Chesapeake Bay Vacations from $329

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The Latest Chesapeake Bay Vacation Packages

Prices and availability subject to change. Additional terms may apply.
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
per person
Jun 30 - Jul 2
Roundtrip non-stop flight included
Orlando (MCO) to Richmond (RIC)
8/10 Very Good! (1,003 reviews)
The location is excellent and the front desk is warm and professional. It appears that some employees live and work in the old Princess Anne Motor Court section, which seems like a nice arrangement. However, during my stay they were making noise late at night and I cigarette smoke smell wafted into my room. I won't stay in these rooms again.

Reviewed on Apr 21, 2024

Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
per person
Jun 30 - Jul 2
Roundtrip non-stop flight included
Orlando (MCO) to Richmond (RIC)
9.8/10 Exceptional! (170 reviews)
Everything was perfect, great service!

Reviewed on Apr 6, 2024

Williamsburg Sampler B & B

Williamsburg Sampler B & B

3 out of 5
per person
Jun 30 - Jul 2
Roundtrip non-stop flight included
Orlando (MCO) to Richmond (RIC)
9.6/10 Exceptional! (300 reviews)
We thoroughly enjoyed our stay at the Williamsburg Sampler B & B. The accommodations were lovely - cozy and inviting decor with several different seating areas for guests downstairs to relax outside of their rooms in addition to a open and large kitchen - dining area. The rooms themselves were comfortable and well appointed. The Breakfasts were suburb! Stephanie, the B & B hostess out-did herself with her hospitality. Pluses included that Colonial Williamsburg and a variety of restaurants were within walking distance. We plan to go back.

Reviewed on Feb 21, 2024

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
per person
Jun 30 - Jul 2
Roundtrip non-stop flight included
Orlando (MCO) to Richmond (RIC)
8.8/10 Excellent! (1,002 reviews)
This property is very close to all major attractions in the area; a quiet area away from the congestion of Richmond Road yet a short walk to the restored section of CW. Planning on returning to enjoy the golfing opportunities in the immediate region.

Reviewed on Apr 19, 2024

Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
per person
Jun 30 - Jul 2
Roundtrip non-stop flight included
Orlando (MCO) to Richmond (RIC)
8.6/10 Excellent! (1,001 reviews)
Nice facilities and reasonably close to many dinning options and local historic sites.

Reviewed on Apr 23, 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.

1 out of top 10 points of interest in this area
4.5/5(6,676 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 Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Ronald Reagan Washington National Airport (DCA)

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 $156 per night from May 23 to May 24
$156
$181 total
includes taxes & fees
May 23 - May 24
8.6/10 Excellent! (3,148 reviews)
A remarkable stay
"It was an amazing stay and I enjoyed myself at your beautiful hotel."

Reviewed on Apr 22, 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 $195 per night from May 23 to May 24
$195
$226 total
includes taxes & fees
May 23 - May 24
8.4/10 Very Good! (1,258 reviews)
"Was convenient to the location of our event. Located in seemingly safe residential area. Staff very friendly and very helpful!"

Reviewed on Apr 25, 2024

Omni Shoreham Hotel
Hotel Pentagon
Hotel Pentagon
3 out of 5
2480 S Glebe Rd, Arlington, VA
Fully refundableReserve now, pay when you stay
The price is $118 per night from May 24 to May 25
$118
$135 total
includes taxes & fees
May 24 - May 25
6.4/10 (1,070 reviews)
"No frills but perfectly adequate - price is right, and very convenient for traveling professionals not spending a ton of time on property."

Reviewed on Apr 23, 2024

Hotel Pentagon
See all 14,188 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Chesapeake Bay vacation package cost?
Tailor make your Chesapeake Bay package from an affordable $329. 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

4.5/5(1,024 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(5,961 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 Virginia Beach Boardwalk

Virginia Beach Boardwalk

4.5/5(3,185 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

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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.