Chesapeake Beach Vacations

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Photo by Ronanne Vinson

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Find the Best Chesapeake Beach Vacation Packages

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 AED 348 per night from Feb 16 to Feb 17
AED 348
AED 459 total
16 Feb - 17 Feb
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Nice staff

Reviewed on 7 February 2026

Rod 'N' Reel Resort
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Chesapeake Beach MD
10/10 Exceptional! (85 reviews)
What a fantastic spot! The views are amazing. The kitchen was the best-appointed we’ve ever experienced. The heated floors for winter were wonderful.

Reviewed on 1 December 2025

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Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
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 AED 334 per night from Mar 1 to Mar 2
AED 334
AED 381 total
1 Mar - 2 Mar
includes taxes & fees
8.8/10 Excellent! (985 reviews)
We were happy to stay at this place. Very beautiful, warm, comfortable ❤️❤️❤️

Reviewed on 3 February 2026

Sonesta ES Suites Annapolis
See all 738 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.

Discover the most popular places to visit in Chesapeake Beach

Family fun at Chesapeake Beach Water Park in Calvert County, Maryland.

Chesapeake Beach Water Park

4.5/5(22 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

Bruce Gabrielson's Surf Art Gallery and Museum

You can spend an afternoon studying the exhibits at Bruce Gabrielson's Surf Art Gallery and Museum during your trip to Chesapeake Beach. Stroll along this relaxing area's beaches, or simply enjoy its restaurants.

Bruce Gabrielson's Surf Art Gallery and Museum

Frequently asked questions

How do I find cheap flights to Chesapeake Beach that have flexible change policies?
At Expedia, we've been channeling our inner yogi to give you the most flexible fares in town. Simply check the "No change fee" box directly below the filter heading "Flexible change policies" to find the best flights to Chesapeake Beach.
Which airlines fly to Chesapeake Beach?
Take your pick of a selection of airlines that operate flights into or near Chesapeake Beach. Here are a few of the best:

  • American Airlines - 7,098 flights to or near Chesapeake Beach each month, including 6,885 flights to Ronald Reagan Washington National Airport (DCA) and 212 to Washington Dulles Intl. Airport (IAD) per month.
  • United Airlines - 6,077 flights to or near Chesapeake Beach each month, including 5,270 flights to Washington Dulles Intl. Airport (IAD) and 806 to Ronald Reagan Washington National Airport (DCA) per month.
  • Delta Air Lines - 1,659 flights to or near Chesapeake Beach each month, including 1,304 flights to Ronald Reagan Washington National Airport (DCA) and 355 to Washington Dulles Intl. Airport (IAD) per month.

How can I find cheap tickets to Chesapeake Beach?
In the last seven days, was the best price for a flight to Chesapeake Beach. If you're eager to save even more, book ahead of time and be flexible with your dates. Search for your journey to Chesapeake Beach, then see prices for similar time frames by clicking on the "flexible dates" link above.
How much is a flight to Chesapeake Beach?
There were a lot of bargain fares up for grabs in the last seven days, with the cost of a round-trip flight to Chesapeake Beach varying between and . Many lucky travelers nabbed one-way flights from () for as low as .
What are the most popular airports to fly into in Chesapeake Beach?
When you've planned where you're going in Chesapeake Beach, choose from these well-known airports:

  • Ronald Reagan Washington National Airport (DCA) - 11,147 flights per month.
  • Washington Dulles Intl. Airport (IAD) - 6,388 flights per month.

When is the cheapest time to fly to Chesapeake Beach?
If you'd prefer to spend your vacation savings on having fun in Chesapeake Beach rather than on getting there, depart earlier in the week. The cheapest day to fly is normally Tuesday, with Monday a close second. With many people keeping their travel to weekends, Saturday typically has the most expensive fares.
How much is a plane ticket to Chesapeake Beach?
Airfares ranged from just to over the last seven days. When you're ready to book, we'll help you land an awesome deal to Chesapeake Beach.
What months are the cheapest to book a flight to Chesapeake Beach?
February is the most affordable month to lock in a seat for your Chesapeake Beach escape. Airfares are at their most expensive during the busy month of December, so avoid this time if you can.
How long is a flight to Chesapeake Beach?
Whether or not you'll have time to binge-watch your favorite series depends on where you're taking off from. To give you a rough estimate, here are the average flight times for some well-known domestic routes to Chesapeake Beach:

  • Boston, MA (BOS-Logan Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 44 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 46 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 51 minutes