Chesapeake Beach Vacations

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Stay near popular Chesapeake Beach attractions

A coastal residential area with houses along the beach and a lighthouse in the distance.

Breezy Point Beach

8.4/10 (61 reviews)
Stroll this half-mile Chesapeake Bay shoreline where gentle waves meet fossil-hunting adventures. Relax in shaded picnic areas after swimming in the netted area or trying your luck at the 200-foot fishing pier.
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A water park with a large pool, a yellow slide, and a lookout tower.
Photo by Ronanne Vinson

Chesapeake Beach Water Park

8.2/10 (88 reviews)
This family-friendly water park offers water slides, a lazy river, and pools for all ages. Currently closed for renovations until 2027, it will reopen with modernized facilities and new attractions.
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Chesapeake Beach Railway Museum

8.0/10 (34 reviews)
Housed in the original 1898 railway station, this museum chronicles Chesapeake Beach Resort's golden era. View authentic artifacts and a restored vintage railway car while exploring early 20th century coastal tourism.
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Bruce Gabrielson's Surf Art Gallery and Museum

7.8/10 (19 reviews)
Maryland's only surfing museum showcases Bruce Gabrielson's 50-year collection of historic boards and rare artifacts. Visitors can arrange private tours to see Duke Kahanamoku exhibits and Dale Velzy's shaping equipment.
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Brownies Beach

Why not spend a lazy afternoon at Brownies Beach during your trip to Chesapeake Beach? Stroll along this relaxing area's beaches, or simply enjoy its restaurants.
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What to do in Chesapeake Beach

Chesapeake Beach: Sunset Sailing Cruise with Snacks

Chesapeake Beach: Sunset Sailing Cruise with Snacks

$114
per adult
Chesapeake Beach: Sunset Sailing Cruise with Snacks
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Chesapeake Beach Hotel Deals

Rod 'N' Reel Resort

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
$162 nightly
$180 total
Oct 8 - Oct 9
Total with taxes and fees
Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
$99 nightly
$109 total
Oct 4 - Oct 5
Total with taxes and fees
St Michaels Inn
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

170 Admiral Cochrane Dr Edgewater MD
Fully refundableReserve now, pay when you stay
$97 nightly
$110 total
Sep 27 - Sep 28
Total with taxes and fees
Sonesta ES Suites Annapolis
See all 784 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.

Find the Best Chesapeake Beach Vacation Packages

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Frequently asked questions

How much does a Chesapeake Beach vacation package cost?
You can grab a vacation package to this destination on Expedia. But how much your vacation 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?
July, September and December are the best times to search for cheap Chesapeake Beach vacation packages. Opting to travel in quieter periods means you can typically find lower prices on accommodations and flights.
How many days is enough for Chesapeake Beach?
You can easily explore all the leading sights in Chesapeake Beach within a few days, including the must-see Bruce Gabrielson's Surf Art Gallery and Museum. If you're looking for an extended Chesapeake Beach vacation, look at what sort of activities and day trips are available nearby.
Is it worth booking a vacation package to Chesapeake Beach?
Chesapeake Beach has everything you need for the perfect break — history, watersports and culture are just the start. Whether you want to visit sights such as Chesapeake Beach Water Park and Chesapeake Beach Railway Museum, or take the road less traveled, you'll have plenty to see and do on your Chesapeake Beach vacation.
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 vacation package as soon as possible.
Is it cheaper to book a Chesapeake Beach vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and accommodations separately. Better still, you can personalize 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 vacation 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 the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Chesapeake Beach.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to airfares and activities. Your hotel will likely be the largest expense during your trip to Chesapeake Beach.
  3. Organize your Chesapeake Beach escape with our trip planning tool: Search for and book stays and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Chesapeake Beach together.
  4. Determine how many days away: Start by listing all the sights and activities you want to experience in Chesapeake Beach. Then, estimate how long you'll need for each, along with any travel time.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Chesapeake Beach vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Have a look at our travel guide to find some incredible things to do in Chesapeake Beach in Chesapeake Beach. Book tickets or make reservations in advance to save time and avoid the stress of searching for activities once you arrive.
Does Expedia offer Book Now, Pay Later Chesapeake Beach vacation packages?
If you're like us, you love going away but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Chesapeake Beach trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

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