
Chesapeake Bay Vacation Packages
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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! (1,601 reviews)
Nov 9 - Nov 14
5 night stay
Jacksonville (JAX) to Richmond (RIC)
Delta • Non-stop • Coach
Richmond (RIC) to Jacksonville (JAX)
Breeze Airways • Non-stop • Coach
Price was $490, price is now $351 per person
$351
per person
found 21 hours ago
There was a lot of space for our family and 2 bathrooms was very convenient.
Reviewed on Aug 8, 2025

3.0-star property
Club Wyndham Kingsgate
8.8/10 Excellent! (1,004 reviews)
Nov 9 - Nov 14
5 night stay
Jacksonville (JAX) to Richmond (RIC)
Delta • Non-stop • Coach
Richmond (RIC) to Jacksonville (JAX)
Breeze Airways • Non-stop • Coach
Save 100% on your flight
Price was $624, price is now $414 per person
$414
per person
found 21 hours 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
Griffin Hotel, an official Colonial Williamsburg Hotel
Colonial Williamsburg
8.8/10 Excellent! (731 reviews)
Nov 9 - Nov 14
5 night stay
Jacksonville (JAX) to Richmond (RIC)
Delta • Non-stop • Coach
Richmond (RIC) to Jacksonville (JAX)
Breeze Airways • Non-stop • Coach
Save 100% on your flight
Price was $681, price is now $455 per person
$455
per person
found 21 hours 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! (1,012 reviews)
Nov 9 - Nov 14
5 night stay
Jacksonville (JAX) to Richmond (RIC)
Delta • Non-stop • Coach
Richmond (RIC) to Jacksonville (JAX)
Breeze Airways • Non-stop • Coach
Save 100% on your flight
Price was $746, price is now $506 per person
$506
per person
found 21 hours ago
Need hand rails in shower
Reviewed on Aug 27, 2024

2.5-star property
Westgate Williamsburg
No reviews
Nov 9 - Nov 14
5 night stay
Jacksonville (JAX) to Richmond (RIC)
Delta • Non-stop • Coach
Richmond (RIC) to Jacksonville (JAX)
Breeze Airways • Non-stop • Coach
Save 100% on your flight
Price was $1,193, price is now $844 per person
$844
per person
found 21 hours ago
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
$99 nightly
The price is $115 total per night
$115 total
Aug 22 - Aug 23
Total includes 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 luggage storage, dry cleaning/laundry, and concierge services. 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
$131 nightly
The price is $147 total per night
$147 total
Aug 31 - Sep 1
Total includes 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 luggage storage, dry cleaning/laundry, and securing valuables. Additional amenities include a microwave in a common area, a terrace, and a banquet hall.
Free WiFi
Restaurant

The Henley Park Hotel
926 Massachusetts Ave NW, Washington, DC
Free Cancellation
Reserve now, pay when you stay
107.69 mi from city center
$98 nightly
The price is $114 total per night
$114 total
Aug 28 - Aug 29
Total includes taxes and fees
At The Henley Park Hotel, guests have access to a gym, free WiFi in public areas, and a business center. Valet parking is offered for USD 56.64 per night. The 24-hour front desk has staff standing by to help with tours or tickets, securing valuables, and luggage storage. Other amenities at this luxury hotel include express check-out, a banquet hall, and a fireplace in the lobby.
Free WiFi
Restaurant
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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