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Find Hotels with a Pool in Winchester, CT

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Check availability on Winchester Hotels with a Pool

Tonight
8 Oct - 9 Oct
Tomorrow
9 Oct - 10 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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.
AED 551
AED 634 total
includes taxes & fees
1 Nov - 2 Nov
Blackberry River Inn
A swimming pool with clear water, surrounded by a fence and trees.
A long wooden table with potted plants and candle holders in a modern interior setting.
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.

2. The Litchfield Inn

The Litchfield Inn
Litchfield
AED 1,140
AED 1,311 total
includes taxes & fees
2 Nov - 3 Nov
The Litchfield Inn
A large, historic building with a covered porch and outdoor seating area.
A grand foyer with a patterned carpet, a wooden staircase, a chandelier, a mounted deer head, and a large clock.
A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.
A large, historic house with multiple chimneys, a covered porch, and lush greenery.

3. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
AED 643
AED 803 total
includes taxes & fees
2 Nov - 3 Nov
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 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.
A stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.

4. 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.
AED 528
AED 607 total
includes taxes & fees
1 Nov - 2 Nov
Residence Inn by Marriott Hartford Avon
A large indoor swimming pool with multiple seating areas and large windows.
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.
A modern breakfast area with a counter, seating, and a refrigerator.
A modern hotel building with multiple floors and a prominent "HOME 2 SUITES BY HILTON" sign.

5. 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.
AED 479
AED 551 total
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites by Hilton Bristol
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A white two-story house with a front door, windows, and a chimney.
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.

6. 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.
AED 1,065
AED 1,285 total
includes taxes & fees
1 Nov - 2 Nov
The Old Inn On The Green
A person in a blue swimsuit relaxing in a hot tub with a pool in the background.
A spacious, well-lit event space with a glass ceiling, white tables, and a chandelier.
A brick building with a covered patio, a fountain, and a staircase leading to a second floor.
A large, multi-story building surrounded by dense forest, with a parking lot and a small green structure nearby.

7. Simsbury Inn

Simsbury Inn
Simsbury Center
  • Serene indoor pool escape with loungers and après-ski amenities in Simsbury Center.
AED 1,062
AED 1,301 total
includes taxes & fees
12 Oct - 13 Oct
Simsbury Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a house and trees.
A conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.
A spacious lobby with a grand staircase, multiple seating areas, and a reception desk.
A spacious lobby with a grand staircase, multiple seating areas, and a central decorative table.

8. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
  • Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness center.
AED 708
AED 894 total
includes taxes & fees
19 Oct - 20 Oct
Avon Old Farms Hotel
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.
A spacious lobby with large windows, a central plant, and multiple hanging lights.
A modern lobby with a reception desk, seating area, and a large decorative light fixture.

9. 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.
AED 590
AED 679 total
includes taxes & fees
18 Oct - 19 Oct
DoubleTree by Hilton Hotel Bristol, Connecticut
An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.
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.
A hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.

10. 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.
AED 609
AED 700 total
includes taxes & fees
12 Oct - 13 Oct
Hampton Inn & Suites Hartford/Farmington
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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

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Everything was perfect—the room, the service, the restaurant, the spa; everything was perfect. An unforgettable experience."
Moshe 2-night trip
Posted 1 month ago
Mayflower Inn & Spa, Auberge Collection

Frequently asked questions

What are some hotels with pools in Winchester?
Enjoy a restful stay with fast internet, smart TV and the company of your pet.: Offers a snack bar/deli, an indoor pool, and buffet. Waterfront House & Guest House Available in Winchester, CT!: Features a seasonal outdoor pool, an indoor pool, and a full-service spa. The Farmington Inn & Suites: Offers a sauna, a seasonal outdoor pool, and buffet. Delamar West Hartford: Offers a snack bar/deli, an indoor pool, and free valet parking. Extended Stay America Suites Hartford Farmington: Provides 2 bars, an indoor pool, and daily.
What is there to see and do in Winchester?
Make a point to visit attractions like Highland Lake and Laurel Lanes. During your stay, check out 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 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 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.