Default HTG hotel image

Hotels with Swimming Pool in Winchester, Winsted

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with Swimming Pool

Tonight
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

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 bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.
A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
P11,752
P13,515 total
includes taxes & fees
Aug 30 - Aug 31
Blackberry River Inn
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.
A spacious room with a high ceiling, a ceiling fan, a large window with a view of greenery, a white sofa, a black leather chair, and a wooden table with a computer setup.
A modern bathroom with a walk-in shower, a toilet, a sink, and a bathtub.
A modern living room with a sofa, ottoman, and green armchair, a coffee table with a vase of flowers, and a wooden cabinet with decorative items.

2. Sunny Peace Homestay

Sunny Peace Homestay
Harwinton
P8,072
P12,839 total
includes taxes & fees
Aug 31 - Sep 1
Sunny Peace Homestay
A large, historic building with a covered porch and outdoor seating area.
A large, historic house with multiple chimneys, a covered porch, and lush greenery.
A sign for the Simsbury House, indicating it is a historic building from 1820.
A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.

3. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
P10,453
P13,088 total
includes taxes & fees
Aug 30 - Aug 31
Simsbury 1820 House
A large indoor swimming pool with multiple seating areas and large windows.
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.
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.

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.
P8,188
P9,416 total
includes taxes & fees
Sep 6 - Sep 7
Home2 Suites by Hilton Bristol
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 lobby with a grand staircase, multiple seating areas, and a reception desk.

5. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
  • Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness center.
P9,442
P12,210 total
includes taxes & fees
Sep 3 - Sep 4
Avon Old Farms Hotel
A swimming pool with lounge chairs and a covered seating area, surrounded by multi-story buildings with visible windows and a brick facade.
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.
A stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.
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.
P9,408
P10,819 total
includes taxes & fees
Sep 20 - Sep 21
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 spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.
An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.

7. 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.
P8,628
P9,923 total
includes taxes & fees
Sep 7 - Sep 8
Hampton Inn & Suites Hartford/Farmington
A person in a blue swimsuit relaxing in a hot tub with a pool in the background.
A sign for The Simsbury Inn, featuring a swan on water.
A large, multi-story building surrounded by dense forest, with a parking lot and a small green structure nearby.
A spacious, well-lit event space with a glass ceiling, white tables, and a chandelier.

8. Simsbury Inn

Simsbury Inn
Simsbury Center
  • Serene indoor pool escape with loungers and après-ski amenities in Simsbury Center.
P14,881
P18,473 total
includes taxes & fees
Sep 16 - Sep 17
Simsbury Inn
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 rustic bedroom with a large bed, wooden headboard, and a wooden floor. There is a chair and a small table with a lamp.

9. The Litchfield Inn

The Litchfield Inn
Litchfield
P19,306
P22,202 total
includes taxes & fees
Aug 30 - Aug 31
The Litchfield Inn
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A tented area with lush greenery and a dining setup.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.
A wooden deck with a swing chair and a bench overlooking a lake.

10. 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.
P13,305
P15,301 total
includes taxes & fees
Sep 22 - Sep 23
Interlaken Inn & Resort
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
"nons"
Melanie Anne 2-night trip
Posted 4 hours ago
Homewood Suites by Hilton Hartford-Farmington
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"The staff was super helpful and the facilities were c clean and modern. Breakfast was fresh and had good choices."
Lauren 1-night trip
Posted 7 hours ago
Hampton Inn & Suites Hartford/Farmington
The Farmington Inn & Suites

The Farmington Inn & Suites

8/10 Good
"The staff were friendly and helpful, but you have to pay 17.25 a day (even the day you check out) for amenities that we never used. The back door we used looks all scratched up and worn metal door on the bottom. Bad 1st impression. Rooms are prettily decorated with wall paper and curtains that match. 4 poster beds looked great and were comfortable. Breakfast was good with enough choices. English tea bags weren't replenished after one day and don't think they have a designated person to handle only the food area. We left early every day and came back late. It was quiet and clean so recommend it, but be aware you pay for amenities whether you use them or not. Staff were helpful and friendly."
Cynthia 3-night trip
Posted 4 days ago
The Farmington Inn & Suites
Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Good"
Jeremy J 3-night trip
Posted 5 days ago
Avon Old Farms Hotel
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Beautiful property with lovely pool and spa area. The rooms are beautifully decorated. The staff are all friendly, welcoming, and very helpful. The grounds and gardens are well maintained. The hiking trail is highly recommended. My room in the main house was a bit noisy; the room above mine appeared to be a utility room that was active early in the morning. I could hear footsteps throughout the day. The dinner was overrated, but the breakfast and lunch were delicious."
Mary 3-night trip
Posted 8 days ago
Mayflower Inn & Spa, Auberge Collection
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

10/10 Excellent
"All the staff members I met were cheerful & helpful. I asked for a ground floor room, upon arrival, got a very nice one at no extra charge. I was in the area for a music festival, plan on booking a stay again , next year."
Peter 2-night trip
Posted 12 days ago
Americas Best Value Inn Torrington CT

Frequently asked questions

What are some hotels with pools in Winchester?
Sheraton Hartford Hotel at Bradley Airport: Features a snack bar/deli, an indoor pool, and buffet. Homewood Suites by Hilton Hartford-Farmington: Features a sauna, a seasonal outdoor pool, and buffet. The Farmington Inn & Suites: Provides a seasonal outdoor pool, an indoor pool, and a full-service spa. Avon Old Farms Hotel: Features a snack bar/deli, a pool, and daily. Delamar West Hartford: Offers daily, an indoor pool, and complimentary wired internet access.
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 Burr Pond State Park, The Marina at Highland Lake, and Platt Hill State Park.
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.

Explore a world of travel with Expedia