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Check availability on Winchester Hotels with a Pool

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16

Our top choices for Winchester hotels with a pool

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

1. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (200 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is ￥29,308
￥33,704 total
includes taxes & fees
Aug 9 - Aug 10
Blackberry River Inn
Seasonal outdoor pool

2. The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.2 out of 10, Wonderful, (1,003 reviews)
The price is ￥47,777
￥54,943 total
includes taxes & fees
Aug 16 - Aug 17
The Litchfield Inn
Seasonal outdoor pool, pool umbrellas, sun loungers

3. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (454 reviews)
  • cleanliness
    Splash into mountain adventures with a rejuvenating seasonal outdoor pool and hot tub retreat just steps from scenic trails.
The price is ￥22,524
￥25,902 total
includes taxes & fees
Aug 16 - Aug 17
Residence Inn by Marriott Hartford Avon
Indoor pool, sun loungers

4. Simsbury Inn

Simsbury Inn
3.5 star property
Simsbury Center
9.2 out of 10, Wonderful, (305 reviews)
  • cleanliness
    Serene indoor pool escape with loungers and après-ski amenities in Simsbury Center.
The price is ￥45,489
￥55,752 total
includes taxes & fees
Aug 3 - Aug 4
Simsbury Inn
Indoor pool

5. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Swim and unwind at this stylish retreat where guests adore the indoor pool and hot tub for year-round aquatic relaxation.
The price is ￥22,200
￥25,530 total
includes taxes & fees
Aug 16 - Aug 17
Hampton Inn & Suites Hartford/Farmington
Outdoor pool

6. Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1,004 reviews)
  • cleanliness
    Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness center.
The price is ￥30,328
￥38,316 total
includes taxes & fees
Aug 5 - Aug 6
Avon Old Farms Hotel
Indoor pool

7. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
3.0 star property
Farmington
8.4 out of 10, Very Good, (1,006 reviews)
  • cleanliness
    Indoor pool oasis for fitness and family fun just 5 minutes from attractions.
The price is ￥23,103
￥26,569 total
includes taxes & fees
Aug 9 - Aug 10
Homewood Suites by Hilton Hartford-Farmington
Exterior

8. Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
The price is ￥29,749
￥36,926 total
includes taxes & fees
Aug 3 - Aug 4
Simsbury 1820 House
Indoor pool

9. Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Swim year-round at this hotel's indoor pool, with 24-hour fitness center just steps away.
The price is ￥17,944
￥20,636 total
includes taxes & fees
Aug 9 - Aug 10
Fairfield Inn & Suites by Marriott Plainville
Indoor pool

10. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Serene indoor saltwater pool retreat creates an oasis of relaxation with a nearby hot tub in this upscale Connecticut hotel.
The price is ￥25,685
￥29,538 total
includes taxes & fees
Aug 16 - Aug 17
DoubleTree by Hilton Hotel Bristol, Connecticut
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"It helped tremendously that the hotel was connected to the airport. I would highly encourage others to consider going that route if you have an early morning flight."
Lynn 1-night trip
Posted 3 hours ago
Sheraton Hartford Hotel at Bradley Airport
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"The best"
vera alice 2-night trip
Posted 7 hours ago
Mayflower Inn & Spa, Auberge Collection

Frequently asked questions

What are some hotels with pools in Winchester?
Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR: Offers a sauna, a seasonal outdoor pool, and buffet. The Farmington Inn & Suites: Features a snack bar/deli, an indoor pool, and buffet. Sheraton Hartford Hotel at Bradley Airport: Provides daily, an indoor pool, and complimentary wired internet access. Avon Old Farms Hotel: Features a seasonal outdoor pool, an indoor pool, and a full-service spa. Homewood Suites by Hilton 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.