Chesapeake Beach Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Ronanne Vinson

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Chesapeake Beach Holiday

The family-friendly attractions and laid-back lifestyle are just the beginning of the things Chesapeake Beach has going for it. Enjoy the best of this interesting city the way you want with a tailor-made Chesapeake Beach holiday package. Make your trip to Chesapeake Beach even more fulfilling by including some sightseeing. Breezy Point Beach, Chesapeake Beach Water Park and Bayside History Museum are some of the big attractions worth exploring. Expedia can help you escape the everyday. Tailor your holiday to Chesapeake Beach to suit your style of travel, whatever that may be.

Chesapeake Beach Holiday

Chesapeake Beach Beach Holiday

Live out those beachy daydreams on your Chesapeake Beach holiday. Enjoy a relaxing stroll, marvel at the beautiful coastal vistas and collect pretty seashells during your trip to Chesapeake Beach. Just 8 kilometres from the town centre, Breezy Point Beach is the place to be for many sun-seeking travellers. Have a look through our Chesapeake Beach holiday deals and watch your travel budget stretch further!

Chesapeake Beach Essential Information

Language
English
Currency
U.S dollars
Population
5,900
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
Breezy Point Beach, Chesapeake Beach Water Park and Bayside History Museum

Our pick of the best Chesapeake Beach Hotel Deals

Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is AU$288 per night from 27 July to 28 July
AU$288
27 July - 28 July
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
"No where to walk."

Reviewed on 22 Jul. 2025

Rod 'N' Reel Resort
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 3 Aug to 4 Aug
AU$168
3 Aug - 4 Aug
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"There was nothing wrong with the place or room. Just a little surprised to have to pay an extra $10 a night for parking."

Reviewed on 22 Jul. 2025

SpringHill Suites by Marriott Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
Fully refundableReserve now, pay when you stay
The price is AU$170 per night from 27 July to 28 July
AU$170
27 July - 28 July
includes taxes & fees
8.8/10 Excellent! (841 reviews)
"Great room for a great price... Very friendly staff, too."

Reviewed on 17 Jul. 2025

Sonesta ES Suites Annapolis
See all 734 properties in Chesapeake Beach
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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Chesapeake Beach holiday package cost?
You can grab a holiday package to this destination on Expedia. But how much your holiday to Chesapeake Beach costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Chesapeake Beach?
If you'd like to score a cheap Chesapeake Beach holiday package, consider travelling in January, February and April. You're likely to find better prices on hotels and flights during these months — ideal for a budget-friendly getaway.
How many days is enough for Chesapeake Beach?
You can easily visit all the top attractions in Chesapeake Beach within a few days, including the must-see Bruce Gabrielson's Surf Art Gallery and Museum. If you're after a longer Chesapeake Beach holiday, look at which kind of excursions and activities are available in the area.
Is it worth booking a holiday package to Chesapeake Beach?
Chesapeake Beach has all the ingredients you need for an awesome break — family-friendly attractions, history and watersports are just the start. Whether you'd like to visit sights like Chesapeake Beach Water Park and Chesapeake Beach Railway Museum, or take the road less traveled, you'll find plenty to see and do on your Chesapeake Beach holiday.
How to find the best Chesapeake Beach package deals?
Use Expedia's filter tool to help you find some tempting Chesapeake Beach package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Chesapeake Beach package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Chesapeake Beach holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and accommodation separately. Better still, you can personalise your Chesapeake Beach escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Chesapeake Beach?
Secure fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chesapeake Beach trip.
How to plan a trip to Chesapeake Beach?

  1. Choose when to get away: Check your diary and get packing. Your preferred time of year and the type of activities on offer will also help you decide when to holiday in Chesapeake Beach.
  2. Budget wisely: As well as the price of your stay, you should factor in other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Chesapeake Beach.
  3. Decide how long to go for: Now that you're up to speed on Chesapeake Beach, you can work out the ideal length of your holiday. Put together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick a Chesapeake Beach holiday package that brings all your bookings together.

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