Windham County Vacation Home Rentals from CA $363: Search Top Private Vacation Homes for Rent

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

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Top Cities in Windham County

A canoe on calm water with a forested hill in the background.

Our top choices for Windham County vacation homes

A living room with a stone fireplace, a flat-screen TV mounted above it, a sofa, and a sliding glass door leading to an outdoor patio.

1. 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Dover

Cindy D.

A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

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

Dover

jim f.

CA $1,509 total

includes taxes & fees

Nov 8 - Nov 9

A spacious living room with a fireplace, a dining area, and a kitchen with wooden cabinets and a microwave.

3. Book the Lemondrop for your Thanksgiving and experience Vermont’s Fall Magic

Dover

Alexander H.

CA $844 total

includes taxes & fees

Nov 9 - Nov 10

A large, two-story house with a covered porch and string lights.

4. 5 Bdrm Lakehouse, sleeps 18, private dock, hot tub, 15 minutes to Mount Snow

Wilmington

Elizabeth C.

A wooden door leading to a deck with a view of a lake and mountains.

5. Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Wilmington

Brendan S.

A room with a stone fireplace, wooden beams, and large windows.

6. Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington

Alicia M.

A pool area with a wooden deck, surrounded by a wooden fence, and a view of a forested landscape with hills in the background.

7. Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Townshend

karen g.

A dining area with a table and chairs, a view of the outdoors, and a patterned rug.

8. The Jelly Mill-A Peaceful River Retreat

Guilford

Jayvonte M.

A covered wooden deck with wicker furniture and a glass table, overlooking a forested area.

9. Beautiful, private log cabin with huge, relaxing screened porch

Townshend

Nina G.

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

10. Long Trail House 368 condo in Stratton Village, walk to the lifts

Stratton

CA $363 total

includes taxes & fees

Nov 8 - Nov 9

A log cabin interior with a high ceiling, wooden beams, a large arched window, and a cozy living area with furniture.

11. Chimney Hill log house with wraparound deck and clubhouse pool

Wilmington

Ruth S.

A rustic interior with exposed wooden beams, a cozy seating area with a sofa and coffee table, and a staircase leading to an upper level.

12. Vermont Chalet w/ Sweeping Mountain Views

Dover

A residential area with a house, a driveway, and a tennis court surrounded by dense forest.

13. Spacious Corner Townhouse next to Mt. Snow! Private hot tub!

Dover

Carl

A living room with a sofa, armchair, and fireplace.

14. Potter's Place, bordered by Jamaica State Park, with gas fireplace

East Jamaica

Susan C.

A cozy room with a fireplace, a window with a view of a snowy landscape, and a ski-themed pillow on the bed.

15. MOUNT SNOW CHALET/LOFT CONDO

Dover

Andrea L.

A spacious living room with a stone fireplace, large windows, and a modern sofa set.

16. Spyglass village- Golf & Ski

Wilmington

Emmanouhl T.

A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

17. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

Stratton

Brian G.

CA $1,387 total

includes taxes & fees

Nov 10 - Nov 11

A child standing on a wooden deck with a view of a lake and forested hills in the background.

18. Beaver's Bend Lakefront Retreat ~16 mi to Slopes & Pet Friendly!

Whitingham

Louise P.

A modern house with a hot tub on the deck, surrounded by string lights and a deck chair.

19. Bears Den Chalet | Ski Home, Ski Shuttle, Hot Tub!

West Dover

Lauren F.

A wooden cabin with a balcony and a staircase leading to a second floor.

20. South Londonderry Home, Walk to Magic Mtn Ski Area

S Londonderry

Dean N.

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Top Windham County Hotel Reviews

The Putney Inn

10/10 Excellent

"I got there a little early and was able to check in. Room was great. Price was great. Recommended if you're headed to the Putney/Brattleboro area."

Hideaway Inn Mt. Snow

10/10 Excellent

"The room was small and simple, but nicely decorated, including a record player with a vinyl album (cover, at least; didn't check for actual vinyl). The room was warm and the place was quiet when I stayed, which was off-season. I've been pulling into the parking lot of this place for five years now (MOOver), so staying there was interesting for me. I stayed there during a HAZMAT spill that closed Woodford Mtn for a couple days. Of special note, this is the ONLY hotel I've ever stayed at that had a sleep/sound machine in the room. I ALWAYS take one with me when traveling, but this was a last minute decision, so I would've had to pull up something on my phone, but there was a nice sound machine on the nightstand and I used it. Those are so helpful when staying in hotels/inns."

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent

"A one-night stay. It had everything we needed. Not fancy, but it was all there, clean and bright. It is right next to the Interstate, but we could not hear any road traffic, so for the win. The morning breakfast scene is complete. The staff was very polite and accommodating."

Find out more about Windham County

Windham County Vacation Homes information

Number of reviews	838
Accommodation	448 Vacation Homes
Lowest Price	CA $363
Highest Price	CA $1,509

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Windham County Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Top Cities in Windham County

West Dover

Our top choices for Windham County vacation homes

1. 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

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

3. Book the Lemondrop for your Thanksgiving and experience Vermont’s Fall Magic

4. 5 Bdrm Lakehouse, sleeps 18, private dock, hot tub, 15 minutes to Mount Snow

5. Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

6. Beautiful Custom Built Timber Frame Home, Sleeps 11

7. Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

8. The Jelly Mill-A Peaceful River Retreat

9. Beautiful, private log cabin with huge, relaxing screened porch

10. Long Trail House 368 condo in Stratton Village, walk to the lifts

11. Chimney Hill log house with wraparound deck and clubhouse pool

12. Vermont Chalet w/ Sweeping Mountain Views

13. Spacious Corner Townhouse next to Mt. Snow! Private hot tub!

14. Potter's Place, bordered by Jamaica State Park, with gas fireplace

15. MOUNT SNOW CHALET/LOFT CONDO

16. Spyglass village- Golf & Ski

17. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

18. Beaver's Bend Lakefront Retreat ~16 mi to Slopes & Pet Friendly!

19. Bears Den Chalet | Ski Home, Ski Shuttle, Hot Tub!

20. South Londonderry Home, Walk to Magic Mtn Ski Area

Find vacation rentals that suit your style

Top Windham County Hotel Reviews

The Putney Inn

Find out more about Windham County

Windham County Vacation Homes information

Explore a world of travel with Expedia