Windham County Hotels with a Pool from $93

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.

Check availability on Windham County Hotels with a Pool

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Our top choices for Windham County hotels with a pool

1. Colonial Motel

Brattleboro

Splash into a Vermont mountain getaway with indoor pools and a rejuvenating hot tub sanctuary.

$84 nightly

Aug 24 - Aug 25

Total with taxes and fees

2. Hampton Inn Brattleboro

Brattleboro

Immerse in rejuvenating waters at this mountain-adjacent hotel featuring a pristine indoor pool and relaxing hot tub sanctuary.

$114 nightly

Sep 8 - Sep 9

Total with taxes and fees

3. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Splash into family fun with a year-round indoor pool perfect for kids at this rural Vermont retreat.

$178 nightly

Sep 13 - Sep 14

Total with taxes and fees

4. Quality Inn & Conference Center Brattleboro North

Brattleboro

Indoor pool brings all-weather swimming to your mountain getaway with arcade games and cozy lobby fireplace.

Seasonal outdoor pool, pool umbrellas, sun loungers

5. Deerhill Inn

West Dover

Savor summer days at this Vermont bed & breakfast with a serene seasonal pool, surrounded by loungers and majestic mountain views.

6. Econo Lodge Brattleboro South

Brattleboro

Refresh poolside with a seasonal summer dip at this Vermont motel for adults only.

$89 nightly

Aug 30 - Aug 31

Total with taxes and fees

7. Black Mountain Inn

Brattleboro

Refreshing poolside retreat in Black Mountain with seasonal swimming and scenic garden views.

$131 nightly

Sep 1 - Sep 2

Total with taxes and fees

8. Blue Gentian Lodge at Magic Mountain

Londonderry

Swim in the sunlit mountain waters at this alpine retreat's seasonal outdoor pool nestled in picturesque Vermont.

$149 nightly

Aug 26 - Aug 27

Total with taxes and fees

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Top Windham County Hotel Reviews

Chalet 239

10/10 Excellent

"Had a great stay. Comfortable bed, nice amenities."

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."

Deerfield Valley Inn

8/10 Good

"We returned to this place on a quick 2-day/last minute get away. Owner is new from last time. Nice people; helpful and made a very good breakfast. Only issue we really had was the plumbing. Our room had some kind of venting issue with the sink/toilet/shower. Toilet bubbled and would go down at times; sink would go slow/stop at times; shower also stopped up and went down very slow. Told the owner about it and hopefully they can get it fixed. But overall, pleasant stay."

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Top Cities in Windham County

Brattleboro

West Dover

Wilmington

Stratton

Londonderry

Jamaica

Putney

Check availability on Windham County Hotels with a Pool

Our top choices for Windham County hotels with a pool

1. Colonial Motel

2. Hampton Inn Brattleboro

3. Holiday Inn Express Hotel & Suites Brattleboro by IHG

4. Quality Inn & Conference Center Brattleboro North

5. Deerhill Inn

6. Econo Lodge Brattleboro South

7. Black Mountain Inn

8. Blue Gentian Lodge at Magic Mountain

9. Comfort Inn & Suites Brattleboro I-91

10. Dalem's Chalet

Top Windham County Hotel Reviews

Chalet 239

Inn At Mount Snow

The Putney Inn

Latchis Hotel

Hampton Inn Brattleboro

Black Mountain Inn

Econo Lodge Brattleboro South

Travelodge by Wyndham Brattleboro VT

Deerfield Valley Inn

Explore a world of travel with Expedia

Hotels with a Pool in Windham County from $93

Upfront pricing

Treat yourself

Be picky

Top Cities in Windham County

Brattleboro

Check availability on Windham County Hotels with a Pool

Our top choices for Windham County hotels with a pool

1. Colonial Motel

2. Hampton Inn Brattleboro

3. Holiday Inn Express Hotel & Suites Brattleboro by IHG

4. Quality Inn & Conference Center Brattleboro North

5. Deerhill Inn

6. Econo Lodge Brattleboro South

7. Black Mountain Inn

8. Blue Gentian Lodge at Magic Mountain

9. Comfort Inn & Suites Brattleboro I-91

10. Dalem's Chalet

Top Windham County Hotel Reviews

Chalet 239

Explore a world of travel with Expedia