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Hotels with Swimming Pools in Winchester

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Check availability on Winchester Hotels with Swimming Pools

Tonight
7 Sept - 8 Sept
Tomorrow
8 Sept - 9 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 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 grand hallway with a chandelier, a staircase, and a table with flowers.
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.
S$205
includes taxes & fees
8 Oct - 9 Oct
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 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.
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.
S$209
includes taxes & fees
27 Sept - 28 Sept
Residence Inn by Marriott Hartford Avon
A large indoor swimming pool with multiple seating areas and large windows.
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.
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.

3. 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.
S$190
includes taxes & fees
20 Sept - 21 Sept
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.

4. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
  • Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness centre.
S$284
includes taxes & fees
8 Sept - 9 Sept
Avon Old Farms Hotel
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A wooden deck with a swing chair and a bench overlooking a lake.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.
A tented area with lush greenery and a dining setup.

5. 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.
S$279
includes taxes & fees
22 Sept - 23 Sept
Interlaken Inn & Resort
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.

6. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
S$370
includes taxes & fees
8 Sept - 9 Sept
Simsbury 1820 House
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 white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.
A long wooden table with potted plants and candle holders in a modern interior setting.

7. The Litchfield Inn

The Litchfield Inn
Litchfield
S$412
includes taxes & fees
30 Sept - 1 Oct
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 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 Centre.
S$376
includes taxes & fees
16 Sept - 17 Sept
Simsbury Inn
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.

9. 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.
S$226
includes taxes & fees
10 Sept - 11 Sept
Hampton Inn & Suites Hartford/Farmington
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 reception area with a computer desk, chairs, and a carpeted floor.
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.
S$178
includes taxes & fees
4 Oct - 5 Oct
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

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"Great location."
Nancy 3-night trip
Posted 1 day ago
Hampton Inn & Suites Hartford/Farmington
The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"The Farmington Inn is charming, comfortable and quiet, with an excellent location and easy access to all that CT has to offer."
Rachael Gagner 7-night trip
Posted 2 days ago
The Farmington Inn & Suites
Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Clean, quiet, great restaurant and pub. Food was over the top delicious!"
Kathryn 1-night trip
Posted 4 days ago
Avon Old Farms Hotel
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Excellent experience all around!"
Allan 2-night trip
Posted 6 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Very nice and charming place to stay. We had a wonderful experience and our kids felt very welcomed and happy."
Angela 1-night trip
Posted 6 days 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. Extended Stay America Suites Hartford Farmington: Provides a seasonal outdoor pool, an indoor pool and a full-service spa. Homewood Suites by Hilton Hartford-Farmington: Features a snack bar/deli, a pool and daily. Sheraton Hartford Hotel at Bradley Airport: Offers a sauna, a seasonal outdoor pool and buffet. Delamar West Hartford: Features a snack bar/deli, an indoor pool and free valet parking.
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 Winchester Historical Society.
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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