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Check availability on Winchester Hotels with Pool

Tonight
23 Aug - 24 Aug
Tomorrow
24 Aug - 25 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept

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.
Rp3.361.860
Rp3.866.139 total
includes taxes & fees
24 Aug - 25 Aug
Blackberry River 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.

2. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
Rp2.990.286
Rp3.744.050 total
includes taxes & fees
24 Aug - 25 Aug
Simsbury 1820 House
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.
Rp2.700.989
Rp3.492.796 total
includes taxes & fees
24 Aug - 25 Aug
Avon Old Farms Hotel
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.
A house with a garden featuring purple flowers and a stone wall.
A modern bathroom with a walk-in shower, a toilet, a sink, and a bathtub.
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.

4. Sunny Peace Homestay

Sunny Peace Homestay
Harwinton
Rp2.309.067
Rp3.672.832 total
includes taxes & fees
25 Aug - 26 Aug
Sunny Peace Homestay
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 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.

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.
Rp2.306.944
Rp2.652.986 total
includes taxes & fees
30 Aug - 31 Aug
Home2 Suites by Hilton Bristol
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.
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.
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.
Rp2.691.257
Rp3.094.945 total
includes taxes & fees
13 Sept - 14 Sept
Residence Inn by Marriott Hartford Avon
A swimming pool with clear water, surrounded by a fence and trees.
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.
A lobby with a chandelier, a reception desk, and a sign indicating an exit.

7. The Litchfield Inn

The Litchfield Inn
Litchfield
Rp4.832.038
Rp5.556.844 total
includes taxes & fees
24 Aug - 25 Aug
The Litchfield Inn
An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.
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.
An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.

8. 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.
Rp2.452.035
Rp2.819.841 total
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Hartford/Farmington
A backyard with a swimming pool, surrounded by lush greenery and a wooden deck.
A dining area with wooden tables and chairs, large windows with white frames, and wall-mounted light fixtures.
A covered patio with a wooden table and chairs, a sofa, and a ceiling fan.
A hotel room with a large bed, two bedside lamps, a chair, a small table, and a rug.

9. Cornwall Inn and Lodge

Cornwall Inn and Lodge
Cornwall Bridge
  • Serene seasonal outdoor pool retreat nestled near Mohawk Mountain, where pool loungers and umbrellas invite summer relaxation.
Rp3.744.050
Rp4.305.658 total
includes taxes & fees
24 Aug - 25 Aug
Cornwall Inn and Lodge
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 Fairfield Inn & Suites hotel with a large parking lot and snow-covered ground.

10. 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.
Rp2.008.623
Rp2.309.917 total
includes taxes & fees
6 Sept - 7 Sept
Fairfield Inn & Suites by Marriott Plainville
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

The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"Breakfast until 11am was very helpful"
Svetlana 1-night trip
Posted 11 hours ago
The Farmington Inn & Suites
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"We have stayed here many times. We always stay here the day before we fly and then the night that we come home. The rooms are always comfortable and clean . The front desk staff are always very nice. It’s an easy walk across the hallway from the airport itself. We have eaten in the restaurant quite a few times and our food is always excellent. I highly recommend staying here."
Linda 1-night trip
Posted 1 day ago
Sheraton Hartford Hotel at Bradley Airport
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 1 day 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 6 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 high-speed (wired) Internet access.
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 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 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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