Default HTG hotel image

Find Hotels with a Pool in Winchester, CT from CA $201

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with a Pool

Tonight
Oct 11 - Oct 12
Tomorrow
Oct 12 - Oct 13
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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 cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.
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.

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
CA $271
CA $312 total
includes taxes & fees
Oct 13 - Oct 14
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 spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.
A hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.

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 $213
CA $245 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 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.
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 $186
CA $214 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 lobby with a blue sofa, a small round table, and a fireplace.
A hotel room with a sofa, two small tables, a TV, a desk, and a mirror.

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 $201 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 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.
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 $247
CA $309 total
includes taxes & fees
Nov 2 - Nov 3
Simsbury 1820 House
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
A modern lobby with a reception desk, seating area, and a large decorative light fixture.
A spacious lobby with large windows, a central plant, and multiple hanging lights.
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 $233
CA $268 total
includes taxes & fees
Oct 18 - Oct 19
DoubleTree by Hilton Hotel Bristol, Connecticut
A swimming pool with lounge chairs and umbrellas, surrounded by a house and trees.
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.
A conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.

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 $275
CA $347 total
includes taxes & fees
Oct 19 - Oct 20
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.
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.
A hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.

8. 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 $236 total
includes taxes & fees
Nov 1 - Nov 2
Residence Inn by Marriott Hartford Avon
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 long wooden table with potted plants and candle holders in a modern interior setting.

9. The Litchfield Inn

The Litchfield Inn
Litchfield
CA $433
CA $498 total
includes taxes & fees
Nov 3 - Nov 4
The Litchfield Inn
A dining area with round tables set for two, a fireplace, and a mural on the wall.
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.
A white two-story house with a front door, windows, and a chimney.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

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 $413
CA $499 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
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

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

10/10 Excellent
"Nice place close to west Hartford. Staff was helpful."
Ronald 1-night trip
Posted 2 days ago
Homewood Suites by Hilton Hartford-Farmington
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 9 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 1 month 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.

Explore a world of travel with Expedia