Chesapeake Beach Vacation Packages

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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!

Top Chesapeake Beach Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
8/10 Very Good! (848 reviews)
Odd people roaming around

Reviewed on Jul. 14, 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,000 reviews)
This was a beautiful hotel. Very accommodating, complimentary early check in and late check out. Very clean, beautiful rooms, huge bathroom/shower. So location convenient. Close to Starbucks, restaurants and 2 minute walk to the event I went to, at the pier. Can’t say enough good things about this place.

Reviewed on Jul. 12, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Save 100% on your flight
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (1,001 reviews)
The staff was very nice and attentive to issues, but overall the property was a bit run down, smaller for what you pay for, dog barking constantly next door, TV didn't work, and Rollaway wasn't in room as requested. The price is truly for location and history, but truly don't think worth the price when extras that would normally be included in the price of the hotel, you had to pay extra.

Reviewed on Jul. 13, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
10/10 Exceptional! (12 reviews)
It’s a nice facility. The room was clean and spacious. Bathroom was well appointed. They have a nice cocktail bar and a restaurant. I did not have dinner there, I did have a couple of cocktails and some apps in the cocktail bar. Definitely recommend making time to stop there.

Reviewed on Jul. 13, 2025

The Melrose Georgetown Hotel

The Melrose Georgetown Hotel

4 out of 5
Northwest
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (2,303 reviews)
Nice and centrally located

Reviewed on Jul. 7, 2025

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 8 kilometres from the town centre, Breezy Point Beach is the place to be for many sun-seeking travellers. Have a look through our Chesapeake Beach vacation deals and watch your travel budget stretch further!

Ready to book your vacation to Chesapeake Beach?

 

Choose your dates

Chesapeake Beach Hotel Deals

Rod 'N' Reel Resort
Rod 'N' Reel Resort
4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
The price is CA $208 per night from Jul 15 to Jul 16
CA $208
CA $259 total
Jul 15 - Jul 16
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Lovely place"

Reviewed on Jul. 10, 2025

Rod 'N' Reel Resort
La Quinta Inn by Wyndham Waldorf
La Quinta Inn by Wyndham Waldorf
3 out of 5
11770 Business Park Dr, Waldorf, MD
The price is CA $133 per night from Jul 17 to Jul 18
CA $133
CA $147 total
Jul 17 - Jul 18
includes taxes & fees
7.4/10 Good! (999 reviews)
"NA"

Reviewed on Jul. 8, 2025

La Quinta Inn by Wyndham Waldorf
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 CA $134 per night from Jul 27 to Jul 28
CA $134
CA $152 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Rooms were clean and modern as was the TV. I was disappointed that this hotel has decided to charge for parking nightly via an app. Free parking at this level of hotel is a given normally, this is not a hotel in NYC, LA etc."

Reviewed on Jul. 11, 2025

SpringHill Suites by Marriott Annapolis
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Chesapeake Beach

Chesapeake Beach Water Park

Chesapeake Beach Water Park

3.5/5(2 reviews)

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

What to do in Chesapeake Beach

Sunset Cruise - On the Chesapeake Bay

Sunset Cruise on the Scenic & Calming Chesapeake Bay

CA $168
per adult
Sunset Cruise on the Scenic & Calming Chesapeake Bay
Enjoy A Beautiful Day With Mother Nature Cruises

Enjoying A Beautiful Day With Mother Nature Cruises

CA $139
per adult
Enjoying A Beautiful Day With Mother Nature Cruises
Chesapeake Beach: Guided Walking Tour of the Railway Trail

Chesapeake Beach: Guided Walking Tour of the Railway Trail

CA $56
per adult
Chesapeake Beach: Guided Walking Tour of the Railway Trail
See all activities in Chesapeake Beach

Frequently asked questions

How much does a Chesapeake Beach vacation package cost?
Offering great value package deals from CA $497 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. Travelling in quieter periods means you can usually find lower prices on accommodations and flights.
How many days is enough for Chesapeake Beach?
Generally, a handful of days is enough for a Chesapeake Beach vacation. With a well-organized schedule, you can see all the popular sights including Chesapeake Beach Railway Museum, as well as explore some hidden treasures along the way.
Is it worth booking a vacation package to Chesapeake Beach?
Whether you want to explore key attractions like Chesapeake Beach Water Park and Chesapeake Beach Railway Museum on your Chesapeake Beach vacation, or coming for its great family-friendly attractions, history and watersports, there's something for everyone here. With so much to do, you'll soon find out why so many travellers think Chesapeake Beach is a good vacation destination.
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 travellers 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.

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