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Winchester Hotel Guide - Hotels with Pool in Winchester, Winsted

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Check availability on Winchester Hotels with Pool

Tonight
25 Aug - 26 Aug
Tomorrow
26 Aug - 27 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Winchester hotels with a pool

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
€187
includes taxes & fees
31 Aug - 1 Sept
Blackberry River Inn

2. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
  • Dive into an indoor pool oasis year-round at this charming Simsbury bed and breakfast.
€181
includes taxes & fees
26 Aug - 27 Aug
Simsbury 1820 House

3. Sunny Peace Homestay

Sunny Peace Homestay
Harwinton
€178
includes taxes & fees
26 Aug - 27 Aug
Sunny Peace Homestay

4. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
  • Dive into pure refreshment at this seasonal outdoor pool oasis with sauna and fitness centre.
€169
includes taxes & fees
3 Sept - 4 Sept
Avon Old Farms Hotel

5. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
Bristol
  • Serene hotel with an indoor pool escape just steps away from relaxing in a soothing hot tub.
€130
includes taxes & fees
6 Sept - 7 Sept
Home2 Suites by Hilton Bristol

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.
€150
includes taxes & fees
13 Sept - 14 Sept
Residence Inn by Marriott Hartford Avon

7. The Litchfield Inn

The Litchfield Inn
Litchfield
€281
includes taxes & fees
26 Aug - 27 Aug
The Litchfield Inn

8. Hampton Inn & Suites Hartford/Farmington

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.
€137
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Hartford/Farmington

9. Cornwall Inn and Lodge

Cornwall Inn and Lodge
Cornwall Bridge
  • Serene seasonal outdoor pool retreat nestled near Mohawk Mountain, where pool loungers and umbrellas invite summer relaxation.
€208
includes taxes & fees
26 Aug - 27 Aug
Cornwall Inn and Lodge

10. Simsbury Inn

Simsbury Inn
Simsbury Center
  • Serene indoor pool escape with loungers and après-ski amenities in Simsbury Centre.
€254
includes taxes & fees
16 Sept - 17 Sept
Simsbury Inn
View all properties

Choose what matters most at hotels with a pool in Winchester

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Winchester Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

8/10 Good
"Perfect hotel for long layover or early departure"
Gerald 1-night trip
Posted 5 hours ago
Sheraton Hartford Hotel at Bradley Airport
Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Good"
Jeremy J 3-night trip
Posted 1 day ago
Avon Old Farms Hotel
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

8/10 Good
"Excellent breakfast"
Maureen O 6-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Plainville
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Beautiful property with lovely pool and spa area. The rooms are beautifully decorated. The staff are all friendly, welcoming, and very helpful. The grounds and gardens are well maintained. The hiking trail is highly recommended. My room in the main house was a bit noisy; the room above mine appeared to be a utility room that was active early in the morning. I could hear footsteps throughout the day. The dinner was overrated, but the breakfast and lunch were delicious."
Mary 3-night trip
Posted 4 days 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: Features a snack bar/deli, an indoor pool and buffet. Waterfront House & Guest House Available in Winchester, CT!: Features a sauna, a seasonal outdoor pool and buffet. Sheraton Hartford Hotel at Bradley Airport: Provides a seasonal outdoor pool, an indoor pool and a full-service spa. Homewood Suites by Hilton Hartford-Farmington: Features a snack bar/deli, a pool and daily. The Farmington Inn & Suites: Offers daily, an indoor pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Winchester?
Make a point to visit attractions such as Highland Lake and Laurel Lanes. During your stay, visit sights such as Burr Pond State Park, The Marina at Highland Lake and Platt Hill State Park.
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.