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Best Resorts in Windham County

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Sep 4 - Sep 6
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Sep 11 - Sep 13
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Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

Top Cities in Windham County

A calm lake reflecting a forest with autumn foliage.
ResortsResorts

Brattleboro

Brattleboro

Our top choices for Windham County resorts

Exterior

1. Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property
3.0 star property
West Dover
8.6 out of 10, Excellent, (306 reviews)
"Room was clean, the staff was friendly and helpful. We would stay again."
United States
Daniel
$161 nightly
The price is $176
Sep 29 - Sep 30
Total with taxes and fees
Grand Summit Resort, A Vail Resorts Property
Room

2. 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
$142 nightly
The price is $156
Sep 29 - Sep 30
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
Exterior

3. 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.
$411 nightly
The price is $449
Aug 30 - Aug 31
Total with taxes and fees
King with Bunk Bed- 2nd floor in Historic Inn
Interior

4. 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.
$489 nightly
The price is $535
Aug 30 - Aug 31
Total with taxes and fees
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Exterior

5. 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
$437 nightly
The price is $478
Aug 30 - Aug 31
Total with taxes and fees
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
Exterior

6. 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.
$437 nightly
The price is $478
Aug 30 - Aug 31
Total with taxes and fees
Deluxe King, kitchenette, fireplace
Exterior

7. 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
$411 nightly
The price is $449
Aug 30 - Aug 31
Total with taxes and fees
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
Interior

8. Luxury King with balcony

Luxury King with balcony
West Dover
$411 nightly
The price is $449
Aug 30 - Aug 31
Total with taxes and fees
Luxury King with balcony
Room

9. 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.
$372 nightly
The price is $405
Aug 30 - Aug 31
Total with taxes and fees
Deluxe 2xQueen- 2nd floor in Historic Inn
Interior

10. 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.
$411 nightly
The price is $449
Aug 30 - Aug 31
Total with taxes and fees
Deluxe King Room w/fireplace and separate entrance
Dining

11. 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.
$411 nightly
The price is $449
Aug 30 - Aug 31
Total with taxes and fees
Deluxe King Room w/pull-out love seat and fireplace
Room

12. Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn
West Dover
8.0 out of 10, Very Good, (1 review)
$372 nightly
The price is $405
Aug 30 - Aug 31
Total with taxes and fees
Deluxe 2xQueen in Historic Inn
Room

13. 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.
$411 nightly
The price is $449
Aug 31 - Sep 1
Total with taxes and fees
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
Exterior

14. Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
$411 nightly
The price is $449
Aug 30 - Aug 31
Total with taxes and fees
Deluxe King - 2nd floor in Historic Inn
Exterior

15. 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.
$411 nightly
The price is $449
Aug 30 - Aug 31
Total with taxes and fees
Luxury King w/balcony, accessible
Interior

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

Deluxe Queen Suite with pull-out love seat, private entrance
Dover
$372 nightly
The price is $405
Aug 30 - Aug 31
Total with taxes and fees
Deluxe Queen Suite with pull-out love seat, private entrance
Exterior

17. Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
$411 nightly
The price is $449
Aug 30 - Aug 31
Total with taxes and fees
Deluxe King - 2nd floor in Historic Inn
Room

18. 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.
$437 nightly
The price is $478
Aug 30 - Aug 31
Total with taxes and fees
Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
Room

19. Deluxe 2xQueen & fireplace

Deluxe 2xQueen & fireplace
Dover
10.0 out of 10, Exceptional, (1 review)
"Beautiful Inn however, the fridge should be lifted off the floor. It’s too low. A small broom and dust pan would be nice to sweep up the dirt that treks in from the dirt parking lot and walk ways. Upgrade full size beds to at least two Queen size beds."
United States
Christina R.
$372 nightly
The price is $405
Aug 30 - Aug 31
Total with taxes and fees
Deluxe 2xQueen & fireplace
Exterior

20. 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.
$437 nightly
The price is $478
Aug 30 - Aug 31
Total with taxes and fees
Deluxe King, 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.
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Top Windham County Hotel Reviews

Chalet 239

Chalet 239

10/10 Excellent
"Perfect boutique stay"
Michelle 1-night trip
Posted less than an hour ago
Chalet 239

Find out more about Windham County

Windham County Resorts information

Number of reviews
1,042
Accommodation
26 Resorts
Lowest Price
$156
Highest Price
$535

Frequently asked questions

How much do resorts in Windham County cost?
Rates for resorts in Windham County range between $156 and $535 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