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Osborne Bend Trail Vacation Packages

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Osborne Bend Trail Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Clarion Hotel Conference Center - North

Clarion Hotel Conference Center - North

3 out of 5
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this 3-star family-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rupp Arena and Kentucky Horse Park are located nearby.
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this 4-star business-friendly hotel in Lexington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions The Red Mile Racetrack and Kroger Field are located nearby.
The Manchester

The Manchester

4 out of 5
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this 4-star hotel in Lexington. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Rupp Arena and The Red Mile Racetrack are located nearby.
Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this 3-star business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kroger Field and The Red Mile Racetrack are located nearby.
Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
per person
May 22 - May 27
found 4 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this 3-star business-friendly hotel in Frankfort. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Buffalo Trace Distillery and Old State Capitol are located nearby.
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this 3.5-star business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rupp Arena and The Red Mile Racetrack are located nearby.
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this hotel in Lexington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Kroger Field and Rupp Arena are located nearby.
The Delegate

The Delegate

3.5 out of 5
per person
May 22 - May 27
found 4 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this 3.5-star business-friendly hotel in Frankfort. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Buffalo Trace Distillery and Old Governor’s Mansion are located nearby.
The St. Clair

The St. Clair

2 out of 5
per person
May 22 - May 27
found 4 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this hotel in Frankfort. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Buffalo Trace Distillery and The Grand Theatre are located nearby.
Holiday Inn Express & Suites Lexington W - Versailles by IHG

Holiday Inn Express & Suites Lexington W - Versailles by IHG

2.5 out of 5
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Book a stay at this business-friendly hotel in Versailles. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Keeneland Racing Course and Raintree Gallery and Framing are located nearby.
Hampton Inn Lexington South-Keeneland/Airport

Hampton Inn Lexington South-Keeneland/Airport

2.5 out of 5
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions The Red Mile Racetrack and Kroger Field are located nearby.
Home2 Suites Lexington Keeneland Airport, KY

Home2 Suites Lexington Keeneland Airport, KY

3 out of 5
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this 3-star hotel in Lexington. Enjoy free breakfast, free parking, and a 24-hour fitness center. Popular attractions The Red Mile Racetrack and Kroger Field are located nearby.

5-7 Night Vacations in Osborne Bend Trail

Price found within the past 48 hours. Click for updated prices.
Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
per person
May 22 - May 27
found 4 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
The Manchester

The Manchester

4 out of 5
Distillery District
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
Zandale
per person
May 14 - May 19
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)

Osborne Bend Trail Last Minute Hotel Deals

Natural Bridge State Resort Park
Natural Bridge State Resort Park
3.5 out of 5
2135 Natural Bridge Road, Slade, KY
Stay at this 3.5-star cabin in Slade. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our ...
Natural Bridge State Resort Park
Black Bear Lodge Motel
Black Bear Lodge Motel
2.5 out of 5
781 Natural Bridge Rd, Slade, KY
Stay at this motel in Slade. Enjoy free parking, a picnic area, and satellite TV channels. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Black Bear Lodge Motel
See all 601 properties in Osborne Bend Trail
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.