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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 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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 bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
₩254,649
₩292,847 total
includes taxes & fees
Oct 13 - Oct 14
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
₩416,027
₩478,431 total
includes taxes & fees
Nov 2 - Nov 3
The Litchfield Inn
A person in a blue swimsuit relaxing in a hot tub with a pool in the background.
A brick building with a covered patio, a fountain, and a staircase leading to a second floor.
A spacious, well-lit event space with a glass ceiling, white tables, and a chandelier.
A large, multi-story building surrounded by dense forest, with a parking lot and a small green structure nearby.

3. Simsbury Inn

Simsbury Inn
Simsbury Center
  • Serene indoor pool escape with loungers and après-ski amenities in Simsbury Center.
₩387,335
₩474,720 total
includes taxes & fees
Oct 13 - Oct 14
Simsbury 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 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.
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.

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.
₩192,528
₩221,407 total
includes taxes & fees
Nov 1 - Nov 2
Residence Inn by Marriott Hartford Avon
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 hotel with a prominent sign, a covered entrance, and a landscaped driveway.
A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.

5. 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.
₩199,364
₩229,269 total
includes taxes & fees
Oct 30 - Oct 31
Hampton Inn & Suites Hartford/Farmington
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 modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.

6. 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.
₩218,704
₩251,510 total
includes taxes & fees
Oct 18 - Oct 19
DoubleTree by Hilton Hotel Bristol, Connecticut
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 large, historic house with multiple chimneys, a covered porch, and lush greenery.
A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.

7. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
₩234,795
₩293,133 total
includes taxes & fees
Nov 4 - Nov 5
Simsbury 1820 House
A swimming pool with lounge chairs and a red door.
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.
A modern lobby with a yellow sofa, marble table, and two armchairs.

8. 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.
₩226,705
₩260,711 total
includes taxes & fees
Oct 25 - Oct 26
Homewood Suites by Hilton Hartford-Farmington
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.
A modern hotel room with a bed, sofa, leather chair, and a small table.
A wooden deck with a swing chair and a bench overlooking a lake.

9. Interlaken Inn & Resort

Interlaken Inn & Resort
Lakeville
  • Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.
₩324,477
₩373,149 total
includes taxes & fees
Oct 26 - Oct 27
Interlaken Inn & Resort
A swimming pool with lounge chairs and umbrellas, surrounded by trees.
A modern house with a white exterior, two wooden doors, and a grey awning.
A large, two-story house with a wrap-around porch, a central entrance, and a flag.
A dining area with a round table, chairs, a fireplace, and a variety of plants.

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.
₩609,818
₩754,901 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

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

10/10 Excellent
"Nice place close to west Hartford. Staff was helpful."
Ronald 1-night trip
Posted 2 days ago
Homewood Suites by Hilton Hartford-Farmington
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 9 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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