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Check availability on Winchester Hotels with a Pool

Tonight
Sep 3 - Sep 4
Tomorrow
Sep 4 - Sep 5
This weekend
Sep 4 - Sep 6
Next weekend
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 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.
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.
￥22,150
￥25,472 total
includes taxes & fees
Oct 4 - Oct 5
Blackberry River Inn
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.
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.
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
￥20,721
￥32,959 total
includes taxes & fees
Sep 17 - Sep 18
Sunny Peace Homestay
A large indoor swimming pool with multiple seating areas and large windows.
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.
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.

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.
￥20,888
￥24,021 total
includes taxes & fees
Sep 20 - Sep 21
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.
A hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.
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.
￥22,809
￥26,231 total
includes taxes & fees
Sep 13 - Sep 14
Residence Inn by Marriott Hartford Avon
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
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.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

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.
￥30,359
￥34,913 total
includes taxes & fees
Sep 22 - Sep 23
Interlaken Inn & Resort
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 reception desk.
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.

6. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
  • Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness center.
￥27,954
￥35,617 total
includes taxes & fees
Sep 7 - Sep 8
Avon Old Farms Hotel
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 hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.
A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.

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.
￥21,881
￥25,164 total
includes taxes & fees
Sep 10 - Sep 11
Hampton Inn & Suites Hartford/Farmington
A person in a blue swimsuit relaxing in a hot tub with a pool in the background.
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.
A brick building with a covered patio, a fountain, and a staircase leading to a second floor.

8. Simsbury Inn

Simsbury Inn
Simsbury Center
  • Serene indoor pool escape with loungers and après-ski amenities in Simsbury Center.
￥38,290
￥47,535 total
includes taxes & fees
Sep 16 - Sep 17
Simsbury Inn
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 white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.

9. The Litchfield Inn

The Litchfield Inn
Litchfield
￥45,272
￥52,063 total
includes taxes & fees
Sep 30 - Oct 1
The Litchfield 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 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.

10. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
￥36,042
￥44,187 total
includes taxes & fees
Sep 10 - Sep 11
Simsbury 1820 House
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

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Great place"
Salvador 1-night trip
Posted 7 hours 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 2 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 2 days ago
Mayflower Inn & Spa, Auberge Collection
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

10/10 Excellent
"nons"
Melanie Anne 2-night trip
Posted 6 days ago
Homewood Suites by Hilton Hartford-Farmington

Frequently asked questions

What are some hotels with pools in Winchester?
Waterfront House & Guest House Available in Winchester, CT!: Offers a snack bar/deli, an indoor pool, and buffet. The Farmington Inn & Suites: Provides a seasonal outdoor pool, an indoor pool, and a full-service spa. Extended Stay America Suites Hartford Farmington: Features a snack bar/deli, a pool, and daily. Homewood Suites by Hilton Hartford-Farmington: Offers a sauna, a seasonal outdoor pool, and buffet. Sheraton Hartford Hotel at Bradley Airport: 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 like Highland Lake and Laurel Lanes. During your stay, check out 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 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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