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Hotels with Swimming Pools in Winchester

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Check availability on Winchester Hotels with Swimming Pools

Tonight
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Winchester hotels with a pool

An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.
A grand hallway with a chandelier, a staircase, and a table with flowers.
A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
S$254
includes taxes & fees
25 Oct - 26 Oct
Blackberry River Inn
An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.
A hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.
A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.
An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.

2. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
Farmington
  • Swim and unwind at this stylish retreat where guests adore the indoor pool and hot tub for year-round aquatic relaxation.
S$211
includes taxes & fees
20 Nov - 21 Nov
Hampton Inn & Suites Hartford/Farmington
A swimming pool with lounge chairs and umbrellas, surrounded by a house and trees.
A spacious lobby with a grand staircase, multiple seating areas, and a central decorative table.
A conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.
A spacious indoor dining area with high ceilings, large windows, and a brick wall.

3. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
  • Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness centre.
S$287
includes taxes & fees
1 Nov - 2 Nov
Avon Old Farms Hotel
A large indoor swimming pool with multiple seating areas and large windows.
A modern hotel building with multiple floors and a prominent "HOME 2 SUITES BY HILTON" sign.
A modern lounge with a pool table, comfortable seating, and a large window offering a view of the outdoors.
A modern breakfast area with a counter, seating, and a refrigerator.

4. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
Bristol
  • Serene hotel with an indoor pool escape just steps away from relaxing in a soothing hot tub.
S$192
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites by Hilton Bristol
A large, historic building with a covered porch and outdoor seating area.
A sign for the Simsbury House, indicating it is a historic building from 1820.
A grand foyer with a patterned carpet, a wooden staircase, a chandelier, a mounted deer head, and a large clock.
A large, historic house with multiple chimneys, a covered porch, and lush greenery.

5. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
S$289
includes taxes & fees
25 Oct - 26 Oct
Simsbury 1820 House
A swimming pool with lounge chairs and a covered seating area, surrounded by multi-story buildings with visible windows and a brick facade.
A stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.
A hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.
A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.

6. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
Avon
  • Splash into mountain adventures with a rejuvenating seasonal outdoor pool and hot tub retreat just steps from scenic trails.
S$199
includes taxes & fees
19 Nov - 20 Nov
Residence Inn by Marriott Hartford Avon
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
A modern lobby with a reception desk, seating area, and a large decorative light fixture.
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.
A spacious lobby with large windows, a central plant, and multiple hanging lights.

7. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
Bristol
  • Serene indoor saltwater pool retreat creates an oasis of relaxation with a nearby hot tub in this upscale Connecticut hotel.
S$216
includes taxes & fees
8 Nov - 9 Nov
DoubleTree by Hilton Hotel Bristol, Connecticut
A swimming pool with clear water, surrounded by a fence and trees.
A lobby with a chandelier, a reception desk, and a sign indicating an exit.
A rustic bedroom with a large bed, wooden headboard, and a wooden floor. There is a chair and a small table with a lamp.
A long wooden table with potted plants and candle holders in a modern interior setting.

8. The Litchfield Inn

The Litchfield Inn
Litchfield
S$424
includes taxes & fees
15 Nov - 16 Nov
The Litchfield Inn
An indoor swimming pool with a 'No Diving' sign, a glass enclosure, and a tiled wall with a 'No Diving' sign.
A lobby with a blue sofa, a small round table, and a fireplace.
A hotel room with a sofa, two small tables, a TV, a desk, and a mirror.
A hotel reception area with a computer desk, chairs, and a carpeted floor.

9. Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
Plainville
  • Swim year-round at this hotel's indoor pool, with 24-hour fitness centre just steps away.
S$149
includes taxes & fees
8 Nov - 9 Nov
Fairfield Inn & Suites by Marriott Plainville
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

10. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
  • Dive into summer luxury at this historic inn's outdoor pool surrounded by garden serenity and natural wonders.
S$447
includes taxes & fees
14 Nov - 15 Nov
The Old Inn On The Green
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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

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Hotel was clean and modern. Hotel bar was fun and front desk was quick, friendly and efficient."
Jennifer 1-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent
"Very nice, comfortable stay. Would stay there again."
Erin 1-night trip
Posted 8 days ago
Fairfield Inn & Suites by Marriott Plainville
Simsbury Inn

Simsbury Inn

8/10 Good
"The rooms are nice and very comfortable. The ground are beautiful. The breakfast buffet was often cold and the food not great."
Cynthia 4-night trip
Posted 11 days ago
Simsbury Inn

Frequently asked questions

What are some hotels with pools in Winchester?
The Farmington Inn & Suites: Offers a snack bar/deli, an indoor pool and buffet. Delamar West Hartford: Features a seasonal outdoor pool, an indoor pool and a full-service spa. Extended Stay America Suites Hartford Farmington: Offers a sauna, a seasonal outdoor pool and buffet. Homewood Suites by Hilton Hartford-Farmington: Offers a snack bar/deli, an indoor pool and free valet parking. Sheraton Hartford Hotel at Bradley Airport: Provides 2 bars, an indoor pool and daily.
What is there to see and do in Winchester?
Make a point to visit attractions such as Highland Lake and Laurel Lanes. During your stay, visit sights such as The Marina at Highland Lake, Burr Pond State Park and Winchester Historical Society.
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 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 15 cm of snowfall.

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