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 $105

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Check availability on Winchester Hotels with a Pool

This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Our top choices for Winchester hotels with a pool

Seasonal outdoor pool

1. Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (477 reviews)
  • cleanliness
    Seasonal outdoor pool creates refreshing summer sanctuary at this hotel, offering a peaceful retreat in the heart of Winchester.
The price is CA $137
CA $151 total
includes taxes & fees
Aug 16 - Aug 17
Hampton Inn Winchester
Seasonal outdoor pool

2. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,006 reviews)
  • cleanliness
    Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
The price is CA $120
CA $132 total
includes taxes & fees
Aug 11 - Aug 12
Best Western Winchester Hotel
Indoor pool

3. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (832 reviews)
  • cleanliness
    Refreshing year-round aquatic escape awaits at this Winchester hotel's indoor pool, complemented by a modern fitness centre.
The price is CA $106
CA $117 total
includes taxes & fees
Aug 9 - Aug 10
Baymont by Wyndham Winchester
Indoor pool

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, (588 reviews)
  • cleanliness
    Dive into aquatic bliss in this rural retreat with an indoor pool open from dawn to dusk.
The price is CA $153
CA $168 total
includes taxes & fees
Sep 6 - Sep 7
Holiday Inn Express Lexington East - Winchester by IHG
Indoor pool, sun loungers

5. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,188 reviews)
  • cleanliness
    Splash into relaxation at the indoor pool oasis, where sun loungers invite a day of rejuvenating lounging.
The price is CA $125
CA $145 total
includes taxes & fees
Aug 10 - Aug 11
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Indoor pool

6. Hotel Lex and Conference Center, Trademark Collection

Hotel Lex and Conference Center, Trademark Collection
3.0 star property
Lexington
8.0 out of 10, Very good, (787 reviews)
  • cleanliness
    Dive into indoor pool bliss at this Lexington hotel where family fun and fitness unite.
The price is CA $118
CA $137 total
includes taxes & fees
Aug 12 - Aug 13
Hotel Lex and Conference Center, Trademark Collection
Indoor pool

7. Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg
2.5 star property
Lexington
8.8 out of 10, Excellent, (555 reviews)
  • cleanliness
    Refreshing swims await at this Lexington hotel's indoor pool, with convenient access to local attractions and premium amenities.
The price is CA $91
CA $105 total
includes taxes & fees
Aug 16 - Aug 17
Spark by Hilton Lexington Hamburg
Indoor pool

8. Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area
2.5 star property
Lexington
8.6 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Splash into comfort at this Lexington hotel with an indoor pool open from 7 AM to 11 PM daily.
The price is CA $114
CA $132 total
includes taxes & fees
Aug 12 - Aug 13
Hampton Inn I-75 Lexington/Hamburg Area
Indoor pool

9. Hyatt Place Lexington

Hyatt Place Lexington
3.0 star property
Lexington
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Tranquil indoor pool sanctuary awaits with rejuvenating waters to complement your stay at this perfectly located Lexington hotel.
The price is CA $142
CA $164 total
includes taxes & fees
Aug 12 - Aug 13
Hyatt Place Lexington
Indoor pool

10. Ramada Limited Mount Sterling

Ramada Limited Mount Sterling
2.0 star property
Mount Sterling
7.0 out of 10, Good, (839 reviews)
  • cleanliness
    Dive into refreshing laps at this hotel's sparkling indoor pool before unwinding in the hot tub.
The price is CA $107
CA $118 total
includes taxes & fees
Aug 11 - Aug 12
Ramada Limited Mount Sterling
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.
View all properties

Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub

Top Winchester Hotel Reviews

Hyatt Place Lexington

Hyatt Place Lexington

10/10 Excellent
"Large room for our toddler to run around but sadly the carpet turned her feet/socks black. The shower head was also nearly impossible to fully turn off which explains the rust on the drain."
Daniel 1-night trip
Posted 3 hours ago
Hyatt Place 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 $105 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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