 out of 10, Exceptional, (6 reviews)
"This is a beautiful, large suite in a quaint Vermont town. There are two main rooms: a bedroom with a king bed and a bunk bed, and a separate living room with a fireplace. The main inn also has lounge areas open to guests all night, and is a perfect stay for both families and couples. "
United States
Olivia
$389 nightly
The price is $424
Mar 24 - Mar 25
Total with taxes and fees
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
Interior

Deluxe Queen Suite with pull-out love seat, private entrance

Deluxe Queen Suite with pull-out love seat, private entrance
Dover
$350 nightly
The price is $382
Mar 24 - Mar 25
Total with taxes and fees
Deluxe Queen Suite with pull-out love seat, private entrance
Exterior

Deluxe King- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn
West Dover
$253 nightly
The price is $275
Feb 22 - Feb 23
Total with taxes and fees
Deluxe King- 2nd floor in Historic Inn
Exterior

Luxury King Suite, Living Room w/sofa bed and jacuzzi tub

Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Such a quaint, beautiful Spot. It’s uniqueness, historic feel and common area was very warming. Personnel was very friendly and attentive"
United States
Jessica
$291 nightly
The price is $316
Feb 23 - Feb 24
Total with taxes and fees
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
Exterior

Deluxe King, Living Room w/sofa bed & fireplace

Deluxe King, Living Room w/sofa bed & fireplace
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Had a really nice time - the place was lovely. They had some on property activities and were very close to the mountain. We had a great time and would definitely stay here again if back in the area!"
United States
Taylor G.
$318 nightly
The price is $346
Feb 23 - Feb 24
Total with taxes and fees
Deluxe King, Living Room w/sofa bed & fireplace
Exterior

Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
$267 nightly
The price is $290
Feb 22 - Feb 23
Total with taxes and fees
Deluxe King - 2nd floor in Historic Inn
Exterior

Luxury King w/balcony, accessible

Luxury King w/balcony, accessible
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"My husband and I had a wonderful time at the Inn . our room was beautiful and we had two delicious meals in the restaurant I would definitely recommend this Inn to anyone traveling in southern Vermont."
United States
Kimberley B.
$279 nightly
The price is $303
Feb 22 - Feb 23
Total with taxes and fees
Luxury King w/balcony, accessible
1 bedroom, iron/ironing board, WiFi

Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance

Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
Dover
10.0 out of 10, Exceptional, (2 reviews)
"The place was clean, cozy and comfortable. The whole estate is beautiful."
United States
Mike T.
$389 nightly
The price is $424
Mar 24 - Mar 25
Total with taxes and fees
Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
Exterior

Deluxe King Suite, Living Room w/sofa bed & fireplace

Deluxe King Suite, Living Room w/sofa bed & fireplace
West Dover
10.0 out of 10, Exceptional, (1 review)
"My husband and I really enjoyed the accommodations. Great location with tons do do nearby. The place was so cozy and inviting. Would definitely stay again"
United States
Megan M.
$315 nightly
The price is $342
Feb 24 - Feb 25
Total with taxes and fees
Deluxe King Suite, Living Room w/sofa bed & fireplace
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

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
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
"Great staff"
Kyle 1-night trip
Posted 5 days ago
The Putney Inn

Find out more about Windham County

Windham County Resorts information

Number of reviews
1,014
Accommodation
26 Resorts
Lowest Price
$209
Highest Price
$424

Frequently asked questions

How much do resorts in Windham County cost?
Rates for resorts in Windham County range between $209 and $424 per night. Whether you're seeking an affordable family resort or an upscale couples-only retreat, you're sure to land the ideal stay with Expedia. This price was 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 resorts in Windham County?
Jump right into vacation mode and get some well-deserved R&R in one of Windham County's multiple resorts. With a total average guest review rating of 9.6, there's something here for every budget and taste. Many visitors to Stratton recommend a stay at Mount Snow Grand Summit Resort, a 3-star option with a cafe and a spa. Another unbeatable choice in this popular city is The Black Bear Lodge at Stratton Mountain Resort. This 3-star escape offers mountain views and many nearby bars.
How many resorts are there in Windham County?
Browse through 26 resorts in Windham County and lock in your favorite. Whether you're embarking on a family vacation, jet-setting with friends or treating your spouse, your perfect stay is just a few clicks away with Expedia.
Are there any family-friendly resorts in Windham County?
Definitely, so round up the kiddos and start organizing that Windham County vacay! If Stratton is your chosen destination, stay at Mount Snow Grand Summit Resort. This 3-star resort is popular with traveling families, offering conveniences such as a playground and a sauna. Another terrific choice is The Black Bear Lodge at Stratton Mountain Resort. Also in Stratton, it has a 3-star rating and comes with childcare services and a sauna. There are plenty of fantastic things to do with your crew in Stratton. Stratton Golf School and Stratton Mountain Golf Course deliver a great day out.
Why book your resort in Windham County with Expedia?
Expedia will help you find your dream resort in Windham County. Traveling with the kids? Use our handy filters to search for properties with perks like a water park. If you have a certain budget, click on how much you want to spend and your preferred star rating. We'll help you find a suitable place whatever your style of travel or plans.
How can I find cheap resorts in Windham County?
An excellent way to get cheap resorts in Windham County is with Expedia's convenient filter tool. Fine-tune your search results by star rating, amenities and budget to take advantage of awesome prices in a few clicks.
What is there to do in Windham County near my resort?
Windham County offers so much to do and see, it can be difficult to work out where to start. If you're staying a while in Stratton, Stratton Golf School is a hit for both young and old.

Explore a world of travel with Expedia