Default HTG hotel image

Find Hotels with a Pool in Winchester, CT from CA $185

  • 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 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 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 $213
CA $245 total
includes taxes & fees
Oct 4 - Oct 5
Blackberry River Inn
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.
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.

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 $213 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 Fairfield Inn & Suites hotel with a large parking lot and snow-covered ground.
A hotel room with a sofa, two small tables, a TV, a desk, and a mirror.

3. 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 $161
CA $185 total
includes taxes & fees
Oct 4 - Oct 5
Fairfield Inn & Suites by Marriott Plainville
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 hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

4. 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 $220
CA $253 total
includes taxes & fees
Oct 29 - Oct 30
DoubleTree by Hilton Hotel Bristol, Connecticut
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A wooden deck with a swing chair and a bench overlooking a lake.
A modern hotel room with a bed, sofa, leather chair, and a small table.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

5. 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 $283
CA $325 total
includes taxes & fees
Oct 26 - Oct 27
Interlaken Inn & Resort
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.

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 $273
CA $345 total
includes taxes & fees
Oct 25 - Oct 26
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.
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 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 $204
CA $235 total
includes taxes & fees
Nov 1 - Nov 2
Residence Inn by Marriott Hartford Avon
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 large, historic house with multiple chimneys, a covered porch, and lush greenery.

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 $259
CA $322 total
includes taxes & fees
Nov 1 - Nov 2
Simsbury 1820 House
An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.
A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.
A hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.

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 $209
CA $240 total
includes taxes & fees
Oct 31 - Nov 1
Hampton Inn & Suites Hartford/Farmington
A swimming pool with clear water, surrounded by a fence and trees.
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.
A rustic bedroom with a large bed, wooden headboard, and a wooden floor. There is a chair and a small table with a lamp.

10. The Litchfield Inn

The Litchfield Inn
Litchfield
CA $477
CA $549 total
includes taxes & fees
Nov 1 - Nov 2
The Litchfield Inn
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

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"The hotel and the staff was excellent thank you so much."
Johnny 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut
Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"We will be returning in May for our Anniversary. Very pleased with everything…"
Denise 2-night trip
Posted 6 days ago
Avon Old Farms Hotel
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.

Explore a world of travel with Expedia