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

Search Hotels with Swimming Pool in Winchester

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Check availability on Winchester Hotels with Swimming Pool

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
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 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.

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.
₹14,049
₹15,454 total
includes taxes & fees
8 Nov - 9 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 hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.
A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

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.
₹13,437
₹14,579 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 hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.
A gym with treadmills, elliptical machines, and stationary bikes.

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.
₹15,370
₹16,677 total
includes taxes & fees
19 Nov - 20 Nov
Hampton Inn & Suites Keene
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 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.

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.
₹12,056
₹13,080 total
includes taxes & fees
25 Oct - 26 Oct
Keene Elm City Hotel, an Ascend Collection Hotel
An indoor swimming pool with a tiled deck, safety signs, and a few chairs.
A hotel lobby with a reception desk, seating area, and a wall with framed pictures.
A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.
A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.

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.
₹10,618
₹11,680 total
includes taxes & fees
15 Nov - 16 Nov
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 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.

6. 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.
₹10,489
₹11,538 total
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn Brattleboro
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 hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.

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.
₹17,946
₹19,471 total
includes taxes & fees
28 Oct - 29 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 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 dining area with a round wooden table, white chairs, and a green wall.

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.
₹25,338
₹27,871 total
includes taxes & fees
3 Nov - 4 Nov
Inn on Putney Road
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.
An outdoor dining area with tables and chairs, umbrellas, and a view of a forested landscape.
A hotel room with a large bed, a fireplace, a dining table with chairs, and a view of the outdoors through a sliding door.

9. 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.
₹28,586
₹31,016 total
includes taxes & fees
22 Oct - 23 Oct
Chesterfield Inn
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.
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.
A sunroom with large windows, a dining area with a table and chairs, and a sofa.

10. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
  • Refresh poolside with a seasonal summer dip at this Vermont motel for adults only.
₹9,440
₹10,384 total
includes taxes & fees
19 Nov - 20 Nov
Econo Lodge Brattleboro South
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

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 12 hours 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 1 day ago
Colonial Motel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Excellent place to stay"
Matthew 1-night trip
Posted 1 day ago
Best Western Plus Keene Hotel
The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"We love this hotel! We stay every year when we go to Wachusett Mountain"
Mollie 1-night trip
Posted 2 days ago
The Colonial Hotel
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 3 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 10 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 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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