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Winchester Hotel Guide - Hotels with Pool in Winchester, Winsted

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Check availability on Winchester Hotels with Pool

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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 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.
€195
includes taxes & fees
13 Oct - 14 Oct
Blackberry River Inn
A large, historic building with a covered porch and outdoor seating area.
A large, historic house with multiple chimneys, a covered porch, and lush greenery.
A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.
A sign for the Simsbury House, indicating it is a historic building from 1820.

2. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
€195
includes taxes & fees
4 Nov - 5 Nov
Simsbury 1820 House
A swimming pool with lounge chairs and umbrellas, surrounded by a house and trees.
A conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.
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.

3. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
  • Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness centre.
€217
includes taxes & fees
26 Oct - 27 Oct
Avon Old Farms Hotel
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
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.

4. 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.
€312
includes taxes & fees
1 Nov - 2 Nov
The Old Inn On The Green
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 lounge with a pool table, comfortable seating, and a large window offering a view of the outdoors.
A modern breakfast area with a counter, seating, and a refrigerator.

5. 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.
€134
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites by Hilton Bristol
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.
A modern kitchen with blue cabinets, a central island, and a dining area with a glass table and chairs.
A shelf with various board games and a fern plant.
An outdoor patio with wicker furniture, a glass-top table, and a barbecue grill.

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

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
€191
includes taxes & fees
20 Oct - 21 Oct
Collinsville River Escape / Fall Foliage, Deck & Yard
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.

7. The Litchfield Inn

The Litchfield Inn
Litchfield
€312
includes taxes & fees
9 Nov - 10 Nov
The Litchfield Inn
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 lobby with a blue sofa, a small round table, and a fireplace.

8. 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.
€125
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Plainville
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 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.

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.
€159
includes taxes & fees
29 Oct - 30 Oct
DoubleTree by Hilton Hotel Bristol, Connecticut
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.

10. 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.
€147
includes taxes & fees
1 Nov - 2 Nov
Residence Inn by Marriott Hartford Avon
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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

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"The motel was clean and the room we stayed in was clean and smelled good. The staff was awsome . I would recommend the Double Tree to anyone."
Carroll 3-night trip
Posted 11 hours ago
DoubleTree by Hilton Hotel Bristol, Connecticut
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

8/10 Good
"Convience"
Malcolm 1-night trip
Posted 17 hours ago
Sheraton Hartford Hotel at Bradley Airport
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 8 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 such as Highland Lake and Laurel Lanes. During your stay, visit 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 the local weather in Winchester into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 15 cm of snowfall.