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Check availability on Windham Hotels with Pool

Tonight
13 Sep - 14 Sep
Tomorrow
14 Sep - 15 Sep
Next weekend
18 Sep - 20 Sep
In two weeks
25 Sep - 27 Sep

Our top choices for Windham hotels with a pool

A swimming pool with a wooden deck and a red building in the background.
A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.
A Christmas tree decorated with lights, ornaments, and a bow.
A bar area with a sign reading "MAGIC" and "featured Vermont beers".

1. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
  • Slope-side sanctuary beckons with mountain vistas and a seasonal outdoor pool.
2.373.235 ₫
2.717.355 ₫ total
includes taxes & fees
14 Sept - 15 Sept
The Upper Pass Lodge at Magic Mountain
A modern house with a pool, surrounded by lush greenery and mountains in the background.
A sunroom with a round table covered by a plaid tablecloth, surrounded by chairs, large windows offering a view of a garden and pond.
A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.
A hot tub on a covered porch with a view of autumn foliage.

2. Blue Gentian Lodge at Magic Mountain

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.
3.862.080 ₫
4.248.289 ₫ total
includes taxes & fees
14 Sept - 15 Sept
Blue Gentian Lodge at Magic Mountain
A swimming pool with a brick border and metal handrails.
A large, white, two-story house with a steeply pitched roof, a balcony, and a staircase leading to the upper floor.
A room with a stone fireplace, large windows with curtains, a patterned rug, and a plush chair.
A kitchen with wooden cabinets, a built-in stove, a microwave, and a sink.

3. Windham Hill Inn

Windham Hill Inn
West Townshend
  • Serene seasonal outdoor pool offers 24-hour summer swimming amid Vermont's lush Windham Hills.
6.193.584 ₫
6.751.006 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Windham Hill Inn
A rectangular swimming pool with a metal ladder, surrounded by a white fence, and shaded by trees.
A spacious room with high ceilings, wooden beams, large windows, and tables and chairs arranged for dining.
An aerial view of a residential area with houses, a tennis court, and a swimming pool.
A large two-story house with a front porch and a well-maintained lawn.

4. The Landgrove

The Landgrove
Londonderry
4.696.347 ₫
5.119.018 ₫ total
includes taxes & fees
20 Sept - 21 Sept
The Landgrove
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.
A bar area with wooden ceiling beams, bar stools, and a long counter with bottles and glasses.
A group of people at a bar with wooden walls and hanging pendant lights.
A snow-covered town with a church featuring a clock tower, surrounded by buildings and a mountain in the background.

5. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
Stratton
  • Alpine resort's outdoor pool offers sun-kissed mountain views with poolside loungers and hot tub relaxation.
9.201.600 ₫
11.437.589 ₫ total
includes taxes & fees
14 Sept - 15 Sept
Long Trail House at Stratton Mountain Resort
An indoor swimming pool with four chairs and a hot tub.
A spacious lobby with a fireplace, leather seating, and a chandelier.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.
A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

6. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
  • Dive into alpine luxury with this heated indoor pool and hot tub sanctuary, steps away from Okemo Mountain's world-class skiing.
4.164.048 ₫
4.747.014 ₫ total
includes taxes & fees
14 Sept - 15 Sept
Pointe at Castle Hill Resort
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Choose what matters most at hotels with a pool in Windham

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Windham Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"We had a fantastic stay from start to finish. The staff was incredibly welcoming, attentive, and helpful throughout our entire visit, making us feel right at home. The accommodations were wonderful, and most importantly, our kid had an absolute blast! Everything went smoothly, and we couldn't have asked for a better experience for our family. Highly recommended!"
Min 1-night trip
Posted 1 hour ago
Jackson Gore Village, A Vail Resorts Property
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent
"Great property but a needs a little more tender care."
Sylvia 2-night trip
Posted 7 hours ago
The Equinox Golf Resort And Spa
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Room was clean and comfortable, there was water and cookies available at check in, the coffee bar was well stocked and had a variety, the hotel was tucked away in a quiet area, there was a row of electric car chargers and the breakfast had a good variety. We would stay here, again!"
Amy 1-night trip
Posted 19 hours ago
Comfort Inn & Suites Brattleboro I-91
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

8/10 Good
"Good location and good restaurant on the property. We enjoyed daily happy hour on the front porch sitting in the rocking chairs."
Oksana 2-night trip
Posted 23 hours ago
Kimpton Taconic Hotel by IHG
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Great place for overnight stay"
Francesca 1-night trip
Posted 1 day ago
Hampton Inn Brattleboro
The Manchester View

The Manchester View

10/10 Excellent
"Great place. Friendly, clean and serene. The breakfast was a cut above the typical continental fare and it was awesome to use the hot tub before driving into town for dinner. The only one thing that was tricky was the shower -- it's not well-designed so it's hard to stop water from spraying on to the floor. Other than that, no complaints!"
Alison 1-night trip
Posted 1 day ago
The Manchester View

Frequently asked questions

What is there to see and do in Windham?
Make a point to visit attractions such as Stoughton Pond Recreation Area and Lowell Lake State Park. Discover sights such as Magic Mountain Ski Resort, Jamaica State Park and Viking Nordic Center during your stay.
When is the best time to book a hotel with a pool in Windham?
Taking the local weather in Windham into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windham are January, March, November and February, with each month seeing an average of 35 cm of snowfall.