We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chesapeake Vacation Packages

Chesapeake Arboretum
World Class Fishing
Carafe Wine Makers - Make Your Own Private Label Wine
Chesapeake Vacation Packages
Want to book a vacation to Chesapeake? Whether you're off for a romantic vacation, family trip, or an all-inclusive holiday, Chesapeake vacation packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect vacation package for Chesapeake on TripAdvisor by comparing Chesapeake hotel and flight prices. Travelers like you have written 3,845 reviews and posted 1,701 candid photos for Chesapeake hotels. Book your Chesapeake vacation today!
Or build your own Chesapeake vacation package
Comfort Suites
#1 Hotel in Chesapeake
Comfort Suites
Hotel is centrally located near a lot of businesses, restaurants, etc. and makes it easy to get around. Our King room was on the 3rd floor and very quiet. The bed was...
1. Find your perfect hotel
2. Find the right flight
FairField Inn & Suites by Marriott Chesapeake
#2 Hotel in Chesapeake
FairField Inn & Suites by Marriott Chesapeake
Since I had not stayed at the Fairfield Inn previously, I was a little reluctant however, it turned out to be a great choice. The property is well kept, the staff is very...
1. Find your perfect hotel
2. Find the right flight
Hampton Inn & Suites Chesapeake-Battlefield Blvd.
#3 Hotel in Chesapeake
Hampton Inn & Suites Chesapeake-Battlefield Blvd.
We stayed in a King suite. It was roomy and quite nice. The room was quiet. The bed comfortable and the other amenities were excellent. This hotel is pet-friendly. Our small dog...
1. Find your perfect hotel
2. Find the right flight
Cheap Flights to Chesapeake
May
find price round trip
Jun
find price round trip
Jul
find price round trip
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.