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Find Hotels with a Pool in Winchester, CT from CA $170

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Check availability on Winchester Hotels with a Pool

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
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 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.

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
CA $233
CA $268 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.
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.
An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.
A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.

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 $203
CA $233 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 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.
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 $184
CA $212 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 room with a sofa, two small tables, a TV, a desk, and a mirror.
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.

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 $148
CA $170 total
includes taxes & fees
Nov 8 - Nov 9
Fairfield Inn & Suites by Marriott Plainville
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 conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.

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 $248
CA $316 total
includes taxes & fees
Nov 2 - Nov 3
Avon Old Farms Hotel
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.
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.

6. 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 $207
CA $238 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 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
CA $406
CA $467 total
includes taxes & fees
Nov 19 - Nov 20
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 grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.

8. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
CA $246
CA $307 total
includes taxes & fees
Nov 19 - Nov 20
Simsbury 1820 House
A swimming pool with lounge chairs and a covered seating area, surrounded by multi-story buildings with visible windows and a brick facade.
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.
A hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.

9. 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 $191
CA $219 total
includes taxes & fees
Nov 19 - Nov 20
Residence Inn by Marriott Hartford Avon
A swimming pool with lounge chairs and umbrellas, surrounded by trees.
A dining area with a round table, chairs, a fireplace, and a variety of plants.
A large, two-story house with a wrap-around porch, a central entrance, and a flag.
A spacious living room with a large sectional sofa, a round coffee table, and a chandelier. There are large windows with curtains, a fireplace, and a view of greenery outside.

10. Belden House & Mews

Belden House & Mews
Litchfield Historic District
  • Seasonal outdoor pool complemented by massages and spa treatments elevates relaxation at this mountain retreat.
CA $592
CA $737 total
includes taxes & fees
Nov 19 - Nov 20
Belden House & Mews
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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 3 hours ago
DoubleTree by Hilton Hotel Bristol, Connecticut
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"I can always count on this hotel whenever I'm visiting Hartford! It's the perfect place to stay before catching an early morning flight. The location is convenient, the rooms are consistently clean, cozy, and wonderfully quiet, making it easy to get a good night's rest before traveling. The staff is always delightful, welcoming, and friendly. It's comforting to know I have a reliable place to stay, and I look forward to returning each time. Highly recommend!"
Shelley 1-night trip
Posted 21 hours ago
Sheraton Hartford Hotel at Bradley Airport
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 3 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 5 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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