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

Hotels with Swimming Pools in Winchester

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Check availability on Winchester Hotels with Swimming Pools

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Winchester hotels with a pool

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, two sofas, a coffee station, and a dining area.
A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.

1. 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.
S$165
includes taxes & fees
6 Sept - 7 Sept
Comfort Inn & Suites Brattleboro I-91
A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.
A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.
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.

2. 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.
S$158
includes taxes & fees
8 Sept - 9 Sept
Hampton Inn Brattleboro
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.
A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.
A modern bathroom with a glass-enclosed shower, a white toilet, and a towel rack with two towels.

3. 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.
S$185
includes taxes & fees
8 Sept - 9 Sept
Keene Elm City Hotel, an Ascend Collection Hotel
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.

4. 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.
S$205
includes taxes & fees
27 Aug - 28 Aug
Best Western Plus Keene Hotel
An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.
A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.
A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.
A gym with treadmills, elliptical machines, and stationary bikes.

5. 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.
S$208
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn & Suites Keene
A swimming pool with a clear blue water, surrounded by lounge chairs and a lifebuoy on the wall.
A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.
A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.
A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.

6. 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.
S$241
includes taxes & fees
6 Sept - 7 Sept
Holiday Inn Express Hotel & Suites Brattleboro by IHG
A swimming pool with lounge chairs and a covered umbrella.
A hotel room with a bed, two bedside lamps, a nightstand, a chair, and a small table.
A cozy reading area with wooden chairs, a table with newspapers, and potted plants.
A bathroom with a bathtub, toilet, and a shower curtain.

7. Black Mountain Inn

Black Mountain Inn
Brattleboro
  • Refreshing poolside retreat in Black Mountain with seasonal swimming and scenic garden views.
S$166
includes taxes & fees
31 Aug - 1 Sept
Black Mountain Inn
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.
A hotel room with two beds, a nightstand, a lamp, and a chair.
A hotel lobby with a red carpet, a reception desk, a sofa, and chairs.
A sunroom with large windows, a dining area with a table and chairs, and a sofa.

8. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
  • Refresh poolside with a seasonal summer dip at this Vermont motel for adults only.
S$131
includes taxes & fees
30 Aug - 31 Aug
Econo Lodge Brattleboro South
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 multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".
A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.

9. 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.
S$247
includes taxes & fees
2 Sept - 3 Sept
Courtyard by Marriott Keene Downtown
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 room with a chessboard, leather chairs, a large vase, and a bookshelf.
A dining area with a round wooden table, white chairs, and a green wall.

10. Inn on Putney Road

Inn on Putney Road
Brattleboro
  • Tranquil outdoor pool retreat complements this historic bed & breakfast with garden views and mountain adventures.
S$411
includes taxes & fees
30 Aug - 31 Aug
Inn on Putney Road
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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

8/10 Good
"Clean room breakfast was good"
Lori 1-night trip
Posted 3 hours ago
Best Western Plus Keene Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"It was good!"
Ingrid 4-night trip
Posted 16 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

8/10 Good
"Basic room. Felt a little dated. Breakfast was amazing."
Jessica 1-night trip
Posted 2 days ago
Hampton Inn & Suites Greenfield
Colonial Motel

Colonial Motel

8/10 Good
"X"
Steven 1-night trip
Posted 2 days ago
Colonial Motel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Staff were extremely friendly. The whole place was clean. Hit tub was really a whirlpool..movement but no bubbles. So nice and warm though. Great stay!!"
Deborah 2-night trip
Posted 5 days ago
Hampton Inn Brattleboro
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

8/10 Good
"Clean room, very nice front desk staff. Breakfast was good - nice variety and the coffee machine delivered great fresh coffee. It was worth paying the extra cost for this hotel vs the others in the area that seemed a bit sketchy."
David 1-night trip
Posted 10 days ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"The front desk staff were friendly and engaged, the room was clean. That’s all we needed."
Morgan 1-night trip
Posted 12 days ago
Comfort Inn & Suites Brattleboro I-91

Frequently asked questions

What are some accommodation options with pools in Winchester?
The Colonial Hotel: Provides a sauna, an indoor pool and free self parking. Keene Elm City Hotel, an Ascend Collection Hotel: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Best Western Plus Keene Hotel: Offers buffet, an indoor pool and free self parking. Colonial Motel: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Days Inn by Wyndham Keene NH: Features buffet, 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, Pisgah State Park and Cass Pond. 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 19°C, while the coldest months are January and February, with an average of -2°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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