Windham County Vacation Home Rentals from CA $409: 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 calm lake reflecting a forest with autumn foliage.

Our top choices for Windham County vacation homes

1. Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Pikes Falls

Christina P.

2. Family Friendly Hilltop House In Putney Vermont

Putney

Susan O.

CA $409 total

includes taxes & fees

Sep 1 - Sep 2

3. Bright three-level home with water views, jetted tub, firepit, and pool table

Jacksonville

Brian E.

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

West Dover

Lisette B.

5. SPLISH SPLASH! Explore Vermont!

Londonderry

Lily M.

6. Red Brick Retreat - 8br 6ba Hot Tub Sauna Home Gym

Londonderry

Anonymous traveller

7. Spacious Riverfront Home 7 Minutes to Stratton!

Jamaica

Eric P.

8. Beautiful 4 BR Townhome minutes from Mt Snow

West Dover

Dave F.

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Top Windham County Hotel Reviews

Travelodge by Wyndham Brattleboro VT

10/10 Excellent

"As a single tired woman traveling, I was a little leery of Brattleboro, the gent who checked me in was very pleasant, the room was fine for a one nighter! My only “bummer” was that the coffee wasn’t working. But there was enough food all around the area to accommodate that !"

Four Columns Inn

10/10 Excellent

"We couldn’t have been happier with our stay at the four columns. Our room was beautiful as are the grounds. The end is surrounded by well keptGardens with lovely flowers and there are lots of places to sit outside and enjoy them. Staff was gracious. The breakfast delicious we used to live in Vermont and came back for a visit for a wedding and decided to stay at the Inn. We had eaten dinner there many times, but never had the opportunity to enjoy an overnight until now. We are so glad we came back and so glad we chose the four columns in for our getaway."

Latchis Hotel

8/10 Good

"The art deco building is gorgeous. I applaud the non-profit organization that saved, renovated and maintains this exceptional building. I very much appreciated the original bathroom fixtures. The hotel really gives you a taste of what it might have been like to travel back in the 1930-40s. On the downside, my experience was not the best: When I arrived, the front desk lady said something like: "I'll be right with you". Two minutes later, she came to the front desk joking about having problems with her Emails. Not acceptable! You should pause your Email activity when someone is waiting in the lobby. My wife and I were looking forward to a drink at the hotel bar. The website indicated that the bar was open, and a note on the door confirmed. There was nobody there. Money and a lady's purse were spread out on the bar. We were told at the front desk that the people running the bar for them decided not to open that evening. Not acceptable. The next morning I took a lukewarm shower, as it took about ten minutes for the water to become warm enough, By then I was done and my feet were in about 5" of dirty water because the drain was clogged. We were also told that if we did not turn in our brass key, they would charge us $75 to replace it. When walked down to the lobby, there was a sign stating that front desk duty started at 9:00."

Find out more about Windham County

Windham County Vacation Homes information

Number of reviews	623
Accommodation	448 Vacation Homes
Lowest Price	CA $409
Highest Price	CA $409

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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

Brattleboro

Our top choices for Windham County vacation homes

1. Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

2. Family Friendly Hilltop House In Putney Vermont

3. Bright three-level home with water views, jetted tub, firepit, and pool table

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

5. SPLISH SPLASH! Explore Vermont!

6. Red Brick Retreat - 8br 6ba Hot Tub Sauna Home Gym

7. Spacious Riverfront Home 7 Minutes to Stratton!

8. Beautiful 4 BR Townhome minutes from Mt Snow

9. Spyglass village- Golf & Ski

10. Quiet Country 2 Bedroom Home Near Bellows Falls & Walpole — Easy I-91 Access

11. Woodsy Getaway! Shuttle or Ski-home from Mt. Snow

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

13. Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing

14. Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

15. The Jelly Mill-A Peaceful River Retreat

16. Outdoor Enthusiasts Paradise in Beautiful Vermont!

17. Cozy cottage tucked away in the woods

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

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

20. Ski In / Ski Out 4BR / 3BA Private Hot Tub and shared pool