Chesapeake Bay Vacations from $265

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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 favorite. 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.

The Latest Chesapeake Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
Club Wyndham Kingsgate
Linden Row Inn
Griffin Hotel, an official Colonial Williamsburg Hotel
The Colonies at Williamsburg
Wedmore Place
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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

Discover the most popular places to visit in Chesapeake Bay

What to do in Chesapeake Bay

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
$99 nightly
The price is $115 total per night from Aug 27 to Aug 28
$115 total
Aug 27 - Aug 28
Total with taxes and fees
8.6/10 Excellent! (4,576 reviews)
Great location
"Great location and good breakfast"

Reviewed on Aug 25, 2025

Washington Plaza 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
$131 nightly
The price is $147 total per night from Aug 31 to Sep 1
$147 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (2,664 reviews)
"The hotel was very beautiful, but we were a little disappointed that the front entrance was blocked off for construction. When we got into our room it wasn't exactly as described (which wasn't a big deal) and there was a hair clip on the floor, and the bathroom was very visibly not clean. We ended ..."

Reviewed on Aug 25, 2025

Hamilton Hotel Washington DC
The Henley Park Hotel

The Henley Park Hotel

4 out of 5
926 Massachusetts Ave NW, Washington, DC
$103 nightly
The price is $120 total per night from Aug 27 to Aug 28
$120 total
Aug 27 - Aug 28
Total with taxes and fees
9/10 Wonderful! (1,161 reviews)
"An amazing hotel, great ambience and in a very convenient location for the convention center. Highly recommended!"

Reviewed on Aug 25, 2025

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