TOP Hotels with Pool in Winchester, CT for 2026

Q: What are some hotels with pools in Winchester?

The Farmington Inn & Suites : Features daily, an indoor pool and complimentary high-speed (wired) Internet access. Sheraton Hartford Hotel at Bradley Airport : Offers a sauna, a seasonal outdoor pool and buffet. Hampton Inn & Suites Hartford/Farmington : Features a snack bar/deli, an indoor pool and free valet parking. Avon Old Farms Hotel : Provides a snack bar/deli, an indoor pool and buffet. DoubleTree by Hilton Hotel Bristol, Connecticut : Offers a snack bar/deli, a pool and daily.

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Our top choices for Winchester hotels with a pool

Home2 Suites by Hilton Bristol

Bristol

Serene hotel with an indoor pool escape just steps away from relaxing in a soothing hot tub.

฿7,075 total

includes taxes & fees

11 Jun - 12 Jun

Avon Old Farms Hotel

Avon

Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness centre.

฿7,519 total

includes taxes & fees

11 Jun - 12 Jun

Blackberry River Inn

Norfolk

Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.

฿5,859 total

includes taxes & fees

10 Jun - 11 Jun

Simsbury 1820 House

Simsbury Center

Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.

฿5,795 total

includes taxes & fees

9 Jun - 10 Jun

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

Cornwall Inn and Lodge

Cornwall Bridge

Serene seasonal outdoor pool retreat nestled near Mohawk Mountain, where pool loungers and umbrellas invite summer relaxation.

฿8,179 total

includes taxes & fees

8 Jun - 9 Jun

Fairfield Inn & Suites by Marriott Plainville

Plainville

Swim year-round at this hotel's indoor pool, with 24-hour fitness centre just steps away.

฿4,854 total

includes taxes & fees

14 Jun - 15 Jun

The Litchfield Inn

Litchfield

฿9,091 total

includes taxes & fees

15 Jun - 16 Jun

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.

฿6,856 total

includes taxes & fees

2 Jul - 3 Jul

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Choose what matters most at hotels with a pool in Winchester

Breakfast included

4 stars

Top Winchester Hotel Reviews

DoubleTree by Hilton Hotel Bristol, Connecticut

8/10 Good

"For some reason a number of channels on the TV wouldn’t come in."

Residence Inn by Marriott Hartford Avon

6/10 Okay

"This Marriott is "standard", which would be fine in that, you get pretty much the exact same middle of the road experience in any of them anywhere. However, the receptionist was so unhelpful and passive to the point of being rude and unpleasant. And, with nothing to do but watch TV, we were disappointed that the Netflix would not work (endless buffering), and again, the "delightful" receptionist had nothing to say but that's the service we offer. Oh yeah, I rate the morning coffee a C-. Having said all that, it was clean and the bedding was fine, so it did the basics I needed it to do. I wasn't there for a vacation, after all."

Frequently asked questions

What are some hotels with pools in Winchester?

The Farmington Inn & Suites: Features daily, an indoor pool and complimentary high-speed (wired) Internet access. Sheraton Hartford Hotel at Bradley Airport: Offers a sauna, a seasonal outdoor pool and buffet. Hampton Inn & Suites Hartford/Farmington: Features a snack bar/deli, an indoor pool and free valet parking. Avon Old Farms Hotel: Provides a snack bar/deli, an indoor pool and buffet. DoubleTree by Hilton Hotel Bristol, Connecticut: Offers a snack bar/deli, a pool and daily.

What is there to see and do in Winchester?

Spend some time experiencing the great outdoors at Highland Lake and Rowley Fields. During your stay, visit sights such as Burr Pond State Park, Platt Hill State Park and The Marina at Highland Lake.

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.

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