Chesapeake Bay Vacation Packages

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Top Chesapeake Bay Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
per person
Jun. 27 - Jun. 30
found 1 hour ago
Roundtrip non-stop flight included
Buffalo (BUF) to Richmond (RIC)
8.2/10 Very Good! (1,000 reviews)
Loved the villa and it was SO CLEAN. The staff were great. We enjoyed the pool, mini golf and playing horseshoes! It was really close to Busch Gardens and Colonial Williamsburg.

Reviewed on May 25, 2024

Greensprings Vacation Resort

Greensprings Vacation Resort

3 out of 5
per person
Jun. 27 - Jun. 30
found 1 hour ago
Roundtrip non-stop flight included
Buffalo (BUF) to Richmond (RIC)
8.4/10 Very Good! (1,003 reviews)
Very nice. I would absolutely stay here again.

Reviewed on May 26, 2024

Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
per person
Jun. 27 - Jun. 30
found 1 hour ago
Roundtrip non-stop flight included
Buffalo (BUF) to Richmond (RIC)
8.6/10 Excellent! (1,005 reviews)
Overall a wonderful stay. However, I would suggest more help at the front desk. We checked in on a Thursday night at the start of a holiday weekend. There was only one person checking everyone in, with a line from the reception desk to the front door. I applaud Demetria, who checked us in, for maintaining exemplary composure and for repeatedly expressing gratitude for everyone’s patience. Her calm and pleasant demeanor was refreshing.

Reviewed on May 25, 2024

Wedmore Place

Wedmore Place

3.5 out of 5
per person
Jun. 27 - Jun. 30
found 1 hour ago
Roundtrip non-stop flight included
Buffalo (BUF) to Richmond (RIC)
9.4/10 Exceptional! (978 reviews)
Amazing experience! Will return.

Reviewed on May 22, 2024

Club Wyndham Patriots’ Place

Club Wyndham Patriots’ Place

3 out of 5
per person
Jun. 27 - Jun. 30
found 1 hour ago
Roundtrip non-stop flight included
Buffalo (BUF) to Richmond (RIC)
8.2/10 Very Good! (712 reviews)
We had a very pleasant stay at Patriot’s Place.We really appreciated the extra space the suite offered for our pack n play and that all furniture was anchored in the walls. It was very convenient that we were not asked to wash all the dishes before check out or prep the laundry setting this property above similarly sized airbnbs. It was raining but we really wish we could have enjoyed the pool. It looked really nice!

Reviewed on May 19, 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
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from May 27 to May 28
CA $163
CA $189 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (3,279 reviews)
"Excellent"

Reviewed on May 24, 2024

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 $226 per night from Jun. 1 to Jun. 2
CA $226
CA $262 total
includes taxes & fees
Jun 1 - Jun 2
8.4/10 Very Good! (1,305 reviews)
"Easy starting point to get around city"

Reviewed on May 24, 2024

Omni Shoreham Hotel
Capital Hilton
Capital Hilton
4 out of 5
1001 16th St NW, Washington, DC
The price is CA $191 per night from Jun. 1 to Jun. 2
CA $191
CA $262 total
includes taxes & fees
Jun 1 - Jun 2
8/10 Very Good! (1,001 reviews)
"A beautiful hotel within 5 mins walk of the White House and many of the DC museums."

Reviewed on May 17, 2024

Capital Hilton
See all 14,160 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

Frequently asked questions

How much does a Chesapeake Bay vacation package cost?
Tailor make your Chesapeake Bay package from an affordable CA $745. 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 Virginia Beach Boardwalk

Virginia Beach Boardwalk

5/5(49 reviews)

Soak up the atmosphere as you stroll along this oceanfront strip, the heart of Virginia Beach’s dining and entertainment scene.

Virginia Beach Boardwalk
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.