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

Winchester Hotel with Pool

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Check availability on Winchester Hotel with Pool

Tonight
23 Sept - 24 Sept
Tomorrow
24 Sept - 25 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Winchester hotels with a pool

An indoor swimming pool with a tiled edge, surrounded by lounge chairs and a small table.
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.

1. 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.
HK$1,169
HK$1,268 total
includes taxes & fees
24 Sept - 25 Sept
Best Western Plus Keene Hotel
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 reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.
A hotel room with a bed, a desk, a chair, a wooden door, and a window.

2. 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.
HK$1,098
HK$1,191 total
includes taxes & fees
24 Sept - 25 Sept
Keene Elm City Hotel, an Ascend Collection Hotel
An indoor swimming pool with a tiled deck, safety signs, and a few chairs.
A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.
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.

3. 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.
HK$1,080
HK$1,188 total
includes taxes & fees
29 Sept - 30 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 spacious lobby with a stone wall, a reception desk, and a large window.
A lobby with wooden paneling, a fireplace, and two green armchairs.

4. 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.
HK$1,072
HK$1,179 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn Brattleboro
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 gym with treadmills, elliptical machines, and stationary bikes.
A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.

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.
HK$1,254
HK$1,361 total
includes taxes & fees
30 Sept - 1 Oct
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 reception desk, seating area, and a modern ceiling light fixture.
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.

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.
HK$1,530
HK$1,682 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Hotel & Suites Brattleboro by IHG
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.
A sunroom with large windows, a dining area with a table and chairs, and a sofa.
A room with a dining table, chairs, a sofa, and a red carpet leading to a door.
A hotel room with two beds, a nightstand, a lamp, and a chair.

7. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
  • Refresh poolside with a seasonal summer dip at this Vermont motel for adults only.
HK$780
HK$858 total
includes taxes & fees
22 Oct - 23 Oct
Econo Lodge Brattleboro South
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 bathroom with a bathtub, toilet, and a shower curtain.
A cozy reading area with wooden chairs, a table with newspapers, and potted plants.

8. Black Mountain Inn

Black Mountain Inn
Brattleboro
  • Refreshing poolside retreat in Black Mountain with seasonal swimming and scenic garden views.
HK$1,191
HK$1,311 total
includes taxes & fees
27 Sept - 28 Sept
Black Mountain Inn
An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.
A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".
A modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.
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.
HK$1,706
HK$1,851 total
includes taxes & fees
30 Sept - 1 Oct
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.
HK$2,848
HK$3,133 total
includes taxes & fees
24 Sept - 25 Sept
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

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"Bed was very comfortable, shower clean and had good water pressure. Didn’t spend much time there. Checked in at 4:00am and they gave us late check out at noon."
Pamela 1-night trip
Posted 22 hours ago
Hampton Inn & Suites Greenfield
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Great! Clean, comfortable, friendly staff!"
Noelle 1-night trip
Posted 3 days ago
Best Western Plus Keene Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The breakfast room was great"
bonnie 1-night trip
Posted 4 days ago
Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Though it's not a luxury hotel, the staff is exceptionally nice & helpful. the property is clean, there are carts for moving luggage, the breakfast service is fine. It's quiet. the bathroom is spacious w.nice towels & toiletries. Parking is easy."
Robert 1-night trip
Posted 5 days ago
Comfort Inn & Suites Brattleboro I-91

Frequently asked questions

What are some accommodation options with pools in Winchester?
The Colonial Hotel: Features a sauna, an indoor pool and free self parking. Colonial Motel: 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 complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Gardner Inn: 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, 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 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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