Chesapeake Bay Vacation Packages

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Top Chesapeake Bay Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
per person
Jul. 15 - Jul. 18
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,002 reviews)
Great facility with great amenities.

Reviewed on Jun. 3, 2024

Graduate Richmond

Graduate Richmond

4 out of 5
Downtown Richmond
per person
Jul. 15 - Jul. 18
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.4/10 Very Good! (1,127 reviews)
We enjoyed the “collegiate” theme in the hotel. Noticed quite a few small maintenance details that needed to be taken care of- areas on the baseboard in our room that had been patched but not painted; towel hook on the bathroom door broken; fridge not working well (didn’t keep drinks cold). The toilet in one of our companions’ rooms had leaked overnight (from the tank, so clean water), running out of the bathroom and soaking the carpet. We informed the front desk in the morning; however, upon returning to the hotel around 4:30, the carpet was still soaked and the towels our companions had used to wipe some of the water were still on the floor. It was evident the room had not been serviced by maintenance or housekeeping. Informed the front desk and requested a room change, but the attendant stated they’d have to verify the issue work maintenance. Eventually (after much heated discussion), a supervisor became involved and provided a new room. Valet staff were friendly and efficient. The rooftop bar had no food service on Friday evening (around 6/7pm), so out want an option to get snacks with our drinks. Not sure our experience was worth what we paid.

Reviewed on Jun. 2, 2024

Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

2.5 out of 5
Short Pump
per person
Jul. 15 - Jul. 18
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.4/10 Very Good! (1,660 reviews)
Staff was friendly and helpful.

Reviewed on Jun. 3, 2024

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
per person
Jul. 15 - Jul. 18
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
9.2/10 Wonderful! (1,004 reviews)
Very nice hotel, helpful and friendly staff-especially Annabelle, the lobby cat. Wonderful breakfast at Parterre in the courtyard. Comfortable beds and spacious rooms.

Reviewed on Jun. 3, 2024

Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
per person
Jul. 15 - Jul. 18
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,004 reviews)
Met all of our needs. Only issue was finding where the washer and dryer were hidden. (We were the first floor unit, they were accessed on the second floor) 2 unit buildings.

Reviewed on Jun. 5, 2024

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.

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 hotel + flight trips in Downtown Washington D.C.

Chesapeake Bay Hotel Deals

Washington Plaza Hotel
Washington Plaza Hotel
4 out of 5
10 Thomas Circle NW, Washington, DC
The price is CA $163 per night from Jun. 30 to Jul. 1
CA $163
CA $189 total
includes taxes & fees
Jun 30 - Jul 1
8.6/10 Excellent! (3,328 reviews)
"Over all my experience in Washington DC was exceptional loved it the hotel was very convenient in all was loved it"

Reviewed on Jun. 3, 2024

Washington Plaza Hotel
State Plaza Hotel
State Plaza Hotel
3.5 out of 5
2116 E Street NW, Washington, DC
The price is CA $163 per night from Jul. 6 to Jul. 7
CA $163
CA $189 total
includes taxes & fees
Jul 6 - Jul 7
9/10 Wonderful! (1,702 reviews)
Convenient and great location
"Very welcoming and helpful staff. We appreciated gss as bingo a kitchenette. The rooms were quiet and comfortable. Good & safe location next to GWU. Very walkable to the Mall, monuments. Close to the metro station and buses."

Reviewed on Jun. 5, 2024

State Plaza Hotel
Omni Shoreham Hotel
Omni Shoreham Hotel
4 out of 5
2500 Calvert St Nw, Washington, DC
The price is CA $196 per night from Jul. 1 to Jul. 2
CA $196
CA $228 total
includes taxes & fees
Jul 1 - Jul 2
8.6/10 Excellent! (1,358 reviews)
"We have stayed here before as the Omni is located near family who live in the area. The facility and staff are consistently excellent. We had one small issue in the bathroom which was quickly addressed to our satisfaction. We will stay here again."

Reviewed on Jun. 4, 2024

Omni Shoreham Hotel
See all 14,138 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.

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Frequently asked questions

How much does a Chesapeake Bay vacation package cost?
Tailor make your Chesapeake Bay package from an affordable CA $592. 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.

Discover the most popular places to visit in Chesapeake Bay

Image for 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
Image for 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
Image for National Mall

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

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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.