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

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 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.
A grand hallway with a chandelier, a staircase, and a table with flowers.

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
NT$6,058
NT$6,967 total
includes taxes & fees
Oct 13 - Oct 14
Blackberry River Inn
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.
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.

2. 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.
NT$4,588
NT$5,276 total
includes taxes & fees
Nov 1 - Nov 2
Residence Inn by Marriott Hartford Avon
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 long wooden table with potted plants and candle holders in a modern interior setting.
A white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.

3. The Litchfield Inn

The Litchfield Inn
Litchfield
NT$9,707
NT$11,163 total
includes taxes & fees
Nov 9 - Nov 10
The Litchfield Inn
A swimming pool with lounge chairs and a red door.
A modern lobby with a yellow sofa, marble table, and two armchairs.
A hotel with multiple buildings, a parking lot, and a well-maintained lawn.
A hotel room with a bed, a sofa, a desk, a chair, a TV, and a lamp.

4. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
Farmington
  • Indoor pool oasis for fitness and family fun just 5 minutes from attractions.
NT$5,402
NT$6,213 total
includes taxes & fees
Oct 25 - Oct 26
Homewood Suites by Hilton Hartford-Farmington
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
A spacious lobby with large windows, a central plant, and multiple hanging lights.
A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.
A modern lobby with a reception desk, seating area, and a large decorative light fixture.

5. 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.
NT$5,002
NT$5,753 total
includes taxes & fees
Oct 18 - Oct 19
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.

6. 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.
NT$5,041
NT$5,797 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Hartford/Farmington
A person in a blue swimsuit relaxing in a hot tub with a pool in the background.
A stone fountain with water spouting from the top, surrounded by greenery and a brick building with windows 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.

7. Simsbury Inn

Simsbury Inn
Simsbury Center
  • Serene indoor pool escape with loungers and après-ski amenities in Simsbury Center.
NT$9,215
NT$11,294 total
includes taxes & fees
Oct 12 - Oct 13
Simsbury Inn
A large, historic building with a covered porch and outdoor seating area.
A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.
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.

8. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
NT$5,586
NT$6,974 total
includes taxes & fees
Nov 4 - Nov 5
Simsbury 1820 House
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.
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.

9. 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.
NT$4,164
NT$4,789 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites by Hilton Bristol
A swimming pool with lounge chairs and umbrellas, surrounded by trees.
A large, two-story house with a wrap-around porch, a central entrance, and a flag.
A spacious living room with a large sectional sofa, a round coffee table, and a chandelier. There are large windows with curtains, a fireplace, and a view of greenery outside.
A modern house with a white exterior, two wooden doors, and a grey awning.

10. Belden House & Mews

Belden House & Mews
Litchfield Historic District
  • Seasonal outdoor pool complemented by massages and spa treatments elevates relaxation at this mountain retreat.
NT$14,532
NT$17,990 total
includes taxes & fees
Nov 1 - Nov 2
Belden House & Mews
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

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"The motel was clean and the room we stayed in was clean and smelled good. The staff was awsome . I would recommend the Double Tree to anyone."
Carroll 3-night trip
Posted 5 hours ago
DoubleTree by Hilton Hotel Bristol, Connecticut
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

8/10 Good
"Convience"
Malcolm 1-night trip
Posted 11 hours ago
Sheraton Hartford Hotel at Bradley Airport
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent
"It was very helpful to have a restaurant/bar right next door. We were tired from traveling and wasn't much close by, so we were very relieved to have a decent place to eat. The breakfast was also delicious and fresh."
Elke 1-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Plainville
Interlaken Inn & Resort

Interlaken Inn & Resort

10/10 Excellent
"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."
Suzanne 5-night trip
Posted 7 days ago
Interlaken Inn & Resort
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?
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 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.

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