Chesapeake Beach Vacations from $424

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Your Chesapeake Beach Vacation

Lock in a Chesapeake Beach vacation package and prepare for an exciting getaway. Noted for its family-friendly attractions and laid-back lifestyle, there's lots to like about this lively city. You'll want to do some exploring during your trip to Chesapeake Beach. Drop by famous attractions like Breezy Point Beach, Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. Stop daydreaming and start traveling. Explore the multitude of options on Expedia today and put your Chesapeake Beach vacation plans into action!

The Latest Chesapeake Beach vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Arlington/Courthouse Plaza

Hyatt Place Arlington/Courthouse Plaza

3 out of 5
Court House
Save 100% on your flight
Price was $593, price is now $424 per person
$424
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.2/10 Wonderful! (1,075 reviews)
I don’t have any pets. Nice small kitchen with full size frig.

Reviewed on Mar 25, 2026

Placemakr Buzzard Point

Placemakr Buzzard Point

4 out of 5
Southwest
Save 100% on your flight
Price was $958, price is now $644 per person
$644
per person
Jun 4 - Jun 7
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.2/10 Wonderful! (157 reviews)
I loved my stay there. The staff was so nice and helpful. I would definitely stay again.

Reviewed on Mar 5, 2026

Kimpton Hotel Monaco Washington DC by IHG

Kimpton Hotel Monaco Washington DC by IHG

4.5 out of 5
Downtown Washington D.C.
Price was $922, price is now $656 per person
$656
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.4/10 Very Good! (1,002 reviews)
Very nice hotel. Rooms are on the smaller side. Very convenient location.

Reviewed on Mar 21, 2026

Homewood Suites by Hilton Washington DC Convention Center

Homewood Suites by Hilton Washington DC Convention Center

3.5 out of 5
Downtown Washington D.C.
Price was $793, price is now $566 per person
$566
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.4/10 Very Good! (1,248 reviews)
I can not say enough great thing about this hotel, staff and accommodations. The staff was beyond friendly, our room was serviced everyday, the breakfast was great. It was one of the best hotel experiences we’ve had, and we’ve had a lot. It is close (within a mile) to everything you want to see while in DC. A safe area - we are a family of five with a 5, 10 and 12 year old and never felt not safe. There is a grocery store right across the street which was super convent!! Also, several great, reasonably priced restaurants within several feet of the hotel!

Reviewed on Mar 26, 2026

The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,130, price is now $810 per person
$810
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.8/10 Exceptional! (1,000 reviews)
Very friendly and professional staff

Reviewed on Mar 18, 2026

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Discover the most popular places to visit in Chesapeake Beach

Breezy Point New York Aerial View beach and houses

Breezy Point Beach

Why not spend a carefree 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
Family fun at Chesapeake Beach Water Park in Calvert County, Maryland.

Chesapeake Beach Water Park

Enjoy the thrill rides with your kiddos at Chesapeake Beach Water Park during your trip to Chesapeake Beach. Visit the spas in this relaxing area, or simply enjoy its restaurants.

Chesapeake Beach Water Park

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

Chesapeake Beach: Sunset Sailing Cruise with Snacks

Chesapeake Beach: Sunset Sailing Cruise with Snacks

$114
per adult
Chesapeake Beach: Sunset Sailing Cruise with Snacks
See all activities in Chesapeake Beach

Chesapeake Beach Hotel Deals

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
$133 nightly
The price is $146 total per night from Mar 30 to Mar 31
$146 total
Mar 30 - Mar 31
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
We were very impressed! We can’t wait to come back during the warmer months!

Reviewed on Mar 24, 2026

Rod 'N' Reel Resort
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
$89 nightly
The price is $102 total per night from Mar 29 to Mar 30
$102 total
Mar 29 - Mar 30
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
The room was clean, bed comfortable.

Reviewed on Mar 25, 2026

Sonesta ES Suites Annapolis
Spark by Hilton Waldorf

Spark by Hilton Waldorf

3 out of 5
11770 Business Park Drive Waldorf MD
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $99 total per night from Apr 5 to Apr 6
$99 total
Apr 5 - Apr 6
Total with taxes and fees
8.2/10 Very Good! (101 reviews)
The property itself isn’t bad but the noise volume was unbelievable. The Breakfast is nothing at all besides Cold cereal, coffee, and Oatmeal packets. The room have been semi remodeled but aren’t anything to brag about.

Reviewed on Mar 15, 2026

Spark by Hilton Waldorf
See all 736 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

Chesapeake Beach Beach Vacation

Live out those beachy daydreams on your Chesapeake Beach vacation. Enjoy a relaxing stroll, marvel at the beautiful coastal vistas and collect pretty seashells during your trip to Chesapeake Beach. Just 5 miles from the town center, Breezy Point Beach is the place to be for many sun-seeking travelers. Have a look through our Chesapeake Beach vacation deals and watch your travel budget stretch further!

Chesapeake Beach Essential Information

Language
English
Currency
U.S dollars
Population
5,900
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
Chesapeake Beach Water Park, Breezy Point Beach and Bayside History Museum

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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 from $424 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.