Top Cottages in Windham County in 2026

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

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Top Cities in Windham County

A calm lake reflecting a forest with autumn foliage.

A snow-covered landscape with a bench and trees.

Our top choices for Windham County cottages

1. The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Chester

Anonymous traveler

2. West Dover Home - 3 Miles to Mount Snow Resort!

West Dover

Jacqueline

3. Vermont Country Cottage (Near Village)

Londonderry

Joe A.

4. Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Wilmington

Bronwyn

5. Rare new Home on Lake Whitingham. Semi-priv beach

Wilmington

michael r.

6. 4 Mi to Lake Raponda! Secluded Family Cottage

Wilmington

7. 3 Mi to Mount Snow: Spacious West Dover Home

West Dover

AED 2,400 total

includes taxes & fees

16 Aug - 17 Aug

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

Brattleboro

sarah

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Top Windham County Hotel Reviews

Inn At Mount Snow

10/10 Excellent

"i love ❤️ 10/10"

Hideaway Inn Mt. Snow

8/10 Good

"The style and aesthetic of the Hideaway Inn was unique and cool. The attention to detail as far as honing in on the Vermont ski aesthetic along with the retro record player in each room as well as common rooms was also pleasant. The room itself was small for my family of 4 plus a dog, but the outdoor balcony space as well as the variety of shared spaces was helpful. The Inn had a play space geared more towards young children as well as an upstairs loft geared for older children, with board games and puzzles, or adults. My young children loved the play area; it could have used a bit more lighting though. There was only one innkeeper on staff plus a text number should there be any needs or emergencies. The text number was not so hopeful for when we needed a plunger. There is a supplies closet that had towels, bottle openers, extra tissues, toilet paper, etc. That was helpful. When booking our room, I was under the impression all two bed rooms had a bathtub in the bathroom. Ours did not, and in an attempt to switch rooms, it was not possible due to an incoming check in later in the week which would have required several re-bookings, as per the innkeeper. We made it work with our young children. The space outside of the Inn was beautiful with an outdoor patio, fire pit, and a pool. There was a coffee machine and water machine. On our last two days, however, the coffee machine did not work."

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"Rooms and beds were very comfortable. Shower was great - everything was great except the rugs inside the rooms are old and felt damp always. Maybe it was more about the humidity but they just felt gross. I really enjoyed the hot tub, sauna and being able to go up to the village which had so many wonderful restaurants, bars and shops. I saw a Neil Young tribute band and that was so much fun. Carpets aside, I would stay here again I think they just need updating. It is a perfect location with many amenities."

Latchis Hotel

8/10 Good

"In an old Theater building. Definitely has character and cool features. We arrived too late for the movies, but still fun. In central Brattleboro which has some interesting shops, but is suffering from homelessnes and mental illness/drug use. Didnt really feel unsafe and we walked a few blocks to a fun restaurant with good food & karioke. Person at desk was lovely and helpful. Room was ok- a little dated and could be cleaner."

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Cottages in Windham County

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Treat yourself

Be picky

Check prices for these dates

Top Cities in Windham County

Brattleboro

Londonderry

Our top choices for Windham County cottages

1. The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

2. West Dover Home - 3 Miles to Mount Snow Resort!

3. Vermont Country Cottage (Near Village)

4. Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

5. Rare new Home on Lake Whitingham. Semi-priv beach

6. 4 Mi to Lake Raponda! Secluded Family Cottage

7. 3 Mi to Mount Snow: Spacious West Dover Home

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

9. Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

10. Cottage-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK

11. Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

12. Wilmington Vacation Rental Near Hiking and Skiing!

13. 10 Mi to Mt Snow! Grand Estate Built to Entertain

14. Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

15. Charming Putney Home: Porch, Grill & Hiking Trails

16. Jacksonville Cabin w/ Wraparound Deck & Views

17. 'mount Pine' Winter Retreat Near the Green Mtns!

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

19. Honey Paws Inn: Wilmington Home 6 Mi to Mount Snow

20. West Dover Vacation Rental w/ Hot Tub Near Mt Snow

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Top Windham County Hotel Reviews

Inn At Mount Snow

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