Find Hotels with an Outdoor Pool in Winchester, KY

Discover top Winchester attractions

Winchester, Kentucky, offers a serene retreat for travelers seeking relaxation, particularly with its inviting hotels featuring pools. Begin your journey at the beautiful Fort Boonesborough State Park, where you can enjoy a leisurely picnic by the river or immerse yourself in the rich history of the early settlers. Next, explore the tranquil waters of the Kentucky River, perfect for a scenic boat ride or a relaxing afternoon of fishing. The serene landscapes of the Bluegrass Region provide an ideal backdrop for a quiet hike or a bike ride along the scenic trails. Wine enthusiasts will appreciate a visit to the nearby Chrisman Mill Vineyard, where you can sample local wines while taking in the peaceful vineyard views. Finally, the Winchester Golf Club offers a leisurely day on the greens for those looking to unwind in a beautiful outdoor setting. For accommodations, consider staying in the heart of Winchester, where you can find hotels with pools that promise a refreshing break after your daily adventures, along with attentive service that caters to your every need, ensuring a pampered experience during your stay.

Find the best hotels with an outdoor pool in Winchester

For travelers seeking a refreshing escape in Winchester, Kentucky, these hotels feature inviting outdoor pools that promise relaxation and enjoyment during your stay.

Hampton Inn Winchester

• Why it's great for poolside lounging: With an impressive review rating of 8.8, Hampton Inn Winchester is ideal for guests who want to relax by the pool under the Kentucky sun. The hotel features a lovely outdoor pool, providing a perfect spot for leisure and recreation for travelers of all ages.
• Other amenities: Guests enjoy complimentary breakfast, including a buffet option, and conveniences such as air conditioning and daily housekeeping. The hotel also offers fitness facilities for those looking to stay active. With self-parking available and easy access to the historical district, this hotel combines comfort with a great location for outdoor exploration.
• Nearby attractions: The Holler - 1.17 miles, Lykins Park - 1.18 miles, Bluegrass Heritage Museum - 1.76 miles

Best Western Winchester Hotel

• Why it's great for poolside lounging: The Best Western Winchester Hotel is a great choice for travelers looking for a comfortable stay with an inviting pool experience. This hotel boasts a solid review rating of 8.4 and has a welcoming atmosphere. Guests can enjoy a refreshing dip in the pool, perfect for unwinding after a day of exploring the area.
• Other amenities: In addition to the pool, the hotel features free breakfast options, including a full breakfast daily, and convenient in-room amenities such as a kitchenette, refrigerator, and microwave. Guests also appreciate the daily housekeeping service and self-parking options. For those looking to explore, nearby golf courses are a short drive away, adding to the outdoor adventure opportunities.

Baymont by Wyndham Winchester

• Why it's great for poolside lounging: The Baymont by Wyndham Winchester offers a pleasant retreat with a review rating of 7.4, featuring both indoor and outdoor pools for guests to enjoy. This hotel is perfect for travelers seeking a fun and relaxing atmosphere, where they can take a refreshing swim during their stay.
• Other amenities: Guests can start their day with a complimentary breakfast and take advantage of in-room amenities such as microwaves and air conditioning. The hotel also provides fitness facilities and daily housekeeping services. With free self-parking and a pet-friendly policy, it accommodates various traveler needs, ensuring a comfortable visit.
• Nearby attractions: The Holler - 1.27 miles, Lykins Park - 1.17 miles, Bluegrass Heritage Museum - 1.87 miles