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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 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
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 dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.
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 $234
CA $269 total
includes taxes & fees
Nov 2 - Nov 3
Blackberry River Inn
An indoor swimming pool with a 'No Diving' sign, a glass enclosure, and a tiled wall with a 'No Diving' sign.
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.
A lobby with a blue sofa, a small round table, and a fireplace.

2. 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 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.

3. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
CA $248
CA $309 total
includes taxes & fees
Nov 4 - Nov 5
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 reception desk.
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.

4. 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 $241
CA $308 total
includes taxes & fees
Nov 6 - Nov 7
Avon Old Farms Hotel
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.
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.
A spacious lobby with large windows, a central plant, and multiple hanging lights.

5. 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 $208
CA $239 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 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 lobby with a chandelier, a reception desk, and a sign indicating an exit.

6. The Litchfield Inn

The Litchfield Inn
Litchfield
CA $408
CA $469 total
includes taxes & fees
Nov 15 - Nov 16
The Litchfield Inn
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.
A stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.

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 $203
CA $234 total
includes taxes & fees
Nov 1 - Nov 2
Residence Inn by Marriott Hartford Avon
A swimming pool with lounge chairs and umbrellas, surrounded by trees.
A modern house with a white exterior, two wooden doors, and a grey awning.
A dining area with a round table, chairs, a fireplace, and a variety of plants.
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.

8. 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 $611
CA $760 total
includes taxes & fees
Nov 1 - Nov 2
Belden House & Mews
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.
A shelf with various board games and a fern plant.
An outdoor patio with wicker furniture, a glass-top table, and a barbecue grill.
A bedroom with a bed, two bedside tables with lamps, a dresser, and a door.

9. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
CA $253
CA $320 total
includes taxes & fees
Oct 29 - Oct 30
Collinsville River Escape / Fall Foliage, Deck & Yard
A dining area with round tables set for two, a fireplace, and a mural on the wall.
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.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

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 $410
CA $495 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

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 20 hours ago
Interlaken Inn & Resort
The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"Thin walls, I'll just say that you may hear sounds that you may or may not mind hearing."
Roger 2-night trip
Posted 2 days ago
The Farmington Inn & Suites
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 3 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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