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

Vacation Rentals in Windham County

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Top Cities in Windham County

A forest with autumn foliage reflecting in a calm lake.
Vacation RentalsVacation Rentals

Stratton

Stratton

Our top choices for Windham County vacation rentals

A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

1. 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 ￥56,150
￥69,795 total
includes taxes & fees
Oct 25 - Oct 26
Long Trail House at Stratton Mountain Resort
A covered outdoor seating area with two chairs and a table, overlooking a snowy forest.

2. Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
Hiking Trails On-site: Cozy Falls Brook Cabin
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 ￥14,235
￥46,470 total
includes taxes & fees
Oct 29 - Oct 30
Cozy 3 bedroom condo 2.5 miles to Mount Snow
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)
"Great property and location. Communications with host excellent. Love the privacy and availability of firewood."
United States
Rod M.
The price is ￥16,766
￥67,025 total
includes taxes & fees
Nov 11 - Nov 12
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A wooden barrel structure with a staircase and railing, surrounded by a forest.

5. Dover Mountain Retreat with Hot Tub Near Mt. Snow

Dover Mountain Retreat with Hot Tub Near Mt. Snow
Dover
10.0 out of 10, Exceptional, (11 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
The price is ￥49,188
￥112,189 total
includes taxes & fees
Nov 1 - Nov 2
Dover Mountain Retreat with Hot Tub Near Mt. Snow
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

6. 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 ￥9,737
￥49,789 total
includes taxes & fees
Oct 26 - Oct 27
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

7. 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 ￥25,325
￥45,028 total
includes taxes & fees
Nov 4 - Nov 5
Wellness Getaway with a Personal Sauna, and Private River Beach!
A red house with a covered porch and a chimney.

8. 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, (173 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 ￥26,889
￥57,397 total
includes taxes & fees
Oct 26 - Oct 27
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A garden with a wooden pergola, purple flowers, and a river view.

9. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (65 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 ￥22,776
￥43,756 total
includes taxes & fees
Oct 27 - Oct 28
Family Friendly Hilltop House In Putney Vermont
A wooden house with a porch lit by string lights, surrounded by snow.

10. 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 ￥18,525
￥69,864 total
includes taxes & fees
Nov 8 - Nov 9
Chalet Mount Snow/Stratton Skiing/hiking
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

11. 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 ￥26,908
￥67,429 total
includes taxes & fees
Nov 3 - Nov 4
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

12. 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 ￥23,093
￥63,713 total
includes taxes & fees
Nov 11 - Nov 12
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

13. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is ￥31,001
￥90,503 total
includes taxes & fees
Oct 25 - Oct 26
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

14. 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, (37 reviews)
"Great space, great location!"
United States
Jason S.
The price is ￥27,189
￥75,943 total
includes taxes & fees
Oct 26 - Oct 27
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

15. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.8 out of 10, Excellent, (6 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
The price is ￥57,574
￥102,039 total
includes taxes & fees
Oct 26 - Oct 27
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
A modern kitchen with large windows, a built-in dishwasher, and a refrigerator.

16. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
9.8 out of 10, Exceptional, (9 reviews)
"A beautiful, clean, and cozy stay. The modern space was bright and well-equipped with everything we needed, and the hot tub made it especially relaxing."
United States
Nicole H.
The price is ￥70,749
￥124,944 total
includes taxes & fees
Nov 9 - Nov 10
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Interior

17. 3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails

3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
Halifax
10.0 out of 10, Exceptional, (1 review)
"This place was honestly amazing. All secluded and even with how far away the cabin was from the main road the cabin had everything you could imagine and everything felt perfect. 10/10 would return"
United States
Justin M.
The price is ￥27,616
￥76,989 total
includes taxes & fees
Oct 25 - Oct 26
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
An indoor swimming pool with a tiled floor, a pool table, and a bar area.

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 ￥21,551
￥68,678 total
includes taxes & fees
Oct 23 - Oct 24
Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex
A spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.

19. 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 ￥19,474
￥71,871 total
includes taxes & fees
Nov 9 - Nov 10
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A two-story white house with a red door, surrounded by autumn foliage and a stone wall.

20. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is ￥24,358
￥31,099 total
includes taxes & fees
Nov 1 - Nov 2
The Eagles Wing at The CHM - Private Apartment
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

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

10/10 Excellent
"Clean room, but very old and needs updating. TV had Netflix and Prime."
Nazia 2-night trip
Posted 14 hours ago
Travelodge by Wyndham Brattleboro VT

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Vacation Apartments in Windham County

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