Chesapeake Beach Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Ronanne Vinson

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
8.2/10 Very Good! (1,001 reviews)
"Huge resort in a small, well kept town! Our room was right on the bay and was clean and nice. The beds and pillows were super comfortable. There is not a place for breakfast but if you go a little further south on the main road, there is a shopping center with a McDonalds (and a CVS and some other ..."

Reviewed on 16 Jun 2025

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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 2.645.781 ₫ per night from 9 Jul to 10 Jul
2.645.781 ₫
3.016.191 ₫ total
9 Jul - 10 Jul
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Arrival went well; however, the property assessed an unannounced self-parking fee of $9.50 per night. Spent only two nights but got no towel or trash service. Would have been nice to know so we could rinse wash clothes. Luckily we read the eco signs in the room asking us to hang up towels to dry ..."

Reviewed on 21 Jun 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 2.957.049 ₫ per night from 9 Jul to 10 Jul
2.957.049 ₫
3.371.036 ₫ total
9 Jul - 10 Jul
includes taxes & fees
8.8/10 Excellent! (825 reviews)
"Room was large & bed very comfortable. Very pleasant stay"

Reviewed on 22 Jun 2025

Sonesta ES Suites Annapolis
See all 733 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.

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.

Popular places to visit

Breezy Point Beach

Why not spend a care-free afternoon at Breezy Point Beach during your travels in Chesapeake Beach? Visit the spas in this relaxing area or simply enjoy its restaurants.

Breezy Point Beach

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