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

A canoe on calm water with a forested hill in the background.
Vacation RentalsVacation Rentals

West Dover

West Dover
A forest with autumn foliage reflecting in a calm lake.
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Stratton

Stratton

Our top choices for Windham County vacation rentals

A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

1. 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 $88
CA $446 total
includes taxes & fees
Oct 28 - Oct 29
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A compact bedroom with a bed, a window, and a small kitchenette.

2. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is CA $102
CA $148 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Vermont Tiny Home Get Away
A calm lake with a wooden boat on the shore.

3. 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 $131
CA $423 total
includes taxes & fees
Oct 13 - Oct 14
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

4. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is CA $106
CA $366 total
includes taxes & fees
Oct 5 - Oct 6
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

5. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is CA $106
CA $318 total
includes taxes & fees
Oct 7 - Oct 8
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

6. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is CA $155
CA $207 total
includes taxes & fees
Oct 6 - Oct 7
The Eagles Wing at The CHM - Private Apartment
A garden with a wooden pergola, purple flowers, and a river view.

7. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is CA $189
CA $378 total
includes taxes & fees
Oct 20 - Oct 21
Family Friendly Hilltop House In Putney Vermont
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

8. 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 $235
CA $413 total
includes taxes & fees
Nov 2 - Nov 3
Wellness Getaway with a Personal Sauna, and Private River Beach!
A wooden interior with a kitchen, bar area, and dining space.

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

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (5 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 $183
CA $377 total
includes taxes & fees
Oct 5 - Oct 6
The Studio with a View. Bring your dog, too!
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

10. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (48 reviews)
"Once we got to know the fireplace, it was a wonderful addition to a very cozy cabin. The house felt loved and each different room had different touches of character and magic. We absolutely loved our stay. "
United States
Sarah K.
The price is CA $151
CA $599 total
includes taxes & fees
Oct 5 - Oct 6
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

11. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
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 $149
CA $500 total
includes taxes & fees
Oct 11 - Oct 12
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
A red house with a covered porch and a chimney.

12. 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, (172 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is CA $242
CA $519 total
includes taxes & fees
Oct 12 - Oct 13
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

13. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (36 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 $106
CA $448 total
includes taxes & fees
Oct 5 - Oct 6
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

14. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is CA $208
CA $573 total
includes taxes & fees
Oct 5 - Oct 6
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

15. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very good, (1 review)
The price is CA $199
CA $576 total
includes taxes & fees
Oct 4 - Oct 5
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
A spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.

16. 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, (28 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is CA $184
CA $658 total
includes taxes & fees
Oct 27 - Oct 28
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

17. 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, (84 reviews)
"Nice place and great location!!!"
United States
William
The price is CA $505
CA $628 total
includes taxes & fees
Oct 4 - Oct 5
Long Trail House at Stratton Mountain Resort
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

18. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (35 reviews)
"Great space, great location!"
United States
Jason S.
The price is CA $283
CA $730 total
includes taxes & fees
Oct 26 - Oct 27
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A wooden house with a porch lit by string lights, surrounded by snow.

19. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (16 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is CA $174
CA $635 total
includes taxes & fees
Oct 6 - Oct 7
Chalet Mount Snow/Stratton Skiing/hiking
A living room with a television, sofa, and coffee table.

20. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (5 reviews)
"Host was very accommodating and understanding. Really smooth communication with the host. And the location couldn’t have been much better."
United States
Ernesto M.
The price is CA $294
CA $693 total
includes taxes & fees
Oct 27 - Oct 28
Long Trail House South Wing 2B2B Condo
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

Inn At Mount Snow

Inn At Mount Snow

10/10 Excellent
"Clean room, friendly staff, nice views. Best, though, is the relaxing decor, and ambience of the downstairs common area. Very nice. Breakfast is continental and rather simple (ie. cold cereal, yogurt, muffins, fruits) but did the trick for us. Enjoyed our stay. Thank you!"
Lionel 2-night trip
Posted 2 hours ago
Inn At Mount Snow

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 $318 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.