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 371
AED 534 total
3 Sep - 4 Sep
includes taxes & fees
8.6/10 Excellent! (1,016 reviews)
"If you are looking for a calm get away with everything you need minutes away I would recommend staying at the resort. There is so much to do at the resort to keep you busy! If you are lucky as I was there was a concert one of the nights of my stay. The cafe was amazing! The food was fresh and my ..."

Reviewed on 23 August 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 304
AED 335 total
31 Aug - 1 Sep
includes taxes & fees
8/10 Very Good! (1,018 reviews)
"It seems the hotel is under going renovation. Parts of it were nice and updated, others were very rundown looking. The staff were all very friendly and helpful. Our room was fine, bed was comfortable, it looked newly updated which was nice. The breakfast was typical hotel continental. It's a good ..."

Reviewed on 24 August 2026

St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
AED 1,563
AED 1,719 total
7 Sep - 8 Sep
includes taxes & fees
9.6/10 Exceptional! (397 reviews)
"Amazing experience highly recommend"

Reviewed on 16 August 2026

Inn at Perry Cabin
See all 781 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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Rod n Reel Charter Fishing

7.6/10 (31 reviews)
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.
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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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