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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
Sep 10 - Sep 11
Tomorrow
Sep 11 - Sep 12
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

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 bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.
A grand hallway with a chandelier, a staircase, and a table with flowers.
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.
CA $203
CA $233 total
includes taxes & fees
Sep 21 - Sep 22
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 hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.
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.

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.
CA $198
CA $228 total
includes taxes & fees
Sep 27 - Sep 28
Residence Inn by Marriott Hartford Avon
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 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.

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.
CA $180
CA $207 total
includes taxes & fees
Sep 20 - Sep 21
Home2 Suites by Hilton Bristol
A large, historic building with a covered porch and outdoor seating area.
A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a 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.

4. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
CA $248
CA $309 total
includes taxes & fees
Sep 28 - Sep 29
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 reception desk.
A spacious indoor dining area with high ceilings, large windows, and a brick wall.
A spacious lobby with a grand staircase, multiple seating areas, and a central decorative table.

5. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
  • Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness centre.
CA $266
CA $336 total
includes taxes & fees
Sep 15 - Sep 16
Avon Old Farms Hotel
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 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.

6. The Litchfield Inn

The Litchfield Inn
Litchfield
CA $390
CA $449 total
includes taxes & fees
Sep 30 - Oct 1
The Litchfield Inn
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 stone fountain with water spouting from the top, surrounded by greenery and a brick building with windows in the background.
A brick building with a covered patio, a fountain, and a staircase leading to a second floor.

7. Simsbury Inn

Simsbury Inn
Simsbury Center
  • Serene indoor pool escape with loungers and après-ski amenities in Simsbury Centre.
CA $329
CA $409 total
includes taxes & fees
Sep 16 - Sep 17
Simsbury 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 wooden deck with a swing chair and a bench overlooking a lake.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

8. 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.
CA $264
CA $303 total
includes taxes & fees
Sep 22 - Sep 23
Interlaken Inn & Resort
A backyard with a swimming pool, surrounded by lush greenery and a wooden deck.
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.
A dining area with wooden tables and chairs, large windows with white frames, and wall-mounted light fixtures.

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.
CA $292
CA $335 total
includes taxes & fees
Sep 14 - Sep 15
Cornwall Inn and Lodge
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.
A spacious lobby with large windows, a central plant, and multiple hanging lights.
A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.

10. 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.
CA $209
CA $241 total
includes taxes & fees
Sep 20 - Sep 21
DoubleTree by Hilton Hotel Bristol, Connecticut
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

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"It’s handy to the air port and when ever we fly we stay at the hotel"
Sandy 1-night trip
Posted 1 hour ago
Sheraton Hartford Hotel at Bradley Airport
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"Room was clean and had a pleasant, light flowery scent. Refrigerator was making a loud noise and then stopped working. I notified the front desk in the morning and a new refrigerator was installed by the time I returned later that day. I think they installed it immediately. The fitness center was nice. It was closed the second day of my stay so new equipment could be installed. They were missing lighter weights. I would have liked to use some. I didn’t swim in the pool or use the hot tub but both looked clean and inviting. Breakfast had something for everyone. I would stay here again."
Stacey Robyn 3-night trip
Posted 5 hours ago
Hampton Inn & Suites Hartford/Farmington
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

8/10 Good
"There was a slight odor. Maybe you could provide air freshener in some outlets. The rooms are beautiful. I would recommend to friends."
Norma 7-night trip
Posted 17 hours ago
Homewood Suites by Hilton Hartford-Farmington
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 7 days ago
Avon Old Farms Hotel
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 9 days ago
Mayflower Inn & Spa, Auberge Collection

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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