Hotels with Pool & Resorts in Winchester from AU$165

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Check availability on Winchester Hotels with Pool

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winchester hotels with a pool

Pool
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (171)
"Breakfast was easy and good options. "
United States
jessica
The price is AU$209
includes taxes & fees
1 Jan - 2 Jan 2026
Home2 Suites by Hilton Bristol
Indoor pool
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
2.5 star property
Plainville
8.6 out of 10, Excellent, (913)
"Great place stayed several times."
United States
Marlene D
The price is AU$165
includes taxes & fees
2 Jan - 3 Jan 2026
Fairfield Inn & Suites by Marriott Plainville
Outdoor pool
Avon Old Farms Hotel

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very good, (1000)
"Very nice place to stay"
United States
Alvero
The price is AU$202
includes taxes & fees
28 Dec - 29 Dec
Avon Old Farms Hotel
Indoor pool
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1000)
"Professional very clean and good breakfast "
United States
Piotr
The price is AU$210
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Inn & Suites Hartford/Farmington
Exterior
Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (412)
"Good hotel but expensive "
United States
Christopher
The price is AU$203
includes taxes & fees
30 Dec - 31 Dec
Residence Inn by Marriott Hartford Avon
Indoor pool
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
3.0 star property
Farmington
8.4 out of 10, Very good, (1000)
"The young woman who greeted my daughter and I was very sweet and kind. The room was clean and the beds very comfortable. Would definitely stay here again!"
United States
Lisa
The price is AU$210
includes taxes & fees
1 Jan - 2 Jan 2026
Homewood Suites by Hilton Hartford-Farmington
Indoor pool
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1003)
"Amazing stay"
United States
Marquise
The price is AU$238
includes taxes & fees
1 Jan - 2 Jan 2026
DoubleTree by Hilton Hotel Bristol, Connecticut
Seasonal outdoor pool
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (273)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is AU$301
includes taxes & fees
27 Dec - 28 Dec
Interlaken Inn & Resort
Seasonal outdoor pool
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (165)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is AU$282
includes taxes & fees
5 Jan - 6 Jan 2026
Blackberry River Inn
Reception
Simsbury 1820 House

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1003)
"Very nice room, pleasant and helpful staff"
United States
Concetta
The price is AU$299
includes taxes & fees
28 Dec - 29 Dec
Simsbury 1820 House
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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Top Winchester Hotel Reviews

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"Front desk staff was very courteous and helpful. Room was very clean. There was something different each morning for breakfast. Will definitely stay here again. "
Cornealia 1-night trip
Posted 5 days ago
Hampton Inn & Suites Hartford/Farmington

Frequently asked questions

What are some hotels with pools in Winchester?
Sheraton Hartford Hotel at Bradley Airport: Features a sauna, a seasonal outdoor pool and buffet. Extended Stay America Suites Hartford Farmington: Offers daily, an indoor pool and complimentary high-speed (wired) Internet access. Avon Old Farms Hotel: Provides a snack bar/deli, an indoor pool and buffet. Hampton Inn & Suites Hartford/Farmington: Features daily, a seasonal outdoor pool and complimentary high-speed (wired) Internet access. The Farmington Inn & Suites: Offers a seasonal outdoor pool, an indoor pool and a full-service spa.
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 Winchester Historical Society.
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.