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

Windham County Holiday Rentals

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Our top choices for Windham County holiday rentals

Outdoor pool, a heated pool

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 HK$534
HK$2,561 total
includes taxes & fees
5 Jul - 6 Jul
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

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, (169 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 HK$1,333
HK$2,846 total
includes taxes & fees
9 Jul - 10 Jul
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior

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 HK$1,372
HK$3,409 total
includes taxes & fees
29 Jun - 30 Jun
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Outdoor spa tub

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, (83 reviews)
The price is HK$2,737
HK$3,402 total
includes taxes & fees
29 Jun - 30 Jun
Long Trail House at Stratton Mountain Resort
Terrace/patio

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, (19 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is HK$1,372
HK$3,385 total
includes taxes & fees
14 Jul - 15 Jul
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Smart TV, fireplace, Netflix, streaming services

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
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is HK$838
HK$3,393 total
includes taxes & fees
29 Jun - 30 Jun
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Fridge, microwave, stovetop, coffee/tea maker

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (18 reviews)
"We had a great stay! Cabin is cozy and met all of our needs for the weekend. We loved exploring the nearby trails and shops. Our dogs loved it as well :) "
United States
Kelsey M.
Hiking Trails On-Site: Cozy Falls Brook Cabin
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is HK$667
HK$1,595 total
includes taxes & fees
30 Jun - 1 Jul
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (46 reviews)
"The property was beautiful and it truly felt like an escape. I"
United States
Kristina M.
The price is HK$1,035
HK$3,563 total
includes taxes & fees
29 Jun - 30 Jun
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Fridge, microwave, oven, stovetop

The MountainTop - Stratton & Mt Snow - Fire Pit

The MountainTop - Stratton & Mt Snow - Fire Pit
Stratton
10.0 out of 10, Exceptional, (9 reviews)
"Lovely place to stay. The stars truly are stunning. "
United States
Brenna G.
The price is HK$1,517
HK$3,274 total
includes taxes & fees
1 Jul - 2 Jul
The MountainTop - Stratton & Mt Snow - Fire Pit
Beach

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)
"Fire place was awesome! Great place to stay! Had everything in the kitchen we needed. All the beds were comfy! "
United States
Susan S.
The price is HK$635
HK$2,215 total
includes taxes & fees
8 Jul - 9 Jul
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (11 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$735
HK$3,230 total
includes taxes & fees
30 Jun - 1 Jul
Chalet Mount Snow/Stratton Skiing/hiking
Interior

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
Lobby

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 HK$585
HK$2,487 total
includes taxes & fees
30 Jun - 1 Jul
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Private kitchen

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, (2 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 HK$1,294
HK$2,450 total
includes taxes & fees
17 Jul - 18 Jul
The Studio with a View. Bring your dog, too!
Living area

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
10.0 out of 10, Exceptional, (1 review)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
The price is HK$1,389
HK$3,584 total
includes taxes & fees
15 Jul - 16 Jul
Stunning Glass House nestled in the Vermont wilderness!
Outdoor dining

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Townshend
8.0 out of 10, Very good, (1 review)
"Very nice place, an ideal VT cabin!"
United States
David D.
The price is HK$1,270
HK$2,635 total
includes taxes & fees
29 Jun - 30 Jun
Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Sauna

Magic Mountain Trailside Condo - Ski In / Ski Out

Magic Mountain Trailside Condo - Ski In / Ski Out
Londonderry
9.8 out of 10, Exceptional, (14 reviews)
"Nice and we enjoyed our stay"
United States
Gretchen H.
The price is HK$980
HK$2,393 total
includes taxes & fees
30 Jun - 1 Jul
Magic Mountain Trailside Condo - Ski In / Ski Out
TV, fireplace

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, (35 reviews)
"Appeared dated"
United States
John B.
The price is HK$585
HK$2,487 total
includes taxes & fees
29 Jun - 30 Jun
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Exterior

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 HK$585
HK$1,778 total
includes taxes & fees
29 Jun - 30 Jun
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
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

Four Columns Inn

Four Columns Inn

10/10 Excellent
"very nice place. creek out back, very fine pub and restaurant on site. Priced very fairly."
Michael 1-night trip
Posted 1 hour ago
Four Columns Inn