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Find Hotels with a Pool in Winchester, CT from CA $154

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Check availability on Winchester Hotels with a Pool

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

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.

1. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (251 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is CA $242
CA $278 total
includes taxes & fees
Nov 15 - Nov 16
Blackberry River Inn
An indoor swimming pool with a 'No Diving' sign, a glass enclosure, and a tiled wall with a 'No Diving' sign.

2. Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.4 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Swim year-round at this hotel's indoor pool, with 24-hour fitness centre just steps away.
The price is CA $134
CA $154 total
includes taxes & fees
Nov 19 - Nov 20
Fairfield Inn & Suites by Marriott Plainville
A large indoor swimming pool with multiple seating areas and large windows.

3. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (284 reviews)
  • cleanliness
    Serene hotel with an indoor pool escape just steps away from relaxing in a soothing hot tub.
The price is CA $182
CA $210 total
includes taxes & fees
Nov 8 - Nov 9
Home2 Suites by Hilton Bristol
A swimming pool with lounge chairs and a covered seating area, surrounded by multi-story buildings with visible windows and a brick facade.

4. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (465 reviews)
  • cleanliness
    Splash into mountain adventures with a rejuvenating seasonal outdoor pool and hot tub retreat just steps from scenic trails.
The price is CA $178
CA $205 total
includes taxes & fees
Nov 19 - Nov 20
Residence Inn by Marriott Hartford Avon
A swimming pool with lounge chairs and a red door.

5. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
3.0 star property
Farmington
8.4 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Indoor pool oasis for fitness and family fun just 5 minutes from attractions.
The price is CA $236
CA $272 total
includes taxes & fees
Nov 12 - Nov 13
Homewood Suites by Hilton Hartford-Farmington
A large, historic building with a covered porch and outdoor seating area.

6. Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,003 reviews)
  • cleanliness
    Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
The price is CA $250
CA $312 total
includes taxes & fees
Nov 12 - Nov 13
Simsbury 1820 House
An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.

7. 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 CA $188
CA $216 total
includes taxes & fees
Nov 19 - Nov 20
Hampton Inn & Suites Hartford/Farmington
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.

8. 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 CA $205
CA $236 total
includes taxes & fees
Nov 8 - Nov 9
DoubleTree by Hilton Hotel Bristol, Connecticut
A poolside area with lounge chairs, a pool, and a fence.

9. The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.2 out of 10, Wonderful, (1,000 reviews)
The price is CA $389
CA $448 total
includes taxes & fees
Nov 9 - Nov 10
The Litchfield Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a house and trees.

10. Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness centre.
The price is CA $238
CA $304 total
includes taxes & fees
Nov 12 - Nov 13
Avon Old Farms Hotel
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.
View all properties

Choose what matters most at hotels with a pool in Winchester

Breakfast included
4 stars

Top Winchester Hotel Reviews

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

8/10 Good
"Clean and nice property Helpful staff"
Raed 1-night trip
Posted 11 hours ago
Hampton Inn & Suites Hartford/Farmington
Avon Old Farms Hotel

Avon Old Farms Hotel

8/10 Good
"Avon Old Farms is in old property that has been very well maintained. It is charming, has comfortable seating throughout with small libraries for reading. It is light and airy. The breakfast that is provided as part of the room is adequate. The biggest negative is the staff, primarily the staff at the front desk. They are courteous but they do not extend themselves or demonstrate any warmth or enthusiasm that you are there. When you walk up, they say 'yes?' No "welcome to Avon Old Farms" or " I hope that your trip went well" or "if there's anything that we can do to make you stay more enjoyable, please let us know". They proceeded to perform the necessary check-in steps, answered my question about room service (not available) without adding any suggestions for dinner alternatives. Their attitude is that they're there because they have to be and that they are courteous and doing what they have to do to keep their jobs. That part was very disappointing. The rest of the hotel was charming, gracious, and I would stay there again in spite of the front office coolness."
Nikki 3-night trip
Posted 3 days ago
Avon Old Farms Hotel

Frequently asked questions

What are some hotels with pools in Winchester?
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!: Features a seasonal outdoor pool, an indoor pool, and a full-service spa. The Farmington Inn & Suites: Offers a sauna, a seasonal outdoor pool, and buffet. Delamar West Hartford: Offers a snack bar/deli, an indoor pool, and free valet parking. Extended Stay America Suites Hartford Farmington: 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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