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
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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 entrance with a modern design, featuring a prominent entrance canopy and stone pillars.
A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.
A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.

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.
S$196
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG
A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.
A spacious lobby with a stone wall, a reception desk, and a large window.
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.

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 Nov - 9 Nov
Hampton Inn Brattleboro
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A modern bathroom with a glass-enclosed shower, a white toilet, and a towel rack with two towels.
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.

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$165
includes taxes & fees
2 Nov - 3 Nov
Keene Elm City Hotel, an Ascend Collection Hotel
An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.
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.
A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.

4. 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$209
includes taxes & fees
10 Nov - 11 Nov
Hampton Inn & Suites Keene
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 lobby with a reception desk, two sofas, a coffee station, and a dining area.
A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.

5. 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$156
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Brattleboro I-91
An indoor swimming pool with a tiled edge, surrounded by lounge chairs and a small table.
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.
A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

6. 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$197
includes taxes & fees
1 Nov - 2 Nov
Best Western Plus Keene Hotel
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 room with a dining table, chairs, a sofa, and a red carpet leading to a door.

7. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
  • Refresh poolside with a seasonal summer dip at this Vermont motel for adults only.
S$140
includes taxes & fees
8 Nov - 9 Nov
Econo Lodge Brattleboro South
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.
A living room with a fireplace, a pool table, and comfortable seating.
A room with a chessboard, leather chairs, a large vase, and a bookshelf.
A bathroom with a sink, a potted plant, and a window with a view.

8. 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$376
includes taxes & fees
1 Nov - 2 Nov
Inn on Putney Road
An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.
A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.
A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".
A hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.

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$263
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 modern bathroom with a glass-enclosed shower, a bathtub, a vanity with a sink, and a mirror.
A cozy room with a brick fireplace, floral wallpaper, and comfortable seating.
A hotel room with a large bed, a fireplace, a dining table with chairs, and a view of the outdoors through a sliding door.

10. 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.
S$418
includes taxes & fees
25 Oct - 26 Oct
Chesterfield Inn
View all properties

Choose what matters most at hotels with a pool in Winchester

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Winchester Hotel Reviews

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Absolutely loved our stay here with our two golden doodles! We were in town for our daughter’s hockey game. We stay in chain hotels most weekends snd leave our dogs home . We made a little trip out of this 2 game series and The Colonial Hotel was the perfect little getaway."
Jill 1-night trip
Posted 2 hours ago
The Colonial Hotel
Colonial Motel

Colonial Motel

8/10 Good
"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."
Leonard 3-night trip
Posted 2 days ago
Colonial Motel
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"Staff was helpful and super friendly. Rooms were clean and looked recently renovated. Thank you for a great stay, highly recommended and will return."
Robert 2-night trip
Posted 2 days ago
Hampton Inn & Suites Greenfield
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"We had a one night stay recently. We were on the newly-renovated 4th floor, which was very nice. The room was very clean. We were there early, so we went to the 99 Restaurants bar that was right in front of the Comfort Inn. Check-in was easy and the staff were very pleasant. Room was very nice. We did have an issue with the television, but staff responded quickly and solved the issue. The free breakfast in the morning was very nice. Pancakes, waffles (with fruit toppings & syrup), bacon, breads, bagels and muffins, fresh fruit, cereals, yogurts. Many beverage options. A very nice selection! Staff was right there to replenish anything that was running low. Parking was plentiful, and right in front of the entrance. Check-out was fast and easy. I would highly recommend Comfort Inn & Suites!"
Lori 1-night trip
Posted 3 days ago
Comfort Inn & Suites Brattleboro I-91

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 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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