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Stamping Ground Vacation Packages

Build your package with 2 more options

Stamping Ground Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
MainStay Suites Georgetown Lexington North

MainStay Suites Georgetown Lexington North

2.5 out of 5
Price was $613, price is now $534 per person
$534
per person
Nov 18 - Nov 23
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Book a stay at this business-friendly hotel in Georgetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Toyota Visitor Center and Country Boy Brewing are located nearby.

The Delegate

The Delegate

3.5 out of 5
Price was $791, price is now $640 per person
$640
per person
Nov 18 - Nov 23
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this hotel in Frankfort. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Buffalo Trace Distillery and Old Governor’s Mansion are located nearby.
Exceptional boutique Hotel with an amazing restaurant attached in downtown Frankfurt walking distance to many restaurants the old state capital of many other things

Reviewed on Sep 4, 2026

The Ashbrook Hotel

The Ashbrook Hotel

3.5 out of 5
Price was $874, price is now $748 per person
$748
per person
Nov 18 - Nov 23
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Book a stay at this business-friendly hotel in Frankfort. Enjoy free WiFi, free parking, and meeting facilities. Popular attractions Buffalo Trace Distillery and Liberty Hall are located nearby.
Room didn’t seem clean (dirt/ hairs on window sills and below sink) or well maintained (see picture). Couldn’t regulate shower off of HOT! Bed was comfortable and room was large

Reviewed on Aug 30, 2026

Rose Hill Inn

Rose Hill Inn

4 out of 5
Price was $1,021, price is now $877 per person
$877
per person
Nov 18 - Nov 23
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this guesthouse in Versailles. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Nostalgia Station Toy Train Museum and Raintree Gallery and Framing are located nearby.
What a treasure. Rose Hill Inn is a beautiful property walkable to shopping and restaurants. The owners are delightful… so friendly and helpful. Breakfast was delicious and we had anything we needed and then some.

Reviewed on Aug 16, 2026

Hampton Inn Richmond

Hampton Inn Richmond

2.5 out of 5
Price was $859, price is now $740 per person
$740
per person
Nov 18 - Nov 23
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this hotel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Richmond Centre Mall and Cinemark At Richmond Centre are located nearby.
Everything was top tier.

Reviewed on Aug 31, 2026

Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
Price was $867, price is now $751 per person
$751
per person
Nov 18 - Nov 23
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this B&B in Versailles. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Nostalgia Station Toy Train Museum and Raintree Gallery and Framing are located nearby.
Breakfast was delicious. Loved the pet dog

Reviewed on Aug 24, 2026

Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $748, price is now $656 per person
$656
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this 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 Red Mile Racetrack and Kroger Field are located nearby.
I was pleasantly pleased with the Elwood hotel. It was very clean and decorated lovely.The rooms are large and spacious. The staff was wonderful to us and our dog Lily. There are many places to bring your dog for a walk and they even had dog bags. We will be returning there every time we go to Kentucky to visit our son in college.

Reviewed on Sep 4, 2026

Candlewood Suites Lexington by IHG

Candlewood Suites Lexington by IHG

2.5 out of 5
Price was $739, price is now $652 per person
$652
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Rupp Arena and Kroger Field are located nearby.
Great place to stay! Seemed quiet and safe

Reviewed on Sep 3, 2026

Stamping Ground Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Comfort Inn Winchester

Comfort Inn Winchester

2.5 out of 5
Price was $581, price is now $517 per person
$517
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $1,724, price is now $1,521 per person
$1,521
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
The Delegate

The Delegate

3.5 out of 5
Price was $1,051, price is now $927 per person
$927
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

3 out of 5
Price was $1,109, price is now $984 per person
$984
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)

Stamping Ground Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Delegate

The Delegate

3.5 out of 5
Price was $791, price is now $640 per person
$640
per person
Nov 18 - Nov 23
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
The Ashbrook Hotel

The Ashbrook Hotel

3.5 out of 5
Price was $874, price is now $748 per person
$748
per person
Nov 18 - Nov 23
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Rose Hill Inn

Rose Hill Inn

4 out of 5
Price was $1,021, price is now $877 per person
$877
per person
Nov 18 - Nov 23
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Hampton Inn Richmond

Hampton Inn Richmond

2.5 out of 5
Price was $859, price is now $740 per person
$740
per person
Nov 18 - Nov 23
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)

Top Flight Deals

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

American Airlines
Tue, Oct 6 - Sat, Oct 10
SAN
San Diego Intl.
LEX
Blue Grass
$271 Roundtrip, found 1 day ago
$271
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from San Diego Intl. to Blue Grass, returning Sat, Oct 10, priced at $271 found 1 day ago
Bargain Flight
Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
LEX
Blue Grass
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Sep 29 from Los Angeles Intl. to Blue Grass, returning Sat, Oct 3, priced at $297 found 1 day ago
Bargain Flight
Tue, Sep 22 - Tue, Oct 6
SEA
Seattle - Tacoma Intl.
LEX
Blue Grass
$307 Roundtrip, found 1 day ago
$307
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Sep 22 from Seattle - Tacoma Intl. to Blue Grass, returning Tue, Oct 6, priced at $307 found 1 day ago
American Airlines
Tue, Oct 13 - Tue, Oct 20
IAH
George Bush Intercontinental
LEX
Blue Grass
$323 Roundtrip, found 20 hours ago
$323
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Tue, Oct 13 from George Bush Intercontinental to Blue Grass, returning Tue, Oct 20, priced at $323 found 20 hours ago