Chesapeake Bay All inclusive Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to NZ$616 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top All inclusive Chesapeake Bay Hotels
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd, Williamsburg, VA
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 ...
8.8/10 Excellent! (2,917 reviews)
"Breakfast outstanding Beds was so comfortable"
Reviewed on 4 Aug. 2025
Embassy Suites by Hilton Washington DC Georgetown
1250 22nd St NW, Washington, DC
Book a stay at this family-friendly hotel in Washington. Enjoy free breakfast, room service, and a 24-hour health club. Our guests praise the breakfast and the ...
8.8/10 Excellent! (1,003 reviews)
"Free breakfast included a made-to-order omelet station! Beds were suitable, but not luxurious. Really appreciated the complementary daily drinks and grab and go."
Reviewed on 5 Aug. 2025
Great Wolf Lodge Williamsburg
549 East Rochambeau Drive, Williamsburg, VA
Stay at this 3.5-star family-friendly resort in Williamsburg. Enjoy 5 indoor pools, 2 restaurants, and 2 hot tubs. Our guests praise the helpful staff in our ...
8.4/10 Very Good! (1,002 reviews)
"The waterslides were very fun"
Reviewed on 28 Jul. 2025
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.