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Hotels with Swimming Pool in Winchester, Winsted

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Check availability on Winchester Hotels with Swimming Pool

Tonight
Oct 13 - Oct 14
Tomorrow
Oct 14 - Oct 15
This weekend
Oct 16 - Oct 18
Next weekend
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 grand hallway with a chandelier, a staircase, and a table with flowers.
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.

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
P11,924
P13,713 total
includes taxes & fees
Oct 14 - Oct 15
Blackberry River 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 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.
A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.

2. 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.
P9,015
P10,368 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 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.

3. The Litchfield Inn

The Litchfield Inn
Litchfield
P19,588
P22,527 total
includes taxes & fees
Nov 2 - Nov 3
The Litchfield Inn
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 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.

4. 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.
P9,131
P10,501 total
includes taxes & fees
Oct 30 - Oct 31
Hampton Inn & Suites Hartford/Farmington
A person in a blue swimsuit relaxing in a hot tub with a pool in the background.
A spacious, well-lit event space with a glass ceiling, white tables, and a chandelier.
A large, multi-story building surrounded by dense forest, with a parking lot and a small green structure nearby.
A stone fountain with water spouting from the top, surrounded by greenery and a brick building with windows in the background.

5. Simsbury Inn

Simsbury Inn
Simsbury Center
  • Serene indoor pool escape with loungers and après-ski amenities in Simsbury Center.
P18,137
P22,229 total
includes taxes & fees
Oct 19 - Oct 20
Simsbury Inn
A swimming pool with lounge chairs and a red door.
A hotel with multiple buildings, a parking lot, and a well-maintained lawn.
A hotel room with a bed, a sofa, a desk, a chair, a TV, and a lamp.
A modern kitchen with a central island, built-in cabinets, and a coffee station.

6. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
Farmington
  • Indoor pool oasis for fitness and family fun just 5 minutes from attractions.
P10,616
P12,208 total
includes taxes & fees
Oct 25 - Oct 26
Homewood Suites by Hilton Hartford-Farmington
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.

7. 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.
P10,223
P11,757 total
includes taxes & fees
Nov 8 - Nov 9
DoubleTree by Hilton Hotel Bristol, Connecticut
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 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.

8. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
P11,005
P13,740 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 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.

9. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
  • Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness center.
P11,861
P15,012 total
includes taxes & fees
Oct 14 - Oct 15
Avon Old Farms Hotel
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.
A modern lounge with a pool table, comfortable seating, and a large window offering a view of the outdoors.

10. 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.
P8,191
P9,419 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites by Hilton Bristol
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 front desk staff was so amazing. They helped us from the moment of our arrival. Will definitely stay there again !!!"
Cindy 2-night trip
Posted 6 hours ago
DoubleTree by Hilton Hotel Bristol, Connecticut
The Farmington Inn & Suites

The Farmington Inn & Suites

8/10 Good
"The room was nice though a few stains on the bathroom ceiling and the floor creaked a lot when the people above walked around but overall it was very nice. I was looking forward to waffles for breakfast but they were out of batter and I didn’t have a lot of time to wait and find someone to refill it. I enjoyed my stay and would stay again though I thought it was a bit pricey."
Donna 1-night trip
Posted 8 hours ago
The Farmington Inn & Suites
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Location, Location, Location... perfect for departing from BDL. Restaurant was very good and bar area was clean and had a wide open area for seating."
John 1-night trip
Posted 1 day ago
Sheraton Hartford Hotel at Bradley Airport
Simsbury Inn

Simsbury Inn

8/10 Good
"The rooms are nice and very comfortable. The ground are beautiful. The breakfast buffet was often cold and the food not great."
Cynthia 4-night trip
Posted 1 day ago
Simsbury Inn
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 11 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?
The Farmington Inn & Suites: Offers a snack bar/deli, an indoor pool, and buffet. Delamar West Hartford: Features a seasonal outdoor pool, an indoor pool, and a full-service spa. Extended Stay America Suites Hartford Farmington: Offers a sauna, a seasonal outdoor pool, and buffet. Homewood Suites by Hilton Hartford-Farmington: Offers a snack bar/deli, an indoor pool, and free valet parking. Sheraton Hartford Hotel at Bradley Airport: 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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