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 27 - Oct 30
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8/10 Very Good! (968 reviews)
Acceptable for my one night stay

Reviewed on Aug. 8, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
per person
Oct 27 - Oct 30
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.6/10 Excellent! (1,005 reviews)
Very well located. Felt safe to walk all times of day and night. Great food spots located all around. Subway not too far from it as well, only like .04 miles from it. Great staff. Will definitely stay there next time I return to D.C

Reviewed on Aug. 8, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
per person
Sep 19 - Sep 22
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.8/10 Exceptional! (28 reviews)
Absolutely incredible hotel that we happened upon on a whim. Brand new, absolutely stunning and Johnny the concierge made our night and had us feeling right at home despite the grandeur of the establishment. Can’t recommend this place enough and shout out to Johnny ❤️

Reviewed on Aug. 3, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
per person
Sep 19 - Sep 22
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (1,004 reviews)
Amenities in the room were very nice quality, slippers, loofah, and toiletries. I was overcharged for car parking on check out when they asked if I had any extras. Hotel refunded it right away but my overseas bank took an extra procedure fee as a result of this misunderstanding. Room was a suite but the hallway between had no light. View was excellent.

Reviewed on Aug. 7, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
per person
Sep 19 - Sep 22
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.4/10 Exceptional! (1,002 reviews)
Great location, facility, amenities and friendly staff

Reviewed on Aug. 9, 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?

 

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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
The price is CA $185 per night from Aug 10 to Aug 11
CA $185
CA $232 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Great options"

Reviewed on Aug. 3, 2025

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
The price is CA $125 per night from Sep 2 to Sep 3
CA $125
CA $143 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (851 reviews)
"Great room for a great price... Very friendly staff, too."

Reviewed on Jul. 17, 2025

Sonesta ES Suites Annapolis
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 $145 per night from Aug 17 to Aug 18
CA $145
CA $165 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"It was very clean"

Reviewed on Aug. 8, 2025

SpringHill Suites by Marriott Annapolis
See all 739 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

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

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
North Beach: North Beach Historic Guided Walking Tour

North Beach: North Beach Historic Guided Walking Tour

CA $65
per adult
North Beach: North Beach Historic Guided Walking Tour
North Beach: North Beach Scenic Guided Walking Tour

North Beach: North Beach Scenic Guided Walking Tour

CA $56
per adult
North Beach: North Beach Scenic Guided Walking Tour
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 $463 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.