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Find Hotels with a Pool in Winchester, CT from CA $200

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Check availability on Winchester Hotels with a Pool

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

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 $214
CA $246 total
includes taxes & fees
Oct 5 - Oct 6
Blackberry River Inn
A large indoor swimming pool with multiple seating areas and large windows.
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.
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 $186
CA $214 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites by Hilton Bristol
An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.
A hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.
An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.

3. 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 $205
CA $235 total
includes taxes & fees
Oct 31 - Nov 1
Hampton Inn & Suites Hartford/Farmington
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 Fairfield Inn & Suites hotel with a large parking lot and snow-covered ground.
A lobby with a blue sofa, a small round table, and a fireplace.

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 $174
CA $200 total
includes taxes & fees
Oct 29 - Oct 30
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 $250
CA $312 total
includes taxes & fees
Nov 2 - Nov 3
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 central decorative table.
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.

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 $275
CA $347 total
includes taxes & fees
Oct 15 - Oct 16
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 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.
A stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.

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 $205
CA $235 total
includes taxes & fees
Nov 1 - Nov 2
Residence Inn by Marriott Hartford Avon
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 $284
CA $326 total
includes taxes & fees
Oct 26 - Oct 27
Interlaken Inn & Resort
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.

9. 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 $233
CA $267 total
includes taxes & fees
Oct 15 - Oct 16
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.

10. The Litchfield Inn

The Litchfield Inn
Litchfield
CA $423
CA $486 total
includes taxes & fees
Nov 3 - Nov 4
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

8/10 Good
"Everything was good. Very comfortable stay"
Devon 1-night trip
Posted 10 hours ago
Hampton Inn & Suites Hartford/Farmington
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"The hotel has an open and calm feel that I love Appreciate SO MUCH the long-term and protected parking Food is good"
margaret 1-night trip
Posted 2 days ago
Sheraton Hartford Hotel at Bradley Airport
The Farmington Inn & Suites

The Farmington Inn & Suites

8/10 Good
"The beds were wonderful. The wallpaper was brand new and very pretty. Staff was excellent very polite, friendly and helpful. Great location. Everything went super smoothly. The rugs could use changing is the only thing I could see that would need improving."
Debra 1-night trip
Posted 2 days ago
The Farmington Inn & Suites
Interlaken Inn & Resort

Interlaken Inn & Resort

10/10 Excellent
"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."
Suzanne 5-night trip
Posted 2 days ago
Interlaken Inn & Resort
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Everything was perfect—the room, the service, the restaurant, the spa; everything was perfect. An unforgettable experience."
Moshe 2-night trip
Posted 3 weeks ago
Mayflower Inn & Spa, Auberge Collection

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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