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 11 - Oct 12
Tomorrow
Oct 12 - Oct 13
Next weekend
Oct 16 - Oct 18
In two weeks
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 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 hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.

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.
₩198,358
₩218,194 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 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.

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.
₩189,714
₩205,840 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 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.

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.
₩194,807
₩211,365 total
includes taxes & fees
Nov 12 - Nov 13
Hampton Inn & Suites Keene
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 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.

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.
₩159,491
₩173,048 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 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.
A hotel lobby with a reception desk, seating area, and a wall with framed pictures.

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.
₩148,273
₩163,101 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 spacious lobby with a stone wall, a reception desk, and a large window.
A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.
A lobby with wooden paneling, a fireplace, and two green armchairs.

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.
₩152,656
₩167,921 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 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 modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.

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.
₩253,376
₩274,913 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.
₩357,742
₩393,514 total
includes taxes & fees
Nov 1 - Nov 2
Inn on Putney Road
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.
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.
A hotel room with two beds, a nightstand, a lamp, and a chair.

9. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
  • Refresh poolside with a seasonal summer dip at this Vermont motel for adults only.
₩133,289
₩146,618 total
includes taxes & fees
Nov 10 - Nov 11
Econo Lodge Brattleboro South
A large, two-story house with a snow-covered driveway and surrounding trees.
A cozy room with a brick fireplace, floral wallpaper, and comfortable seating.
An outdoor dining area with tables and chairs, umbrellas, and a view of a forested landscape.
A modern bathroom with a glass-enclosed shower, a bathtub, a vanity with a sink, and a mirror.

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.
₩403,606
₩437,917 total
includes taxes & fees
Oct 18 - Oct 19
Chesterfield Inn
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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
"This was the perfect location and having modern amenities and snacks and breakfast was lovely."
Margaret 2-night trip
Posted 4 hours 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 5 hours ago
Best Western Plus Keene Hotel
The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"We chose the Colonial Hotel because it was closest to an event we were attending in a nearby town. We usually stay at name brand hotels that have franchised properties across the country and that we have experienced as predictably good places to stay. The Colonial Hotel was definitely the right choice. Their front desk staff was welcoming and the room was comfortable and clean. We arrive late in the evening and did something we seldom do -- had dinner at the restaurant on the property. The Grille had a nice menu, the waiter staff was personable and attentive, and we enjoyed our seafood and beef meals. Should we return to this beautiful area of Massachusetts, this would be where we would stay again."
Paul 1-night trip
Posted 7 hours ago
The Colonial Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"I was specially impressed by the employee who walked extra miles to provide the information I asked for and more to make my staying and continuing travel easy and accessible. Shema, I really thank you for your help. God bless you!"
Kwan 2-night trip
Posted 18 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"Nice property. Room was nice and clean and Robert at the front desk was great."
KEVIN 1-night trip
Posted 1 day ago
Hampton Inn Brattleboro
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 3 days ago
Colonial Motel
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 4 days ago
Comfort Inn & Suites Brattleboro I-91

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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