A wooden covered bridge over a river with stone walls on either side.

Windham County Vacation Rentals

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Top Cities in Windham County

Our top choices for Windham County vacation rentals

1. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (3 reviews)
"super cute tiny house! my partner and I had a wonderful time here. It's super close to downtown Brattleboro in a beautiful neighborhood"
United States
Anthony L.
The price is CA $103
CA $135 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Vermont Tiny Home Get Away

2. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is CA $109
CA $453 total
includes taxes & fees
Nov 23 - Nov 24
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

3. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (7 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is CA $143
CA $181 total
includes taxes & fees
Nov 18 - Nov 19
The Eagles Wing at The CHM - Private Apartment

4. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is CA $120
CA $377 total
includes taxes & fees
Nov 16 - Nov 17
Long Trail House 368 condo in Stratton Village, walk to the lifts

5. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is CA $140
CA $418 total
includes taxes & fees
Nov 29 - Nov 30
Cozy 3 bedroom condo 2.5 miles to Mount Snow

6. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy, set back and had all the amenities that you would need"
United States
Chelsea G.
The price is CA $100
CA $513 total
includes taxes & fees
Nov 16 - Nov 17
Chalet Mount Snow/Stratton Skiing/hiking

7. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
9.8 out of 10, Exceptional, (9 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is CA $167
CA $326 total
includes taxes & fees
Nov 18 - Nov 19
The Studio with a View. Bring your dog, too!

8. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
The price is CA $168
CA $519 total
includes taxes & fees
Nov 16 - Nov 17
Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

9. Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is CA $243
CA $409 total
includes taxes & fees
Nov 23 - Nov 24
Wellness Getaway with a Personal Sauna, and Private River Beach!

10. Fourth-floor Stratton Village studio with valley-view balcony

Fourth-floor Stratton Village studio with valley-view balcony
Stratton
The price is CA $133
CA $353 total
includes taxes & fees
Nov 16 - Nov 17
Fourth-floor Stratton Village studio with valley-view balcony

11. Founders Lodge condo at Stratton Mountain with gas fireplace

Founders Lodge condo at Stratton Mountain with gas fireplace
Stratton
8.0 out of 10, Very good, (1 review)
The price is CA $224
CA $587 total
includes taxes & fees
Nov 16 - Nov 17
Founders Lodge condo at Stratton Mountain with gas fireplace

12. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
Stratton
8.4 out of 10, Very good, (37 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is CA $120
CA $452 total
includes taxes & fees
Nov 16 - Nov 17
Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

13. 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, (85 reviews)
"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."
United States
Michael
The price is CA $507
CA $630 total
includes taxes & fees
Nov 17 - Nov 18
Long Trail House at Stratton Mountain Resort

14. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (66 reviews)
"Had a perfect, relaxing stay in this gorgeous spot. Everything was terrific. Highly recommend!"
United States
Wendy B.
The price is CA $233
CA $414 total
includes taxes & fees
Nov 17 - Nov 18
Family Friendly Hilltop House In Putney Vermont

15. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is CA $246
CA $798 total
includes taxes & fees
Nov 16 - Nov 17
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

16. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (176 reviews)
"Very pet friendly & nice country location. Host was responsive & helpful."
United States
Neil S.
The price is CA $243
CA $523 total
includes taxes & fees
Nov 16 - Nov 17
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

17. Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is CA $199
CA $377 total
includes taxes & fees
Nov 16 - Nov 17
Cozy cabin in charming Londonderry

18. Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex

Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex
Dover
9.6 out of 10, Exceptional, (5 reviews)
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
United States
Douglas D.
The price is CA $194
CA $584 total
includes taxes & fees
Nov 16 - Nov 17
Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex

19. Cozy Cedar Cabin 8 Min to Mount Snow

Cozy Cedar Cabin 8 Min to Mount Snow
Dover
The price is CA $248
CA $888 total
includes taxes & fees
Nov 22 - Nov 23
Cozy Cedar Cabin 8 Min to Mount Snow

20. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.4 out of 10, Exceptional, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is CA $245
CA $706 total
includes taxes & fees
Nov 30 - Dec 1
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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

Find out more about Windham County

Everything you need to know about Windham County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windham County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windham County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windham County vacation rentals we have selected for you start as low as CA $135 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windham County rentals

At Expedia, we put the best Windham County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windham County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.