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.

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Our top choices for Winchester hotels with a pool

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,003 reviews)
  • cleanliness
    Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
The price is CA $128
CA $141 total
includes taxes & fees
Jun 28 - Jun 29
Best Western Winchester Hotel

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (812 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 $107
CA $118 total
includes taxes & fees
Jun 23 - Jun 24
Baymont by Wyndham Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (471 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 $198
CA $219 total
includes taxes & fees
Jun 24 - Jun 25
Hampton Inn Winchester

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.2 out of 10, Wonderful, (571 reviews)
  • cleanliness
    Dive into aquatic bliss in this rural retreat with an indoor pool open from dawn to dusk.
The price is CA $173
CA $190 total
includes taxes & fees
Jul 22 - Jul 23
Holiday Inn Express Lexington East - Winchester by IHG

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,933 reviews)
  • cleanliness
    Dive into summer splendour at this seasonal outdoor pool with mountain views and natural surroundings.
The price is CA $173
CA $191 total
includes taxes & fees
Jul 19 - Jul 20
Natural Bridge State Resort Park

Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa
4.5 star property
Lexington
8.4 out of 10, Very good, (707 reviews)
  • cleanliness
    Float in luxury between two pools at this golf resort with poolside cabanas and bar service.
The price is CA $146
CA $198 total
includes taxes & fees
Jun 23 - Jun 24
Marriott Lexington Griffin Gate Golf Resort & Spa

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY
3.0 star property
Georgetown
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Make a splash at this hotel's indoor pool paradise with hot tub for total relaxation.
The price is CA $103
CA $113 total
includes taxes & fees
Jul 19 - Jul 20
Country Inn & Suites by Radisson, Georgetown, KY

Comfort Suites Richmond

Comfort Suites Richmond
2.5 star property
Richmond
7.4 out of 10, Good, (760 reviews)
  • cleanliness
    Splash into a refreshing getaway at this Richmond hotel with an indoor pool, fitness centre, and complimentary breakfast buffet.
The price is CA $70
CA $77 total
includes taxes & fees
Jul 20 - Jul 21
Comfort Suites Richmond

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (760 reviews)
  • cleanliness
    Soothing indoor pool oasis for relaxation awaits at this hotel with a steamy hot tub retreat.
The price is CA $150
CA $165 total
includes taxes & fees
Jul 20 - Jul 21
Comfort Inn & Suites Mount Sterling

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
8.8 out of 10, Excellent, (1,168 reviews)
  • cleanliness
    Splash into relaxation at the indoor pool oasis, where sun loungers invite a day of rejuvenating lounging.
The price is CA $128
CA $149 total
includes taxes & fees
Jul 15 - Jul 16
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
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.

Choose what matters most at hotels with a pool in Winchester

Top Winchester Hotel Reviews

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 $77 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.
How can I save on a hotel in Winchester with Expedia?
Before booking your Winchester hotel, remember to join Expedia's free travel rewards program—One Key™. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
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.

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