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.

Find Hotels with a Pool in Winchester, KY from CA $119

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Check availability on Winchester Hotels with a Pool

This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

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 CA $153
CA $168 total
includes taxes & fees
Nov 24 - Nov 25
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, (1,000 reviews)
"They have a really good Breakfast..."
United States
David
The price is CA $120
CA $132 total
includes taxes & fees
Dec 1 - Dec 2
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, (867 reviews)
"Room was clean beds were comfortable"
United States
Ronald
The price is CA $112
CA $123 total
includes taxes & fees
Nov 22 - Nov 23
Baymont by Wyndham Winchester
A hotel room with a large bed, a desk with a chair, a window with a view of the outside, and a wall-mounted TV.

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, (614 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 CA $143
CA $158 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express Lexington East - Winchester by IHG
A hotel room with a bed, a desk, a chair, a desk lamp, a window with curtains, an air conditioner, and a view of the outside.

5. Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (196 reviews)
"Well worth the money"
United States
Ronald
The price is CA $75
CA $83 total
includes taxes & fees
Nov 14 - Nov 15
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 CA $107
CA $118 total
includes taxes & fees
Dec 1 - Dec 2
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
Hot tub

Top Winchester Hotel Reviews

GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"The room was clean with plenty of space to stretch out. We were there for a quick overnight stay. It was quiet and we were able to rest for the next part of our trip."
Cheryl 1-night trip
Posted 1 hour ago
GuestHouse Lexington

Frequently asked questions

What are the best hotels in Winchester with outdoor pools?
If you're looking for hotels in Winchester, Kentucky, with outdoor pools, the Hampton Inn Winchester should be at the top of your list. This 3-star hotel boasts a fantastic outdoor pool that is superb for families seeking a refreshing dip during their stay. Guests rave about the friendly and helpful staff, as well as the clean and well-maintained rooms, which contribute to its impressive review rating of 9.2. Additionally, the hotel offers complimentary breakfast, free Wi-Fi, and convenient self-parking, making it an excellent choice for those who value comfort and convenience.

Another solid option is the Best Western Winchester Hotel, featuring an outdoor pool that enhances its family-friendly appeal. Rated 8.4 by travellers, this hotel is praised for its spacious and clean rooms, friendly staff, and a great breakfast selection. With free self-parking and wired internet available, guests appreciate the thoughtful amenities that add to their overall experience.

For those on a budget, the Baymont by Wyndham Winchester presents a more economical choice. Although it has a lower review score of 7.2, it still offers an outdoor pool along with free Wi-Fi and breakfast options. Guests have noted the excellent size of the rooms and the wonderful staff, making it a decent value for families looking for a fun getaway.
How much does a hotel with outdoor pool in Winchester cost?
Enjoy staying in a hotel in Winchester with an outdoor pool. You can find a great deal from CA $119 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels with outdoor pools that are close to Lykins Park?
The Hampton Inn Winchester is an excellent choice for travellers seeking a hotel with an outdoor pool close to Lykins Park. Rated 9.2 by guests, this hotel is celebrated for its friendly and helpful staff, as well as its clean and spacious rooms. Guests appreciate the convenient location and the array of amenities, including free WiFi, complimentary breakfast options, and free parking, which add to the overall value of their stay.

Another great option is the Best Western Winchester Hotel, boasting a solid review rating of 8.4. This hotel features an inviting outdoor pool along with clean and sizable rooms. Families will particularly enjoy the hearty breakfast offerings and the friendly service provided by the staff, making it a welcoming spot for both relaxation and adventure.

If you're looking for a more budget-friendly choice, consider the Baymont by Wyndham Winchester. With a traveller rating of 7.2, this hotel offers an outdoor pool and convenient amenities like free WiFi and continental breakfast. Guests have noted the excellent room sizes and the wonderful service from the staff, making it a practical option for families wanting to enjoy their time near Lykins Park without breaking the bank.
Is it cheaper to book flights and a hotel in Winchester as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel with an outdoor pool in Winchester for you.
How can I save on a hotel in Winchester with Expedia?
Before booking your Winchester hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access instant discounts with Member Prices as well as member-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

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