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Winchester Vacation Packages

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Winchester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Capital O 3Y Motel Mount Vernon Renfro Valley

Capital O 3Y Motel Mount Vernon Renfro Valley

2.5 out of 5
Price was $517, price is now $459 per person
$459
per person
Dec 18 - Dec 22
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Lexington (LEX)
Stay at this hotel in Mount Vernon. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Mt. Vernon Park and Kentucky Music Hall of Fame and Museum are located nearby.

Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
Price was $735, price is now $635 per person
$635
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Lexington (LEX)
Stay at this B&B in Versailles. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The Kentucky Castle and Nostalgia Station Toy Train Museum are located nearby.

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $666, price is now $587 per person
$587
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Kroger Field and Red Mile Racetrack are located nearby.
Great location ! Always very friendly clean well maintained!

Reviewed on Nov 9, 2026

Rose Hill Inn

Rose Hill Inn

4 out of 5
Price was $793, price is now $711 per person
$711
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Lexington (LEX)
Stay at this guesthouse in Versailles. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The Kentucky Castle and Nostalgia Station Toy Train Museum are located nearby.
We stayed at Rose Hill inn for one night in the hideaway attic, and if was so cute and charming! The property is so beautiful and the home is very historic and interesting. The owners were very welcoming and the breakfast was delicious! Definitely recommend staying here.

Reviewed on Nov 9, 2026

Clarion Hotel Conference Center Lexington North

Clarion Hotel Conference Center Lexington North

3 out of 5
Price was $590, price is now $531 per person
$531
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Lexington (LEX)
Book a stay at this 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.
It was advertised as having an indoor pool, hot tub and sauna. When we got there none of them were in service. Called and asked the front desk and they said “it’s on the website that we don’t do that anymore “. Nope … it’s not . I would’ve booked somewhere nicer.

Reviewed on Nov 8, 2026

Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
Price was $670, price is now $606 per person
$606
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Lexington (LEX)
Book a stay at this luxury resort in Lexington. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Rupp Arena and Red Mile Racetrack are located nearby.
Hotel was very beautiful and staff was very accommodating. The hotel car was a big bonus!

Reviewed on Nov 10, 2026

Renfro Ridge Extended Stay and Suites

Renfro Ridge Extended Stay and Suites

2 out of 5
Price was $547, price is now $495 per person
$495
per person
Dec 18 - Dec 22
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Lexington (LEX)
Stay at this hotel in Mount Vernon. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Kentucky Music Hall of Fame and Museum and Mt. Vernon Park are located nearby.

The Aldenberg Hotel

The Aldenberg Hotel

2 out of 5
Price was $759, price is now $687 per person
$687
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Lexington (LEX)
Stay at this hotel in Versailles. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions The Kentucky Castle and Nostalgia Station Toy Train Museum are located nearby.
Staff was extremely kind. Especially loved shuttle service to Keeneland

Reviewed on Oct 19, 2026

Winchester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Capital O 3Y Motel Mount Vernon Renfro Valley

Capital O 3Y Motel Mount Vernon Renfro Valley

2.5 out of 5
Price was $517, price is now $459 per person
$459
per person
Dec 18 - Dec 22
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Lexington (LEX)
Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
Price was $735, price is now $635 per person
$635
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Lexington (LEX)
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $666, price is now $587 per person
$587
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Lexington (LEX)
Rose Hill Inn

Rose Hill Inn

4 out of 5
Price was $793, price is now $711 per person
$711
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Lexington (LEX)

Winchester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Georgetown

Super 8 by Wyndham Georgetown

2 out of 5
Price was $824, price is now $768 per person
$768
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Lexington (LEX)
Studio 6 Georgetown, KY – Lexington North

Studio 6 Georgetown, KY – Lexington North

2 out of 5
Price was $781, price is now $769 per person
$769
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Lexington (LEX)
Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

3 out of 5
Price was $837, price is now $825 per person
$825
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Lexington (LEX)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Bargain Flight
Tue, Nov 17 - Sat, Nov 21
LAX
Los Angeles Intl.
LEX
Blue Grass
$341 Roundtrip, found 1 day ago
$341
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Nov 17 from Los Angeles Intl. to Blue Grass, returning Sat, Nov 21, priced at $341 found 1 day ago
Delta
Mon, Jan 18 - Sun, Jan 24
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jan 18 from Newark Liberty Intl. Airport to Blue Grass, returning Sun, Jan 24, priced at $349 found 1 day ago
Delta
Mon, Dec 21 - Fri, Dec 25
JFK
John F. Kennedy Intl.
LEX
Blue Grass
$485 Roundtrip, found 1 hour ago
$485
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Dec 21 from John F. Kennedy Intl. to Blue Grass, returning Fri, Dec 25, priced at $485 found 1 hour ago
Delta
Sat, Dec 26 - Wed, Dec 30
LGA
LaGuardia
LEX
Blue Grass
$508 Roundtrip, found 1 day ago
$508
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Dec 26 from LaGuardia to Blue Grass, returning Wed, Dec 30, priced at $508 found 1 day ago