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 $87
CA $445 total
includes taxes & fees
Oct 26 - Oct 27
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A calm lake with a wooden boat on the shore.

2. 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 wooden house with a porch lit by string lights, surrounded by snow.

3. 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 $186
CA $650 total
includes taxes & fees
Oct 6 - Oct 7
Chalet Mount Snow/Stratton Skiing/hiking
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

4. 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 $600 total
includes taxes & fees
Oct 5 - Oct 6
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A red house with a covered porch and a chimney.

5. 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 $241
CA $525 total
includes taxes & fees
Oct 19 - Oct 20
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

6. 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 bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

7. 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 $208 total
includes taxes & fees
Oct 6 - Oct 7
The Eagles Wing at The CHM - Private Apartment
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

8. 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 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 spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.

10. 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 $188
CA $662 total
includes taxes & fees
Oct 27 - Oct 28
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

11. 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 $447 total
includes taxes & fees
Oct 4 - Oct 5
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A room with white paneled walls, a wooden bench, a teal cushion, a vase with flowers, a framed picture, and a shelf with books and a small electronic device.

12. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is CA $109
CA $155 total
includes taxes & fees
Oct 30 - Oct 31
Cozy Vermont Tiny Home Get Away
A garden with a wooden pergola, purple flowers, and a river view.

13. 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 $375 total
includes taxes & fees
Oct 28 - Oct 29
Family Friendly Hilltop House In Putney Vermont
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

14. 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 $241
CA $426 total
includes taxes & fees
Oct 20 - Oct 21
Wellness Getaway with a Personal Sauna, and Private River Beach!
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

15. 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 $317 total
includes taxes & fees
Oct 8 - Oct 9
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

16. 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 $296
CA $745 total
includes taxes & fees
Oct 4 - Oct 5
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

17. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (20 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is CA $270
CA $640 total
includes taxes & fees
Oct 27 - Oct 28
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A hallway with a bench, a wall-mounted towel rack, and a door leading to an outdoor area.

18. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (11 reviews)
"Loved this place so much! Adorable spot, quaint but has everything you need. Loved the luxury details. "
United States
Carly L.
The price is CA $278
CA $714 total
includes taxes & fees
Nov 1 - Nov 2
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

19. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
The price is CA $262
CA $692 total
includes taxes & fees
Oct 5 - Oct 6
Modern Mount Snow Gnarvana - Steps to Carinthia
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

20. 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 $499 total
includes taxes & fees
Oct 11 - Oct 12
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
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
"We absolutely enjoyed the property. Our room had a fireplace. The bed was very comfortable. There was a pool table and games to play. One of the best places we have stayed at!"
James 1-night trip
Posted 3 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 $317 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.