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

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Check availability on Winchester Hotels with a Pool

Tonight
13 Aug - 14 Aug
Tomorrow
14 Aug - 15 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for Winchester hotels with a pool

Seasonal outdoor pool
Reception
Snack bar
Room, 1 King Bed, Accessible | Select Comfort beds, in-room safe, desk, laptop workspace

1. Hampton Inn Winchester

Hampton Inn Winchester
Winchester
  • Seasonal outdoor pool creates refreshing summer sanctuary at this hotel, offering a peaceful retreat in the heart of Winchester.
SAR 366
SAR 404 total
includes taxes & fees
23 Aug - 24 Aug
Hampton Inn Winchester
Indoor pool
Exterior
Exterior
Standard Room, 2 Queen Beds, Accessible Bathtub (Accessible Tub) | In-room safe, desk, laptop workspace, blackout drapes

2. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
Winchester
  • Dive into aquatic bliss in this rural retreat with an indoor pool open from dawn to dusk.
SAR 413
SAR 455 total
includes taxes & fees
10 Sep - 11 Sep
Holiday Inn Express Lexington East - Winchester by IHG
Seasonal outdoor pool
Free daily full breakfast
Standard Room, 2 Double Beds, Non Smoking, Kitchenette | Desk, iron/ironing board, rollaway beds (surcharge), bed sheets
Standard Room, 2 Double Beds, Non Smoking, Kitchenette | Bathroom | Combined shower/tub, hair dryer, towels

3. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
  • Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.
SAR 321
SAR 354 total
includes taxes & fees
18 Aug - 19 Aug
Best Western Winchester Hotel
Indoor pool
Lobby
Suite, 2 Queen Beds | Desk, laptop workspace, iron/ironing board, WiFi (free)
Free daily continental breakfast

4. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
Winchester
  • Refreshing year-round aquatic escape awaits at this Winchester hotel's indoor pool, complemented by a modern fitness center.
SAR 284
SAR 313 total
includes taxes & fees
16 Aug - 17 Aug
Baymont by Wyndham Winchester
Indoor pool, sun loungers
Exterior
Deluxe Room, 1 King Bed, Accessible, Non Smoking (Mobility/Hearing Impaired Accessible) | Premium bedding, pillowtop beds, desk, blackout drapes
Lobby

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

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Lexington
  • Splash into relaxation at the indoor pool oasis, where sun loungers invite a day of rejuvenating lounging.
SAR 324
SAR 376 total
includes taxes & fees
16 Aug - 17 Aug
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Indoor pool
One Queen Bed, Non-Smoking | In-room safe, desk, iron/ironing board, WiFi (free)
In-room safe, desk, iron/ironing board, WiFi (free)
In-room safe, desk, iron/ironing board, WiFi (free)

6. Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area
Lexington
  • Splash into comfort at this Lexington hotel with an indoor pool open from 7 AM to 11 PM daily.
SAR 320
SAR 372 total
includes taxes & fees
8 Sep - 9 Sep
Hampton Inn I-75 Lexington/Hamburg Area
Indoor pool
Exterior
Lobby
Restaurant

7. Hyatt Place Lexington

Hyatt Place Lexington
Lexington
  • Tranquil indoor pool sanctuary awaits with rejuvenating waters to complement your stay at this perfectly located Lexington hotel.
SAR 379
SAR 440 total
includes taxes & fees
19 Aug - 20 Aug
Hyatt Place Lexington
Indoor pool
Bar (on property)
Reception
Lobby sitting area

8. Hotel Lex and Conference Center, Trademark Collection

Hotel Lex and Conference Center, Trademark Collection
Lexington
  • Dive into indoor pool bliss at this Lexington hotel where family fun and fitness unite.
SAR 294
SAR 341 total
includes taxes & fees
19 Aug - 20 Aug
Hotel Lex and Conference Center, Trademark Collection
Indoor pool
Meeting facility
Daily cooked-to-order breakfast for a fee
Bar (on property)

9. Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
Lexington
  • Dive into a luxurious indoor pool sanctuary at this Hamburg hotel, complete with a poolside firepit and relaxing terrace.
SAR 375
SAR 436 total
includes taxes & fees
13 Sep - 14 Sep
Holiday Inn Lexington - Hamburg by IHG
Indoor pool
Front of property - evening/night
Lobby sitting area
Free daily continental breakfast

10. Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg
Lexington
  • Refreshing swims await at this Lexington hotel's indoor pool, with convenient access to local attractions and premium amenities.
SAR 243
SAR 282 total
includes taxes & fees
13 Sep - 14 Sep
Spark by Hilton Lexington Hamburg
View all properties

Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Winchester Hotel Reviews

Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"Friendly people in a beautiful area! The views are amazing! The lodge is not too big, and not too small... and the architecture blends in nicely with the scenery. Our balcony was nice and deep! It was great to still be able to safely enjoy that sheltered sense of being up in the woods and watch as a summer rainstorm passed through the area. "
Terry L 1-night trip
Posted less than an hour ago
Natural Bridge State Resort Park
Hyatt Place Lexington

Hyatt Place Lexington

8/10 Good
"Clean, convenient near I75 and Costco (gas)."
Andrei 1-night trip
Posted 1 day ago
Hyatt Place Lexington
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

8/10 Good
"Clean and friendly but a few small issues. safe broken in the room and window blinds broken - repaired with velcro"
Gail 1-night trip
Posted 2 days ago
Embassy Suites by Hilton Lexington Green

Frequently asked questions

What are some accommodations with pools in Winchester?
Baymont by Wyndham Winchester: Features daily, a pool, and free self parking. Best Western Winchester Hotel: Offers full, a seasonal outdoor pool, and free self parking.
What is there to see and do in Winchester?
Spend some time experiencing the great outdoors at College Park and GRCHS Baseball Field. During your stay, check out sights such as Bluegrass Heritage Museum, Winchester Opera House, and Clark County Courthouse. You'll also discover lots of options for restaurants in Winchester.
When is the best time to book a hotel with a pool in Winchester?
You may want to consider a place to stay that offers an outdoor pool if you plan to visit Winchester in the hottest months of July, August, or June when the average temp is 72°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 38°F.