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 spa tub

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, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is HK$2,465
HK$3,064 total
includes taxes & fees
19 Aug - 20 Aug
Long Trail House at Stratton Mountain Resort
Exterior

2. 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, (170 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$1,334
HK$2,909 total
includes taxes & fees
17 Aug - 18 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Property grounds

3. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,356
HK$2,494 total
includes taxes & fees
1 Sept - 2 Sept
Family Friendly Hilltop House In Putney Vermont
Outdoor pool, a heated pool

4. 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$481
HK$2,405 total
includes taxes & fees
17 Aug - 18 Aug
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Interior

5. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is HK$2,982
HK$5,128 total
includes taxes & fees
17 Aug - 18 Aug
3 Mi to Mount Snow: Spacious West Dover Home
Dining

6. The MountainTop | Stratton & Mt Snow | Fire Pit

The MountainTop | Stratton & Mt Snow | Fire Pit
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Lovely place to stay. The stars truly are stunning. "
United States
Brenna G.
The price is HK$2,110
HK$4,795 total
includes taxes & fees
28 Aug - 29 Aug
The MountainTop | Stratton & Mt Snow | Fire Pit
Terrace/patio

7. 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$1,530
HK$3,600 total
includes taxes & fees
1 Sept - 2 Sept
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Coffee/tea maker, fridge, microwave, oven

8. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is HK$3,637
HK$9,129 total
includes taxes & fees
17 Aug - 18 Aug
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Coffee/tea maker, fridge, microwave, stovetop

9. 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, (7 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 HK$3,510
HK$6,199 total
includes taxes & fees
19 Aug - 20 Aug
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Terrace/patio

10. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
West Dover
10.0 out of 10, Exceptional, (1 review)
"All good. "
United States
ken g.
The price is HK$2,480
HK$5,400 total
includes taxes & fees
17 Aug - 18 Aug
3 Mi to Mount Snow: Spacious West Dover Home
Property grounds

11. 10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK

10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
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 HK$2,134
HK$5,162 total
includes taxes & fees
25 Aug - 26 Aug
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
Coffee/tea maker, fridge, microwave, oven

12. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (7 reviews)
"Perfect spot for a family ski vacation! Thanks you for behind a great host!"
United States
Andrew B.
The price is HK$4,316
HK$7,856 total
includes taxes & fees
17 Aug - 18 Aug
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Exterior

13. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (14 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$1,068
HK$3,660 total
includes taxes & fees
31 Aug - 1 Sept
Chalet Mount Snow/Stratton Skiing/hiking
Beach

14. 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$664
HK$2,275 total
includes taxes & fees
30 Aug - 31 Aug
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Exterior

15. Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
10.0 out of 10, Exceptional, (46 reviews)
"Awesome home. Had a great time with the family. Owners were easy to get in touch with."
United States
william k.
The price is HK$2,331
HK$4,886 total
includes taxes & fees
17 Aug - 18 Aug
Summer Escape Near Lakes, Trails & Mt Snow
Terrace/patio

16. A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
Dover
10.0 out of 10, Exceptional, (21 reviews)
"Excellent location and really fun common spaces made this a great choice for our ski vacation. The hosts were super responsive especially when we got a big snow storm and the driveway was plowed. "
United States
Victoria R.
The price is HK$1,609
HK$4,708 total
includes taxes & fees
8 Sept - 9 Sept
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
Interior

17. Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Great location, comfortable and spacious living room and bedrooms. "
United States
Emma C.
The price is HK$1,977
HK$5,090 total
includes taxes & fees
17 Aug - 18 Aug
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Living area

18. 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
8.4 out of 10, Very good, (5 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 HK$2,571
HK$4,663 total
includes taxes & fees
30 Aug - 31 Aug
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Smart TV, fireplace, video games, DVD player

19. Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (62 reviews)
"A fantastic spot for a cozy, small town vibe. Highly recommend"
United States
Nicholas G.
The price is HK$2,374
HK$6,008 total
includes taxes & fees
17 Aug - 18 Aug
Walk To Town, Hottub, Firepit, Games, Mt Snow
Interior

20. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (24 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
The price is HK$1,839
HK$4,871 total
includes taxes & fees
18 Aug - 19 Aug
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
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

Deerfield Valley Inn

Deerfield Valley Inn

10/10 Excellent
"Beautiful 150 y/o property with lovely community rooms and a nice outdoor sitting area"
Carol 2-night trip
Posted 1 hour ago
Deerfield Valley Inn