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.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

2.5 out of 5
Short Pump
Price was CA $1,346, price is now CA $1,058 per person
CA $1,058
per person
Oct 8 - Oct 14
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.6/10 Excellent! (1,827 reviews)
Clean and comfortable, quiet. Breakfast was alright, coffee was good

Reviewed on Sep. 1, 2025

Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was CA $1,849, price is now CA $1,231 per person
CA $1,231
per person
Oct 8 - Oct 14
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.4/10 Very Good! (1,337 reviews)
Loved the attention to detail. Design is functional and entertaining at the same time Staff is amazing. Loved having a coffee bar on site. Valet parking was well structured but expensive.

Reviewed on Sep. 4, 2025

Warner Hall

Warner Hall

3 out of 5
Price was CA $1,832, price is now CA $1,444 per person
CA $1,444
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Richmond (RIC)
10/10 Exceptional! (13 reviews)
Great staff and attitude toward customers.

Reviewed on Aug. 3, 2025

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was CA $1,460, price is now CA $1,179 per person
CA $1,179
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (737 reviews)
The property is very large and offers many amenities, including spa and pools and golf. There are many restaurants in the different hotels that are part of the compound. The staff were very helpful and nice

Reviewed on Aug. 21, 2025

Westgate Williamsburg

Westgate Williamsburg

2.5 out of 5
Price was CA $2,441, price is now CA $2,005 per person
CA $2,005
per person
Oct 26 - Nov 2
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
4/10 (1 review)

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. featuring night scenes, street scenes and a city

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

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 $184 per night from Oct 2 to Oct 3
CA $184
CA $255 total
Oct 2 - Oct 3
includes taxes & fees
Hamilton Hotel Washington DC
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 $150 per night from Sep 7 to Sep 8
CA $150
CA $174 total
Sep 7 - Sep 8
includes taxes & fees
Washington Plaza Hotel
Hyatt Regency Baltimore Inner Harbor

Hyatt Regency Baltimore Inner Harbor

4 out of 5
300 Light Street, Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Sep 21 to Sep 22
CA $233
CA $274 total
Sep 21 - Sep 22
includes taxes & fees
Hyatt Regency Baltimore Inner Harbor
See all 15,078 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

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
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
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
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

CA $44
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

CA $41
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Chesapeake Bay

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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.