Chesapeake Bay Vacation Packages

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Your Chesapeake Bay Vacation

Set off on a thrilling adventure with a vacation package to Chesapeake Bay. This destination's history are just one of the things that make this place a visitor favourite. Kick off your trip to Chesapeake Bay with a couple of days in Washington visiting popular attractions like National Mall and White House. Baltimore is another top city that draws crowds from near and far. National Aquarium in Baltimore and Oriole Park at Camden Yards are two of the top places to see in this destination. When it's time to stop dreaming and start discovering, Expedia will help turn your Chesapeake Bay vacation into a reality.

Top Chesapeake Bay Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
per person
Aug 31 - Sep 6
just found
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
9/10 Wonderful! (1,010 reviews)
This is a great family resort! The rooms are updated and clean. The staff is nice and the grounds are kept. The price is reasonable. The best part is the pool. It's hours of fun for the kids and clean! There is something for everyone.

Reviewed on Jul. 13, 2025

Barsala At Sphere Apartments

Barsala At Sphere Apartments

3.5 out of 5
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.6/10 Excellent! (14 reviews)
Overall this property was a good place to stay so we could spread out and have extra room for our trip. Communication was fine and checkin instructions were very detailed. I cannot give it 5 stars however. The shower curtain and shower were dirty. There were stains on the bed linens and the comforter as well as a hole in the comforter. The property also charges $5/day for parking which was not disclosed in the original price. The exterior of the property had a dog area and people did not clean up after their dog — this was also the area we were required to park.

Reviewed on Jun. 29, 2025

Warner Hall

Warner Hall

3 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
10/10 Exceptional! (9 reviews)
We had a wonderful, relaxing weekend stay at Warner Hall. The hosts Christina and Fred were very welcoming and the house and property is amazing. The house (more like mansion) and rooms are huge and comfortable with lots of space for reading a book, etc. We really enjoyed the morning coffee and tea service brought straight to our rooms. We felt like royalty! There's so much history to the Warners, we had no idea. Definitely highly recommend this place if you're looking for a break from being busy busy.

Reviewed on Jul. 9, 2025

Hilton Garden Inn Richmond South/Southpark

Hilton Garden Inn Richmond South/Southpark

3 out of 5
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.6/10 Excellent! (884 reviews)
Beautiful hotel! Staff is very friendly, and great location.

Reviewed on Jun. 24, 2025

DoubleTree by Hilton Richmond - Midlothian

DoubleTree by Hilton Richmond - Midlothian

4 out of 5
North Chesterfield
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8/10 Very Good! (1,003 reviews)
The staff was so rude, and didn’t even bother to help and when I even did get help it was like a bother to them so much and giving us such looks as if we aren’t people, I felt very judged within this hotel and did not like any of the staff, I didn’t even cause a problem, but I do love the room and where it’s located over all 3/5 stars

Reviewed on Jul. 12, 2025

Where to stay in Chesapeake Bay

Find the best Chesapeake Bay areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake Bay
Downtown Washington D.C. showing street scenes, a city and night scenes

Downtown Washington D.C.

1 out of top 10 points of interest in this area
4.5/5(269 area reviews)

Central business district boasting Penn Quarter, Chinatown, and CityCenterDC, with a variety of bars, restaurants, and theaters. Explore historic sites like Lafayette Square and enjoy diverse dining options such as Fogo de Chão and Old Ebbitt Grill.

Find hotels in Downtown Washington D.C.

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Chesapeake Bay Hotel Deals

Washington Plaza Hotel

Washington Plaza Hotel

4 out of 5
10 Thomas Circle NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Jul 20 to Jul 21
CA $149
CA $173 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (4,478 reviews)
"Wonderful staff! Cleanliness is on point! Loved the entire stay!"

Reviewed on Jul. 15, 2025

Washington Plaza Hotel
Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
2500 Calvert St Nw, Washington, DC
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Aug 8 to Aug 9
CA $144
CA $207 total
Aug 8 - Aug 9
includes taxes & fees
8.6/10 Excellent! (1,983 reviews)
"Loved the pool"

Reviewed on Jul. 11, 2025

Omni Shoreham Hotel
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
1001 14th St NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Aug 15 to Aug 16
CA $148
CA $213 total
Aug 15 - Aug 16
includes taxes & fees
8.6/10 Excellent! (2,488 reviews)
"We really enjoyed the location of this hotel, it was walkable and Lyft was used when necessary!"

Reviewed on Jul. 14, 2025

Hamilton Hotel Washington DC
See all 14,975 properties in Chesapeake Bay
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Chesapeake Bay

National Mall featuring a city, an administrative building and heritage architecture

National Mall

4.5/5(198 reviews)

Inspiring architecture, magnificent museums and the icons of American history await on Washington’s famous two-mile (three-kilometer) strip.

National Mall
Busch Gardens Williamsburg

Busch Gardens Williamsburg

5/5(3 reviews)

Enjoy the excitement at Busch Gardens Williamsburg and see why people love this amusement park in Williamsburg. Experience the entertainment choices or attend a sporting event in this family-friendly area.

Busch Gardens Williamsburg
White House

White House

4/5(388 reviews)

Explore the home and workplace of the president of the United States. See entertainment areas and state rooms and learn about the history of this famous building.

White House

What to do in Chesapeake Bay

Food Tour Plate

Historic Annapolis Food Tour

CA $110
per adult
Historic Annapolis Food Tour
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

CA $13
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Annapolis: Ghosts of the Harbor & Old Town Tour

Annapolis: Ghosts of the Harbor & Old Town Tour

CA $37
per adult
Annapolis: Ghosts of the Harbor & Old Town Tour
See all activities in Chesapeake Bay

Frequently asked questions

How much does a Chesapeake Bay vacation package cost?
Tailor make your Chesapeake Bay package from an affordable CA $919. Choose from any combination of hotels, flights and rental cars to build the trip of your dreams. Don't forget to add on some tours and experiences!
How do I get a cheap travel package to Chesapeake Bay?
Crafting your own Chesapeake Bay vacation package with Expedia is a smart way to save. We have access to more than 550 airlines and 1,000,000 properties around the world. With such an awesome range to pick from, you'll have no hassles putting together your dream escape.
Where should I stay in Chesapeake Bay?
To explore well-known attractions such as White House and Washington Monument, Washington is the place to be. Lots of travelers also adore Baltimore, home to National Aquarium in Baltimore and Oriole Park at Camden Yards. If time is on your side, why not visit both cities?
What are the top hotels in Chesapeake Bay?
For hotels in Ocean City with comfy beds and friendly service, you can't go past Wingate by Wyndham Baltimore BWI Airport and Renaissance Baltimore Harborplace Hotel. If you're visiting Washington as well, you'll get a solid night's sleep at Luxor Hotel and Casino or Circus Circus Hotel, Casino & Theme Park.
How far in advance should I book my Chesapeake Bay vacation?
Smart travelers often book early. You can normally start comparing international fares on Expedia up to 12 months before your intended flight. If you're purchasing tickets last minute, there's no need to worry. Budget prices occasionally appear just weeks prior to departure.
What does an Expedia Chesapeake Bay travel package include?
Rental cars, flights and hotels, or any combination of the three --- it's totally up to you. Whether you're headed to Chesapeake Bay with the family or adventuring solo, there's a bundle to suit every style and budget. Once you've made your booking, why not add on some tours as well?
What should I know before booking a Chesapeake Bay travel package?
You can save big by bundling your hotels, flights and rental cars. Once you've made your booking, you can add on things like activities or tours. Your next unforgettable adventure is only a few clicks away.
Can I choose my airline with a Chesapeake Bay Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Just choose the airline you want and craft the perfect Chesapeake Bay vacation.
If I'm not able to travel, can I cancel my Chesapeake Bay vacation package?
You can. We get that even the best-laid plans can go awry, so we're happy to help if you need to make changes to your Chesapeake Bay vacation package. It may be possible to change or cancel your itinerary at no cost if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.