A tranquil lake with a stone tower, surrounded by autumn-colored trees and a clear sky.

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Check availability on Winsted Hotels with a Pool

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Winsted 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 dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
AED 512
AED 589 total
includes taxes & fees
18 Oct - 19 Oct
Blackberry River Inn
A person in a blue swimsuit relaxing in a hot tub with a pool in the background.
A large, multi-story building surrounded by dense forest, with a parking lot and a small green structure nearby.
A spacious, well-lit event space with a glass ceiling, white tables, and a chandelier.
A brick building with a covered patio, a fountain, and a staircase leading to a second floor.

2. Simsbury Inn

Simsbury Inn
Simsbury Center
  • Serene indoor pool escape with loungers and après-ski amenities in Simsbury Center.
AED 1,062
AED 1,301 total
includes taxes & fees
7 Oct - 8 Oct
Simsbury Inn
An indoor swimming pool with a tiled floor, a pool ladder, and a few lounge chairs.
A breakfast buffet with various food items and condiments.
A modern lobby with a reception desk, seating area, and a large wall-mounted screen.
A modern hotel with a flat roof, large windows, and a covered entrance.

3. Springhill Suites Marriott Airport

Springhill Suites Marriott Airport
Windsor Locks
  • Refresh in this tranquil indoor pool with heated waters that create an escape for all-season swimming and family enjoyment.
AED 459
AED 528 total
includes taxes & fees
1 Nov - 2 Nov
Springhill Suites Marriott Airport
An indoor swimming pool with clear water, a lifeguard chair, and a changing room with a shower.
A hotel room with a bed, a sofa, a desk with a chair, a TV, and a lamp.
A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.
A Holiday Inn Express hotel with a covered entrance, multiple floors, and a landscaped driveway.

4. Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG
Windsor Locks
  • Unwind in a pristine indoor pool sanctuary where airport convenience meets comfort at this Hartford retreat hotel.
AED 448
AED 515 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express & Suites Bradley Airport by IHG
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 foyer with a patterned carpet, a wooden staircase, a chandelier, a mounted deer head, and a large 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.
AED 643
AED 803 total
includes taxes & fees
2 Nov - 3 Nov
Simsbury 1820 House
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.
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.

6. 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.
AED 528
AED 607 total
includes taxes & fees
1 Nov - 2 Nov
Residence Inn by Marriott Hartford Avon
A swimming pool with clear water, surrounded by a fence and trees.
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.
A long wooden table with potted plants and candle holders in a modern interior setting.

7. The Litchfield Inn

The Litchfield Inn
Litchfield
AED 1,140
AED 1,311 total
includes taxes & fees
2 Nov - 3 Nov
The Litchfield Inn
An indoor swimming pool area with tiled flooring, lounge chairs, and tables with umbrellas.
A modern hotel room with a seating area, a flat-screen TV, and a dining table.
A modern hotel room with a dining area, seating arrangements, and a large TV screen.
A modern living room with a grey sofa, a black exercise bike, and a large mirror reflecting the room.

8. Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport
Windsor
  • Dive into relaxation at this Connecticut hotel with a refreshing indoor pool, steps from the New England Air Museum.
AED 476
AED 547 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn Hartford/Airport
An indoor swimming pool with clear glass walls, a blue pool area, and sunlit seating areas.
A bar area with a long counter, multiple bar stools, and a television mounted above the bar. There are bottles and glasses on the counter, and the room has large windows with blinds.
A modern reception area with a digital display, a reception desk, and a seating area with patterned ottomans.
A bar area with high stools, a counter, and a television mounted on the wall.

9. DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport
Windsor Locks
  • Discover a hotel with a refreshing indoor pool sanctuary, complemented by 24-hour fitness options and airport shuttle convenience.
AED 453
AED 521 total
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Hartford - Bradley Airport
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.

10. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
  • Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness center.
AED 708
AED 894 total
includes taxes & fees
15 Oct - 16 Oct
Avon Old Farms Hotel
View all properties

Choose what matters most at hotels with a pool in Winsted

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Winsted Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 8 hours ago
Quality Inn Great Barrington
Springhill Suites Marriott Airport

Springhill Suites Marriott Airport

8/10 Good
"It was clean, the staff was great. The rooms are a little out dated but over all a nice hotel."
Sandy 6-night trip
Posted 2 days ago
Springhill Suites Marriott Airport
Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG

8/10 Good
"This hotel was very convenient and the beds are wonderful! The staff tries to keep it clean, though our bathroom could hav3e used a little bit more cleaning around the edges of the shower, etc. All in all, an OK stay."
Candice 2-night trip
Posted 3 days ago
Holiday Inn Express & Suites Bradley Airport by IHG

Frequently asked questions

What are some hotels with pools in Winsted?
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!: Offers a snack bar/deli, a pool, and buffet. Quality Inn Great Barrington: Features daily, an indoor pool, and complimentary wired internet access. The Farmington Inn & Suites: Features free self parking, an indoor pool, and a 24-hour fitness center. Homewood Suites by Hilton Hartford-Farmington: Provides a sauna, a seasonal outdoor pool, and buffet.
What is there to see and do in Winsted?
Make a point to visit attractions like Highland Lake and Laurel Lanes. Discover sights such as Burr Pond State Park, The Marina at Highland Lake, and Northwestern Connecticut Community College Library during your stay.
When is the best time to book a hotel with a pool in Winsted?
Taking into account the local weather in Winsted is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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 Winsted are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.