Chesapeake Bay Adventure Vacations

Book a Adventure Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to ¥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Adventure vacation packages in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
The Westin Crystal City Reagan National Airport
The Royal Sonesta Washington DC Dupont Circle
Crystal Gateway Marriott
The Royal Sonesta Harbor Court Baltimore
Marriott Marquis Washington, DC
Don't see what you're looking for?
See all available trips from Chicago to Chesapeake Bay
View all trips

3 Night Adventure vacations in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
The Westin Crystal City Reagan National Airport
Crystal Gateway Marriott
Don't see what you're looking for?
See all available trips from Chicago to Chesapeake Bay
View all trips

4 Night Adventure vacations in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
American Inn Of Bethesda
Omni Shoreham Hotel
State Plaza Hotel
Don't see what you're looking for?
See all available trips from Tokyo to Chesapeake Bay
View all trips

Top Adventure Chesapeake Bay Hotels

Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd, Williamsburg, VA
  • 19 min drive from Busch Gardens Williamsburg
Stay at this 3.5-star golf resort in Williamsburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in ...
9/10 Wonderful! (3,016 reviews)
"I loved the security, cleanliness, pool, deck ,full kitchen, skyline, and comfortable beds!"

Reviewed on Sep 9, 2025

Hilton Vacation Club The Historic Powhatan Williamsburg
Hilton Vacation Club Greensprings Williamsburg

Hilton Vacation Club Greensprings Williamsburg

3 out of 5
3500 Ludwell Pkwy, Williamsburg, VA
  • 23 min drive from Busch Gardens Williamsburg
Stay at this 3-star golf resort in Williamsburg. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,007 reviews)
Home away from Home
"Family-friendly and gives a home away from home vibe. Front desk were friendly and willing to help whenever needed. Room/Bathrooms were nice and clean.😊"

Reviewed on Sep 9, 2025

Hilton Vacation Club Greensprings Williamsburg
The Royal Sonesta Harbor Court Baltimore

The Royal Sonesta Harbor Court Baltimore

4.5 out of 5
550 Light Street, Baltimore, MD
  • 6 hours drive from Busch Gardens Williamsburg
Stay at this 4.5-star luxury hotel in Baltimore. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,588 reviews)
"Had a great stay. Good location, friendly and helpful staff, clean and spacious rooms! Will be returning!"

Reviewed on Sep 7, 2025

The Royal Sonesta Harbor Court Baltimore
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.