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

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Check availability on Winchester Hotels with a Pool

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.
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.

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.
₩198,875
₩218,762 total
includes taxes & fees
Nov 8 - Nov 9
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 gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

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.
₩188,941
₩205,001 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Keene Hotel
An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.
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.
A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.

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.
₩206,494
₩224,046 total
includes taxes & fees
Oct 25 - Oct 26
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 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.

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.
₩158,841
₩172,342 total
includes taxes & fees
Nov 2 - Nov 3
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.
₩147,669
₩162,436 total
includes taxes & fees
Nov 8 - Nov 9
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 lobby with wooden paneling, a fireplace, and two green armchairs.
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.
₩155,437
₩170,980 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Brattleboro
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 hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.
A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".

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.
₩252,344
₩273,793 total
includes taxes & fees
Oct 25 - Oct 26
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 living room with a fireplace, a pool table, and comfortable seating.
A room with a chessboard, leather chairs, a large vase, and a bookshelf.

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.
₩356,285
₩391,911 total
includes taxes & fees
Nov 3 - Nov 4
Inn on Putney Road
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 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.

9. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
  • Refresh poolside with a seasonal summer dip at this Vermont motel for adults only.
₩132,746
₩146,020 total
includes taxes & fees
Nov 12 - Nov 13
Econo Lodge Brattleboro South
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.

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.
₩401,962
₩436,133 total
includes taxes & fees
Oct 18 - Oct 19
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"It is a charming inn with very lovely staff & family attending the guests. I highly recommend staying here if you appreciate history & charm! The building was built in 1788 I believe they said. We stayed inPikes Suite and were comfortable and happy. Yes, the beautiful old floors creak, but it’s all part of the charm of this lovely still family owned hideaway! I hope to return again!"
Diane 1-night trip
Posted 12 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"Clean room. Breakfast good for quick bite and coffee was good"
JAMES 1-night trip
Posted 1 day ago
Hampton Inn Brattleboro
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 2 days ago
Hampton Inn & Suites Greenfield
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"The hotel needs some updating, and could be a little cleaner. Bathroom door looked like it had not been cleaned in a long time. The staff was friendly, and breakfast was good."
Teresa D 1-night trip
Posted 2 days ago
Best Western Plus Keene 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 5 days ago
Colonial Motel

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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