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

Find Hotels with a Pool in Winchester, NH from CA $153

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Check availability on Winchester Hotels with a Pool

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for Winchester hotels with a pool

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 modern bathroom with a glass-enclosed shower, a white toilet, and a towel rack with two towels.

1. 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.
CA $178
CA $193 total
includes taxes & fees
Oct 25 - Oct 26
Keene Elm City Hotel, an Ascend Collection Hotel
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 hotel with a covered entrance, a clear sky, and a tree in the foreground.
A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.

2. 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.
CA $189
CA $208 total
includes taxes & fees
Nov 22 - Nov 23
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 lobby with wooden paneling, a fireplace, and two green armchairs.
A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.
A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.

3. 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.
CA $154
CA $169 total
includes taxes & fees
Nov 15 - Nov 16
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 lobby with a reception desk, two sofas, a coffee station, and a dining area.

4. 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.
CA $154
CA $169 total
includes taxes & fees
Nov 22 - Nov 23
Comfort Inn & Suites Brattleboro I-91
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 modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

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.
CA $227
CA $246 total
includes taxes & fees
Nov 19 - Nov 20
Hampton Inn & Suites Keene
An indoor swimming pool with a tiled edge, surrounded by lounge chairs and a small table.
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.

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.
CA $198
CA $215 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Keene Hotel
A swimming pool with lounge chairs and a covered umbrella.
A cozy reading area with wooden chairs, a table with newspapers, and potted plants.
A hotel with a clock tower, a parking lot, and a well-maintained garden.
A hotel room with a bed, two bedside lamps, a nightstand, a chair, and a small table.

7. Black Mountain Inn

Black Mountain Inn
Brattleboro
  • Refreshing poolside retreat in Black Mountain with seasonal swimming and scenic garden views.
CA $178
CA $196 total
includes taxes & fees
Nov 24 - Nov 25
Black Mountain Inn
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 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.

8. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
  • Refresh poolside with a seasonal summer dip at this Vermont motel for adults only.
CA $139
CA $153 total
includes taxes & fees
Nov 22 - Nov 23
Econo Lodge Brattleboro South
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.
CA $237
CA $257 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Keene Downtown
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 dining area with a round wooden table, white chairs, and a green wall.
A bathroom with a sink, a potted plant, and a window with a view.

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.
CA $374
CA $411 total
includes taxes & fees
Nov 1 - Nov 2
Inn on Putney Road
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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"Breakfast Convenient location"
Kimberly 2-night trip
Posted 1 hour ago
Best Western Plus Keene Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The hotel was fairly new. Coffee was the only thing I felt needed changed."
Debbie 1-night trip
Posted 4 days ago
Hampton Inn Brattleboro
Colonial Motel

Colonial Motel

8/10 Good
"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."
Andrea 3-night trip
Posted 5 days ago
Colonial Motel
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

8/10 Good
"Was a good room for a one night stay on a road trip."
Thomas 1-night trip
Posted 6 days ago
Comfort Inn & Suites Brattleboro I-91
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 13 days ago
Hampton Inn & Suites Greenfield

Frequently asked questions

What are some accommodations 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 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 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 like Birch Point and Rhododendron State Park. During your stay, check out 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 into account the local weather in Winchester can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.

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