Deals on vacations and trips to Winchester
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Winchester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Springfield
Price was $423, price is now $409 per person
$409
per person
Feb 5 - Feb 8
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Staff at the 24-hour front desk can provide around-the-clock assistance.
Hampton Inn Lebanon
Price was $495, price is now $444 per person
$444
per person
Feb 5 - Feb 8
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, express check-in, and express check-out are also offered.
Wildflower Ranch Inn
Price was $567, price is now $521 per person
$521
per person
Feb 5 - Feb 8
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this bed & breakfast. Guests will appreciate free perks like full breakfast and WiFi in public areas. A terrace, a garden, and a snack bar/deli are also on offer.
Hill House B&B
Price was $571, price is now $538 per person
$538
per person
Feb 5 - Feb 8
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
This bed & breakfast features free WiFi in public areas, barbecue grills, and free self parking. Enjoy the free full breakfast each morning. A terrace, a communal living room, and a picnic area are also on offer.
Top Winchester hotels deals
Best Western Winchester Hotel
1307 W Lexington Ave, Winchester, KY
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $89 total per night
$89 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A seasonal outdoor pool and a computer station are also provided.
Pool
Breakfast included
Motel 6 Lexington, KY - Airport
750 Newtown Court, Lexington, KY
Free Cancellation
$51 nightly
The price is $60 total per night
$60 total
Nov 18 - Nov 19
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli and laundry facilities are also provided.
Pet friendly
Parking included
Hilton Lexington/Downtown
369 West Vine Street, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $142 total per night
$142 total
Nov 30 - Dec 1
Total with taxes and fees
This hotel features 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the express check-out, laundry service, and free airport shuttle. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.
Pool
Free airport shuttle
GLō Best Western Lexington
1935 Stanton Way, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $109 total per night
$109 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a snack bar/deli, and express check-out are also on offer.
Pool
Breakfast included
GuestHouse Lexington
2261 Elkhorn Road, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
$65 nightly
The price is $75 total per night
$75 total
Nov 30 - Dec 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Express check-in, express check-out, and a computer station are also on offer.
Breakfast included
Parking included
Hyatt Regency Lexington
401 W High St, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $146 total per night
$146 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.
Pool
Free airport shuttle
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.
Popular places to visit
Kentucky Horse Park
4.5/5(328 reviews)
Kentucky Horse Park is a favorite place to visit in Lexington and nearby activities include horseback riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.
University of Kentucky
4.5/5(384 reviews)
Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Fayette Mall
4.5/5(321 reviews)
You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.
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