
Chesapeake Bay Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Chesapeake Bay vacation package deals
Price found within the past 48 hours. Click for updated prices.

3.0-star property
Vacation Village At Williamsburg
8.8/10 Excellent! (1,732 reviews)
Oct 26 - Oct 31
5 night stay
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
United • Coach
Richmond (RIC) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Price was $507, price is now $391 per person
$391
per person
found 1 day ago
Great location and friendly staff!
Reviewed on Sep 18, 2025

3.0-star property
Griffin Hotel, an official Colonial Williamsburg Hotel
Colonial Williamsburg
8.8/10 Excellent! (744 reviews)
Oct 26 - Oct 31
5 night stay
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
United • Coach
Richmond (RIC) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Price was $745, price is now $545 per person
$545
per person
found 1 day ago
Confusing check-in with the related griffin hotel
Reviewed on Jun 26, 2023

3.0-star property
The Colonies at Williamsburg
9/10 Wonderful! (1,022 reviews)
Oct 26 - Oct 31
5 night stay
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
United • Coach
Richmond (RIC) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Price was $752, price is now $575 per person
$575
per person
found 1 day ago
Need hand rails in shower
Reviewed on Aug 27, 2024

3.0-star property
Club Wyndham Kingsgate
8.8/10 Excellent! (1,002 reviews)
Oct 26 - Oct 31
5 night stay
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
United • Coach
Richmond (RIC) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Price was $614, price is now $471 per person
$471
per person
found 1 day ago
Lots of fun things for kids to do and everyone was friendly loved that add one we’re all included so kids could enjoy it all
Reviewed on Nov 4, 2024

3.0-star property
Club Wyndham Governor’s Green
9.2/10 Wonderful! (222 reviews)
Oct 26 - Oct 31
5 night stay
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
United • Coach
Richmond (RIC) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Price was $699, price is now $545 per person
$545
per person
found 1 day ago
The check in process was easy and efficient. The grounds themselves are well maintained. The room was spacious and clean! Overall, we would recommend this resort to anyone.
Reviewed on Nov 5, 2021
Top rated hotels for your Chesapeake Bay vacation package

Washington Plaza Hotel
10 Thomas Circle NW, Washington, DC
Free Cancellation
Reserve now, pay when you stay
108 mi from city center
$109 nightly
The price is $126 total per night
$126 total
Sep 21 - Sep 22
Total with taxes and fees
Guests of Washington Plaza Hotel have access to an outdoor pool, a 24-hour gym, and free WiFi in public areas. Self parking is offered for USD 43 per night. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, tours or tickets, and dry cleaning/laundry. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pool
Free WiFi

Hamilton Hotel Washington DC
1001 14th St NW, Washington, DC
Free Cancellation
Reserve now, pay when you stay
107.83 mi from city center
$200 nightly
The price is $227 total per night
$227 total
Sep 21 - Sep 22
Total with taxes and fees
Hamilton Hotel Washington DC features a gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 69 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include a microwave in a common area, a terrace, and a ballroom.
Free WiFi
Restaurant

Hyatt Regency Baltimore Inner Harbor
300 Light Street, Baltimore, MD
Free Cancellation
Reserve now, pay when you stay
124.87 mi from city center
$169 nightly
The price is $199 total per night
$199 total
Oct 3 - Oct 4
Total with taxes and fees
Guests staying at Hyatt Regency Baltimore Inner Harbor enjoy a 24-hour gym, a rooftop terrace, and free WiFi in public areas. Valet parking is available for USD 48 per day. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls and an off-leash area. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Pet friendly
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.
More trip options
- Nearby Destinations
- Destinations similar to Chesapeake Bay
- Best neighborhoods in Chesapeake Bay
- More to explore for Chesapeake Bay
- Top trending
- Book on Expedia
Top trending
Hotels
- Pocono Mountains All Inclusive Resorts & Hotels
- Pocono Mountains Romantic Getaways & Hotels
- Pocono Mountains Hotels with Hot Tubs
- Florida Keys Hotel Deals
- Gulf Coast Kid Friendly Hotels
- Gulf Coast Waterpark Hotels & Resorts
- Pocono Mountains Spa Resorts & Hotels
- Southern California Hotels with a Lazy River
- Northern California Casino Resorts & Hotels
- Southeastern United States All Inclusive Resorts & Hotels
- Western United States All Inclusive Resorts & Hotels
- Southern California Hotels with Waterslides
- Florida Keys Beach Resorts & Hotels
- Southern California Spa Resorts & Hotels
- Northern California Kid Friendly Hotels
- Pocono Mountains Hotel Deals
- Pocono Mountains Waterpark Hotels & Resorts
- Florida Keys Hotels with Waterslides
- Northern California All Inclusive Resorts & Hotels
- Northern California Beach Resorts & Hotels
- Southern California Hotels with Hot Tubs
- Gulf Coast Beach Resorts & Hotels
- Northern California Spa Resorts & Hotels
- Southern California Hotels with an Indoor Pool
- Florida Keys Cheap Hotels
- Pocono Mountains Hotels with an Indoor Pool
- Florida Keys All Inclusive Resorts & Hotels
- Quad Cities Hotels with Hot Tubs
Flights
Packages