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Find Hotels with a Pool in Winchester, CT from CA $169

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Check availability on Winchester Hotels with a Pool

Tonight
Oct 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 $243
CA $280 total
includes taxes & fees
Oct 26 - Oct 27
Blackberry River Inn
An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.
An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.
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.

2. 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.
CA $202
CA $232 total
includes taxes & fees
Oct 30 - Oct 31
Hampton Inn & Suites Hartford/Farmington
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.

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 $183
CA $211 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites by Hilton Bristol
An indoor swimming pool with a 'No Diving' sign, a glass enclosure, and a tiled wall with a 'No Diving' sign.
A hotel reception area with a computer desk, chairs, and a carpeted floor.
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.

4. 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.
CA $147
CA $169 total
includes taxes & fees
Nov 8 - Nov 9
Fairfield Inn & Suites by Marriott Plainville
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.

5. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
CA $252
CA $314 total
includes taxes & fees
Nov 1 - Nov 2
Simsbury 1820 House
A swimming pool with lounge chairs and umbrellas, surrounded by a house and trees.
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.
A spacious lobby with a grand staircase, multiple seating areas, and a reception desk.

6. 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 $240
CA $307 total
includes taxes & fees
Nov 6 - Nov 7
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.
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.
A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.

7. 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 $190
CA $219 total
includes taxes & fees
Nov 19 - Nov 20
Residence Inn by Marriott Hartford Avon
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
A spacious lobby with large windows, a central plant, and multiple hanging lights.
A modern lobby with a reception desk, seating area, and a large decorative light fixture.
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

8. 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 $206
CA $237 total
includes taxes & fees
Nov 8 - Nov 9
DoubleTree by Hilton Hotel Bristol, Connecticut
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.

9. The Litchfield Inn

The Litchfield Inn
Litchfield
CA $417
CA $480 total
includes taxes & fees
Nov 8 - Nov 9
The Litchfield Inn
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
A white two-story house with a front door, windows, and a chimney.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

10. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
  • Dive into summer luxury at this historic inn's outdoor pool surrounded by garden serenity and natural wonders.
CA $408
CA $492 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
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Choose what matters most at hotels with a pool in Winchester

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Winchester Hotel Reviews

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Hotel was clean and modern. Hotel bar was fun and front desk was quick, friendly and efficient."
Jennifer 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Bristol, Connecticut
Interlaken Inn & Resort

Interlaken Inn & Resort

10/10 Excellent
"Over eight annual visits to this hotel, it has been a wonderful stay each time."
mary 1-night trip
Posted 4 days ago
Interlaken Inn & Resort
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent
"Very nice, comfortable stay. Would stay there again."
Erin 1-night trip
Posted 6 days ago
Fairfield Inn & Suites by Marriott Plainville

Frequently asked questions

What are some hotels with pools in Winchester?
Enjoy a restful stay with fast internet, smart TV and the company of your pet.: Offers a snack bar/deli, an indoor pool, and buffet. Waterfront House & Guest House Available in Winchester, CT!: Features a seasonal outdoor pool, an indoor pool, and a full-service spa. The Farmington Inn & Suites: Offers a sauna, a seasonal outdoor pool, and buffet. Delamar West Hartford: Offers a snack bar/deli, an indoor pool, and free valet parking. Extended Stay America Suites Hartford Farmington: Provides 2 bars, an indoor pool, and daily.
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 The Marina at Highland Lake, Burr Pond State Park, 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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