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Find Hotels with a Pool in Winchester, CT from CA $163

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Check availability on Winchester Hotels with a Pool

Tonight
Oct 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

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 bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.
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 $245
CA $282 total
includes taxes & fees
Oct 28 - Oct 29
Blackberry River Inn
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 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.

2. 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 $210 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites by Hilton Bristol
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 modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.
A spacious lobby with large windows, a central plant, and multiple hanging lights.

3. 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 $194
CA $223 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Hotel Bristol, Connecticut
A swimming pool with lounge chairs and a red door.
A modern kitchen with a central island, built-in cabinets, and a coffee station.
A hotel room with a bed, a sofa, a desk, a chair, a TV, and a lamp.
A modern lobby with a yellow sofa, marble table, and two armchairs.

4. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
Farmington
  • Indoor pool oasis for fitness and family fun just 5 minutes from attractions.
CA $213
CA $245 total
includes taxes & fees
Oct 30 - Oct 31
Homewood Suites by Hilton Hartford-Farmington
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 stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.

5. 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 $189
CA $218 total
includes taxes & fees
Nov 19 - Nov 20
Residence Inn by Marriott Hartford Avon
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 Fairfield Inn & Suites hotel with a large parking lot and snow-covered ground.
A hotel reception area with a computer desk, chairs, and a carpeted floor.

6. 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 $142
CA $163 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 central decorative table.
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.

7. 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 $239
CA $305 total
includes taxes & fees
Nov 6 - Nov 7
Avon Old Farms Hotel
A large, historic building with a covered porch and outdoor seating area.
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.
A grand foyer with a patterned carpet, a wooden staircase, a chandelier, a mounted deer head, and a large 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 $247
CA $309 total
includes taxes & fees
Oct 29 - Oct 30
Simsbury 1820 House
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 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.
CA $194
CA $223 total
includes taxes & fees
Nov 19 - Nov 20
Hampton Inn & Suites Hartford/Farmington
A poolside area with lounge chairs, a pool, and a fence.
A lobby with a chandelier, a reception desk, and a sign indicating an exit.
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.

10. The Litchfield Inn

The Litchfield Inn
Litchfield
CA $379
CA $435 total
includes taxes & fees
Nov 9 - Nov 10
The Litchfield Inn
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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

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"Excellent service"
Omobolanle 3-night trip
Posted 4 hours ago
Hampton Inn & Suites Hartford/Farmington
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 11 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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