Package deals near Port of Leonardtown Winery

Save more on your trip when booking your flight + hotel together

Top Port of Leonardtown Winery vacation deals

Price found within the past 48 hours. Click for updated prices.
Residence Inn Washington Capitol Hill/Navy Yard
3.0-star property

Residence Inn Washington Capitol Hill/Navy Yard

Navy Yard
9.2/10 Wonderful! (1,005 reviews)

Jan 29 - Feb 1

3 night stay

Chicago (CHI) to Washington (DCA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $327, price is now $225 per person
$225
per person
found 1 day ago
Beautiful! Perfect for my family

Reviewed on Aug 26, 2025

Salamander Washington DC
5.0-star property

Salamander Washington DC

Southwest
18.8/10 Exceptional! (1,019 reviews)

Jan 29 - Feb 1

3 night stay

Chicago (CHI) to Washington (DCA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $729, price is now $466 per person
$466
per person
found 1 day ago
The staff go out the way to accommodate every want or need.

Reviewed on Aug 21, 2025

Hilton McLean Tysons Corner
4.0-star property

Hilton McLean Tysons Corner

8.6/10 Excellent! (1,005 reviews)

Dec 16 - Dec 22

6 night stay

Chicago (ORD) to Washington (DCA)

United • Coach

Washington (DCA) to Chicago (ORD)

Frontier Airlines • Coach
Save 100% on your flight
Price was $837, price is now $576 per person
$576
per person
found 7 hours ago
Loved staying at this hotel. Very convenient- best local shuttle service I’ve ever experienced. Enjoyed having a Peloton in my room.

Reviewed on Sep 29, 2024

Omni Shoreham Hotel
4.0-star property

Omni Shoreham Hotel

Northwest
17.6/10 Exceptional! (2,186 reviews)

Jan 29 - Feb 1

3 night stay

Chicago (CHI) to Washington (DCA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $386, price is now $267 per person
$267
per person
found 1 day ago
Friendly and welcoming front desk staff

Reviewed on Sep 5, 2025

Hotel Belvoir Springfield
3.5-star property

Hotel Belvoir Springfield

16.8/10 Exceptional! (1,001 reviews)

Dec 16 - Dec 22

6 night stay

Chicago (ORD) to Washington (DCA)

United • Coach

Washington (DCA) to Chicago (ORD)

Frontier Airlines • Coach
Save 100% on your flight
Price was $552, price is now $383 per person
$383
per person
found 7 hours ago
Clean inside but property is rundown, small lobby. Staff very helpful

Reviewed on Apr 19, 2025

Fairmont Washington, D.C., Georgetown
4.0-star property

Fairmont Washington, D.C., Georgetown

Northwest
9.4/10 Exceptional! (1,003 reviews)

Jan 16 - Jan 19

3 night stay

Chicago (MDW) to Washington (DCA)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $704, price is now $490 per person
$490
per person
found 1 day ago
Restaurant kitchen: pour menu.

Reviewed on Aug 5, 2024

Hotel deals near Port of Leonardtown Winery

The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel

2.5 out of 5
41655 Park Avenue, Leonardtown, MD
Free Cancellation
1.51 mi from Port of Leonardtown Winery
$130 nightly
The price is $145 total per night
$145 total
Dec 7 - Dec 8
Total with taxes and fees
The Inn at Leonardtown, an Ascend Collection Hotel features free WiFi in public areas and a banquet hall. There's free parking if you drive. The front desk is staffed 24/7 to help with luggage storage, and answer any questions about the accommodations.
Parking included
Free WiFi
Spark by Hilton California Lexington Park

Spark by Hilton California Lexington Park

2.5 out of 5
44941 Worth Ave, California, MD
Free Cancellation
Reserve now, pay when you stay
7.31 mi from Port of Leonardtown Winery
$103 nightly
The price is $115 total per night
$115 total
Nov 30 - Dec 1
Total with taxes and fees
At Spark by Hilton California Lexington Park, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. You can take advantage of free parking if you drive. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, securing valuables, and luggage storage. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
Sleep Inn & Suites California MD

Sleep Inn & Suites California MD

2.5 out of 5
23428 Three Notch Rd, California, MD
Free Cancellation
6.76 mi from Port of Leonardtown Winery
$109 nightly
The price is $121 total per night
$121 total
Nov 24 - Nov 25
Total with taxes and fees
Sleep Inn & Suites California MD features a gym, free WiFi in public areas, and a 24-hour business center. A stay here includes free parking. The 24-hour front desk has staff standing by to help with dry cleaning or laundry, and answer any questions about the accommodations. Additional amenities include laundry facilities and a vending machine.
Breakfast included
Parking included
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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.

Book a Port of Leonardtown Winery vacation package

Stop dreaming and start traveling. If you’ve always wanted to see Port of Leonardtown Winery, now is the perfect time. Book your getaway to Leonardtown with Orbitz and get ready to tick this attraction off your bucket list. Plus when you lock in your package with us, you’ll have plenty of cash leftover to splash out on other amazing Leonardtown sights. Because travel is all about investing in experiences, not things!

If you’re hoping to stay close to Port of Leonardtown Winery, we’ve got you covered. Choose from a great range of hotels not far from this attraction. Roll out of bed, slip on your walking shoes and you’ll be there within moments. What could be more convenient than that? You won’t just be close to all the action — you’ll save money on transportation, and a hot shower and cozy bed will be within reach after a big day of exploring. Now that’s what we call a stress- free, full-of-fun getaway.

Orbitz has your ticket to a rewarding Port of Leonardtown Winery vacation. Book your Leonardtown package with us and you’ll be able to access Orbitz Rewards. Earn Orbucks when you reserve your flights, hotels and activities with Orbitz and redeem them at over 385,000 hotels worldwide. $1 Orbuck = $1 off your next hotel. Join, earn, redeem — just like that! When you join Orbitz Rewards, you’ll also instantly unlock exclusive deals and save on thousands of properties with Insider Pricing.

We believe the best reward that you can give to yourself or others is the gift of travel. So, don’t put off exploring Port of Leonardtown Winery any longer. Save a bundle and book your Leonardtown escape with Orbitz today.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.