A snow-covered town with a river running through it, surrounded by mountains and trees.

Winchester Hotels with Swimming Pool

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Check availability on Winchester Hotels with Swimming Pools

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

Our top choices for Winchester hotels with a pool

A swimming pool with a clear blue water, surrounded by lounge chairs and a lifebuoy on the wall.
A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.
A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.

1. Holiday Inn Express Hotel & Suites Brattleboro by IHG

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.
RM567
RM624 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG
An indoor swimming pool with a tiled edge, surrounded by lounge chairs and a small table.
A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

2. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
  • Splash into luxury at this hotel's sparkling indoor pool, complete with plush sun loungers and serene atmosphere.
RM578
RM627 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Plus Keene Hotel
An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.
A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.
A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.
A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.

3. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
  • Splash into serenity at this inviting indoor pool hotel, where year-round swimming meets complete comfort and relaxation.
RM631
RM685 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn & Suites Keene
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.
A hotel room with a bed, a desk, a chair, a wooden door, and a window.
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

4. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
  • Splash into comfort at this indoor pool oasis offering year-round aquatic escape in Keene.
RM518
RM562 total
includes taxes & fees
25 Oct - 26 Oct
Keene Elm City Hotel, an Ascend Collection Hotel
A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.
A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.
A lobby with wooden paneling, a fireplace, and two green armchairs.
A spacious lobby with a stone wall, a reception desk, and a large window.

5. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
  • Immerse in rejuvenating waters at this mountain-adjacent hotel featuring a pristine indoor pool and relaxing hot tub sanctuary.
RM454
RM500 total
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn Brattleboro
An indoor swimming pool with a tiled deck, safety signs, and a few chairs.
A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.
A hotel lobby with a reception desk, seating area, and a wall with framed pictures.
A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.

6. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
  • Relaxing indoor pool retreat with comfortable loungers sets the perfect stage for your Vermont ski getaway.
RM452
RM497 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Brattleboro I-91
An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.
A modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.
A hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.
A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".

7. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
Keene
  • Dive into the year-round aquatic escape at this art deco hotel with a pristine indoor pool.
RM772
RM837 total
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Keene Downtown
A large, two-story house with a snow-covered driveway and surrounding trees.
A hotel room with a large bed, a fireplace, a dining table with chairs, and a view of the outdoors through a sliding door.
A modern bathroom with a glass-enclosed shower, a bathtub, a vanity with a sink, and a mirror.
An outdoor dining area with tables and chairs, umbrellas, and a view of a forested landscape.

8. Chesterfield Inn

Chesterfield Inn
West Chesterfield
  • Serene mountain escape with a refreshing pool for a summer splash or winter warm-up at this rustic inn.
RM1,229
RM1,334 total
includes taxes & fees
18 Oct - 19 Oct
Chesterfield Inn
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.
A bathroom with a sink, a potted plant, and a window with a view.
A dining area with a round wooden table, white chairs, and a green wall.
A living room with a fireplace, a pool table, and comfortable seating.

9. Inn on Putney Road

Inn on Putney Road
Brattleboro
  • Tranquil outdoor pool retreat complements this historic bed & breakfast with garden views and mountain adventures.
RM1,089
RM1,198 total
includes taxes & fees
3 Nov - 4 Nov
Inn on Putney Road
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.
A hotel lobby with a red carpet, a reception desk, a sofa, and chairs.
A hotel room with two beds, a nightstand, a lamp, and a chair.
A room with a dining table, chairs, a sofa, and a red carpet leading to a door.

10. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
  • Refresh poolside with a seasonal summer dip at this Vermont motel for adults only.
RM406
RM447 total
includes taxes & fees
16 Nov - 17 Nov
Econo Lodge Brattleboro South
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Choose what matters most at hotels with a pool in Winchester

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Winchester Hotel Reviews

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"nice pool"
Dawn 1-night trip
Posted 4 hours ago
Best Western Plus Keene Hotel
Colonial Motel

Colonial Motel

10/10 Excellent
"Value for money. Clean and conveniently located. Friendly staff."
Swaraj 2-night trip
Posted 1 day ago
Colonial Motel
The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"."
michael 1-night trip
Posted 2 days ago
The Colonial Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"Clean room. Breakfast good for quick bite and coffee was good"
JAMES 1-night trip
Posted 5 days ago
Hampton Inn Brattleboro
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"This was the perfect location and having modern amenities and snacks and breakfast was lovely."
Margaret 2-night trip
Posted 6 days ago
Hampton Inn & Suites Greenfield

Frequently asked questions

What are some accommodation options with pools in Winchester?
Colonial Motel: Offers a sauna, an indoor pool and free self parking. The Colonial Hotel: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Latchis Hotel: Features buffet, an indoor pool and free self parking. Keene Elm City Hotel, an Ascend Collection Hotel: Provides buffet, an indoor pool and free self parking. Gardner Inn: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking.
What is there to see and do in Winchester?
Make a point to visit attractions such as Birch Point and Rhododendron State Park. During your stay, visit sights such as Winchester Speedpark, New England Sweetwater Farm & Distillery and Pisgah State Park. Take in the natural beauty of Winchester with the lakeside setting.
When is the best time to book a hotel with a pool in Winchester?
Taking the local weather in Winchester 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 19Β°C, while the coldest months are January and February, with an average of -2Β°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.

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