An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Hotels with Pool & Resorts in Winchester from NZ$142

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Check availability on Winchester Hotels with Pool

Our top choices for Winchester hotels with a pool

A swimming pool with a no diving sign, lounge chairs, and a building with a no diving sign.

1. Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (487 reviews)
"Close to Red River Gorge hiking."
United States
kelly
The price is NZ$225
includes taxes & fees
26 Nov - 27 Nov
Hampton Inn Winchester
A rectangular swimming pool with a white edge, surrounded by a concrete deck and a low white wall.

2. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,002 reviews)
"They have a really good Breakfast..."
United States
David
The price is NZ$169
includes taxes & fees
8 Dec - 9 Dec
Best Western Winchester Hotel
A swimming pool with wooden walls and large windows offering views of greenery.

3. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.4 out of 10, Good, (868 reviews)
"Room was clean beds were comfortable"
United States
Ronald
The price is NZ$158
includes taxes & fees
19 Nov - 20 Nov
Baymont by Wyndham Winchester
An indoor swimming pool with a lifeguard chair, a pool ladder, and a sign indicating no diving allowed.

4. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (617 reviews)
"This is one of the nicest and cleanest Holiday Inns I’ve ever been to. Very friendly staff too."
United States
Stephen
The price is NZ$202
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express Lexington East - Winchester by IHG
A reception area with a counter, a red door, and a 'No Smoking' sign.

5. Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (201 reviews)
"Room was clean"
United States
Kristie
The price is NZ$113
includes taxes & fees
14 Dec - 15 Dec
Value Stay
An indoor swimming pool with tiled flooring, orange walls, and potted plants.

6. Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (397 reviews)
"Pool was closed other than that overall good hotel"
United States
james
The price is NZ$100
includes taxes & fees
14 Dec - 15 Dec
Comfort Inn Winchester
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
Spa pool

Top Winchester Hotel Reviews

GuestHouse Lexington

GuestHouse Lexington

8/10 Good
"Neat place"
Chase 1-night trip
Posted 5 hours ago
GuestHouse Lexington

Frequently asked questions

What are some accommodation options with pools in Winchester?
Best Western Winchester Hotel: Features full, a seasonal outdoor pool and free self parking. Baymont by Wyndham Winchester: Offers daily, a pool and free self parking.
What is there to see and do in Winchester?
Spend some time experiencing the great outdoors at College Park and GRCHS Baseball Field. During your stay, visit sights such as Bluegrass Heritage Museum, Cassell Creek Golf Course and Winchester Opera House. You'll also discover lots of options for restaurants in Winchester.
When is the best time to book a hotel with a pool in Winchester?
You may want to consider a place to stay that has an outdoor pool if you'll be visiting Winchester in the hottest months of July, August or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 4°C.

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