Chesapeake Beach Holidays

Photo by Ronanne Vinson
    deals illustration

    Better together

    Save up to S$134 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

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

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!

Top hotels in Chesapeake Beach

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 S$242 per night from 9 Jul to 10 Jul
S$242
9 Jul - 10 Jul
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"We had the pleasure of staying here for 3 nights July 4th weekend. There was an issue with the kitchen at The Dock and we did not get our food because of a hour and a half back up . Mary overheard me talking to the front desk about it and was able to get us some food . She was so pleasant and kind ..."

Reviewed on 6 Jul, 2025

Rod 'N' Reel Resort
La Quinta Inn by Wyndham Waldorf
La Quinta Inn by Wyndham Waldorf
3 out of 5
11770 Business Park Dr, Waldorf, MD
Fully refundableReserve now, pay when you stay
The price is S$119 per night from 13 Jul to 14 Jul
S$119
13 Jul - 14 Jul
includes taxes & fees
7.4/10 Good! (1,000 reviews)
"Very friendly and a helpful when needed"

Reviewed on 29 Jun, 2025

La Quinta Inn by Wyndham Waldorf
SpringHill Suites by Marriott Annapolis
SpringHill Suites by Marriott Annapolis
3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
The price is S$148 per night from 13 Jul to 14 Jul
S$148
13 Jul - 14 Jul
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Great experience."

Reviewed on 4 Jul, 2025

SpringHill Suites by Marriott Annapolis
See all 737 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.

Popular places to visit

Rod n Reel Charter Fishing

Explore the waterfront in Chesapeake Beach with a trip to Rod n Reel Charter Fishing. Visit the spas in this relaxing area or simply enjoy its restaurants.

Rod n Reel Charter Fishing

What to do in Chesapeake Beach

Sunset Cruise - On the Chesapeake Bay

Sunset Cruise on the Scenic & Calming Chesapeake Bay

S$157
per adult
Sunset Cruise on the Scenic & Calming Chesapeake Bay
Enjoy A Beautiful Day With Mother Nature Cruises

Enjoying A Beautiful Day With Mother Nature Cruises

S$130
per adult
Enjoying A Beautiful Day With Mother Nature Cruises
Chesapeake Beach: Guided Walking Tour of the Railway Trail

Chesapeake Beach: Guided Walking Tour of the Railway Trail

S$53
per adult
Chesapeake Beach: Guided Walking Tour of the Railway Trail
See all activities in Chesapeake Beach

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.