Chesapeake Beach Vacations

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Find the Best Chesapeake Beach Vacation Packages

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
AED 494
AED 548 total
20 Oct - 21 Oct
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Great local getaway on the water."

Reviewed on 7 October 2026

Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
AED 327
AED 360 total
19 Oct - 20 Oct
includes taxes & 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
AED 334
AED 381 total
27 Oct - 28 Oct
includes taxes & fees
Sonesta ES Suites Annapolis
See all 783 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.

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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Frequently asked questions

How much does a Chesapeake Beach vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Chesapeake Beach costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chesapeake Beach?
January, February and April are the best times to look for cheap Chesapeake Beach vacation packages. Traveling in quieter periods means you can usually find lower prices on accommodations and flights.
How to find the best Chesapeake Beach package deals?
Finding a cheap Chesapeake Beach package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Chesapeake Beach package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Chesapeake Beach vacation as a package?
You can enjoy significant savings on your next Chesapeake Beach break by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Chesapeake Beach?
If you're considering an impromptu Chesapeake Beach trip, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Chesapeake Beach?
  1. Choose your travel dates: What you'd like to do in Chesapeake Beach and your preferred season can help you decide when to go.
  2. Plan your budget wisely: On top of the cost of your stay, you'll need to factor in other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may come up during your trip to Chesapeake Beach.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to get to in Chesapeake Beach. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your accommodations and airfare: After you've settled on your travel dates and duration, book the perfect Chesapeake Beach vacation package for you.

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