The Best Hotels with a Pool in Winchester, CT from NT$4,739 in 2026

Q: What are some hotels with pools in Winchester?

The Farmington Inn & Suites : Features a sauna, a seasonal outdoor pool, and buffet. Avon Old Farms Hotel : Hotel located near Lake Compounce. Features a snack bar/deli, an indoor pool, and free valet parking. Delamar West Hartford : Offers daily, an indoor pool, and complimentary wired internet access. DoubleTree by Hilton Hotel Bristol, Connecticut : Provides a snack bar/deli, an indoor pool, and buffet. Hampton Inn & Suites Hartford/Farmington : Offers a snack bar/deli, a pool, and daily.

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Our top choices for Winchester hotels with a pool

The Litchfield Inn

Litchfield

NT$9,589 total

includes taxes & fees

Jul 14 - Jul 15

Interlaken Inn & Resort

Lakeville

Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.

Simsbury Inn

Simsbury Center

Serene indoor pool escape with loungers and après-ski amenities in Simsbury Center.

NT$11,315 total

includes taxes & fees

Jul 7 - Jul 8

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.

NT$5,507 total

includes taxes & fees

Aug 4 - Aug 5

M3 Romantic Suite | Living area | 43-inch LCD TV with digital channels, streaming services

Blackberry River Inn

Norfolk

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

NT$5,720 total

includes taxes & fees

Jul 8 - Jul 9

Homewood Suites by Hilton Hartford-Farmington

Farmington

Indoor pool oasis for fitness and family fun just 5 minutes from attractions.

NT$5,257 total

includes taxes & fees

Jul 12 - Jul 13

Simsbury 1820 House

Simsbury Center

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

NT$9,331 total

includes taxes & fees

Jul 7 - Jul 8

Seasonal outdoor pool, pool umbrellas, sun loungers

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.

NT$6,249 total

includes taxes & fees

Jul 12 - Jul 13

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Choose what matters most at hotels with a pool in Winchester

Breakfast included

4 stars

Top Winchester Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent

"EXTREMELY EASE for very early morning flight to get thru security at BDL…literally steps away, no shuttle needed."

Avon Old Farms Hotel

10/10 Excellent

"My husband and I booked a last-minute weekend getaway at Avon Old Farms Inn, and we absolutely loved every minute of our stay. The atmosphere was so relaxing that it almost felt like being on a cruise, everything was taken care of, and we were able to truly unwind. A special thank you to Chef Chris, whose culinary skills made every meal exceptional. The food was beautifully prepared and absolutely delicious. We also want to recognize JG, our server and bartender, who was warm, friendly, and genuinely delightful. His outstanding service and personality made our stay even more enjoyable and truly memorable. We can't wait to return and highly recommend Avon Old Farms Inn for anyone looking for a relaxing and welcoming getaway!"

Frequently asked questions

What are some hotels with pools in Winchester?

The Farmington Inn & Suites: Features a sauna, a seasonal outdoor pool, and buffet. Avon Old Farms Hotel: Hotel located near Lake Compounce. Features a snack bar/deli, an indoor pool, and free valet parking. Delamar West Hartford: Offers daily, an indoor pool, and complimentary wired internet access. DoubleTree by Hilton Hotel Bristol, Connecticut: Provides a snack bar/deli, an indoor pool, and buffet. Hampton Inn & Suites Hartford/Farmington: Offers a snack bar/deli, a 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 Platt Hill State Park, Burr Pond State Park, and The Marina at Highland Lake.

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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