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Hotels with a Pool in Winchester

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November 2025
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December 2025

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16 Nov - 17 Nov
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17 Nov - 18 Nov
Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov

Hotels with a Pool in Winchester

Hampton Inn Winchester

Winchester
£68
includes taxes & fees
26 Nov - 27 Nov
Hampton Inn Winchester

Best Western Winchester Hotel

Winchester
£68
includes taxes & fees
23 Nov - 24 Nov
Best Western Winchester Hotel

Holiday Inn Express Lexington East - Winchester by IHG

Winchester
£81
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Express Lexington East - Winchester by IHG

Comfort Inn Winchester

Winchester
£56
includes taxes & fees
6 Dec - 7 Dec
Comfort Inn Winchester

Baymont by Wyndham Winchester

Winchester
£67
includes taxes & fees
23 Nov - 24 Nov
Baymont by Wyndham Winchester

Everhome Suites Lexington - Horse Park

Lexington
£75
includes taxes & fees
17 Nov - 18 Nov
Everhome Suites Lexington - Horse Park

Natural Bridge State Resort Park

Slade
Natural Bridge State Resort Park

Home2 Suites By Hilton Richmond, Ky

Richmond
£86
includes taxes & fees
30 Nov - 1 Dec
Home2 Suites By Hilton Richmond, Ky

Hampton Inn I-75 Lexington/Hamburg Area

Lexington
£63
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn I-75 Lexington/Hamburg Area

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Lexington
£74
includes taxes & fees
27 Nov - 28 Nov
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Country Inn & Suites by Radisson, Georgetown, KY

Georgetown
£73
includes taxes & fees
9 Dec - 10 Dec
Country Inn & Suites by Radisson, Georgetown, KY

Hampton Inn Nicholasville Brannon Crossing

Nicholasville
£76
includes taxes & fees
29 Nov - 30 Nov
Hampton Inn Nicholasville Brannon Crossing

Holiday Inn Lexington - Hamburg by IHG

Lexington
£74
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Express & Suites Richmond by IHG

Richmond
£74
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express & Suites Richmond by IHG

Quality Inn Richmond

Richmond
£80
includes taxes & fees
23 Nov - 24 Nov
Quality Inn Richmond

Spark by Hilton Lexington Hamburg

Lexington
£52
includes taxes & fees
30 Nov - 1 Dec
Spark by Hilton Lexington Hamburg

GLō Best Western Lexington

Lexington
£79
includes taxes & fees
17 Nov - 18 Nov
GLō Best Western Lexington

Springhill Suites by Marriott Lexington Fritz Farm

Lexington
£97
includes taxes & fees
23 Nov - 24 Nov
Springhill Suites by Marriott Lexington Fritz Farm

Marriott Lexington Griffin Gate Golf Resort & Spa

Lexington
£88
includes taxes & fees
15 Dec - 16 Dec
Marriott Lexington Griffin Gate Golf Resort & Spa

Hampton Inn Richmond

Richmond
£80
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn Richmond
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Top landmarks in Winchester

Clark Regional Medical Center

Clark Regional Medical Center

Clark Regional Medical Center is a hospital located 1.2 mi (1.9 km) from central Winchester. There are restaurants and coffee shops in the nearby area if you need to find somewhere to eat.

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Cassell Creek Golf Course

Cassell Creek Golf Course

You might want to practise your swing at Cassell Creek Golf Course, a golf course located 4.1 mi (6.6 km) from central Winchester. If Cassell Creek Golf Course doesn't quite scratch your golfing itch, Southwind Golf Course is also nearby.

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Bluegrass Heritage Museum

Bluegrass Heritage Museum

The centre of Winchester is home to cultural attractions such as Bluegrass Heritage Museum, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Clark Regional Medical Center, Wiseman Park, and Lykins Park.

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Southwind Golf Course

Southwind Golf Course

Enjoy a round of golf in Winchester at Southwind Golf Course. While in this family-friendly area, you can savour the top-notch restaurants.

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Winchester Opera House

Winchester Opera House

You can learn about the history of Winchester when you stop by Winchester Opera House. You can enjoy the restaurants while in the area.

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Wiseman Park

Wiseman Park

Explore the great outdoors at Wiseman Park, a lovely green space in Winchester. You can enjoy the restaurants while in the area.

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Frequently asked questions

What are the best hotels with a pool in Winchester?
One of the top Winchester hotels with a pool according to guest reviews is Hampton Inn Winchester. Take advantage of laundry services and WiFi here. Pool days will also become part of your daily routine at Holiday Inn Express Lexington East - Winchester, an IHG Hotel, another highly rated option.
What are the cheapest hotels with a pool in Winchester?
You'll find some good value hotels in Winchester with a pool from £52 for your next escape. Offering laundry services and front desk services, Hampton Inn Winchester is one of the cheapest. Holiday Inn Express Lexington East - Winchester, an IHG Hotel is another option that delivers poolside fun on a budget.
What is the best time to stay in a hotel with a pool in Winchester?
If you're after the warmest weather, go in July. The temperatures are around 19ºC to 30ºC at this time. January has the coolest temperatures between -3ºC and 3ºC. For a more relaxed setting and potentially cheaper Winchester hotels with a pool, visit in January when it's less busy.
What hotels with a pool are closest to Bluegrass Heritage Museum?
With express check-out services and soundproofed rooms, Hampton Inn Winchester is one of the closest hotels with a pool to Bluegrass Heritage Museum. Best Western Winchester Hotel is another option just a quick drive away. Balance sightseeing with leisure time when you reserve a hotel in Winchester with a pool near this attraction.
What hotels with a pool are closest to Blue Grass Airport (LEX)?
Arrive, slip into your swimsuit and relax at Chateau Annette. It's roughly 3 km (2 miles) northwest of Blue Grass Airport (LEX). You can take advantage of a free cooked-to-order breakfast and complimentary breakfast here too. Another nearby option is TownePlace Suites by Marriott Lexington Keeneland/Airport. Reserve a room at one of these properties, or search for other Winchester hotels with a pool close to the airport.
Are there any hotels with a pool in Winchester with parking?
You'll find 1,172 Winchester hotels with a pool and parking. Pull up and go for a dip at Hampton Inn Winchester. Express check-out services and soundproofed rooms are included in your stay too. Or, head to Holiday Inn Express Lexington East - Winchester by IHG, where you can easily access both parking and a pool.

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