Chesapeake Beach Vacations 2025 from CA $748

Chesapeake Beach flight + hotel packages

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

Hotel Nell - Union Market

Northeast

Save 100% on your flight

per person

May 15 - May 19

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to Washington (DCA)

Stay at this 3-star hotel in Washington. Enjoy 2 restaurants, 2 bars/lounges, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Union Station Shopping Center and Capital One Arena are located nearby.

Global Luxury Suites at Capitol Hill

Northeast

Save 100% on your flight

per person

Jun. 20 - Jun. 26

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Washington (DCA)

Stay at this 4-star aparthotel in Washington. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the clean rooms in our reviews. Popular attractions Union Station Shopping Center and Capital One Arena are located nearby.

Washington Hilton

Northwest

Save 100% on your flight

per person

Jun. 20 - Jun. 26

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Washington (DCA)

Book a stay at this business-friendly hotel in Washington. Enjoy an outdoor pool, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions White House and Capital One Arena are located nearby.

The Royal Sonesta Washington DC Dupont Circle

Northwest

Save 100% on your flight

per person

Jun. 20 - Jun. 26

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Washington (DCA)

Stay at this 4.5-star luxury hotel in Washington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.

The Normandy Hotel

Northwest

Save 100% on your flight

per person

Jun. 20 - Jun. 26

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Washington (DCA)

Stay at this 3-star business-friendly hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.

Top Chesapeake Beach hotels deals

Rod 'N' Reel Resort

4165 Mears Ave, Chesapeake Beach, MD

Free cancellation

Reserve now, pay when you stay

CA $166

CA $213 total

includes taxes & fees

13 Apr - 14 Apr

Stay at this 4-star business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chesapeake Beach Railway Museum and Rod n Reel Charter Fishing are located nearby.

Pool

Spa

Family Beach House: Spacious Deck, Grill & Views

CA $323

CA $715 total

includes taxes & fees

30 Apr - 1 May

Book a stay at this beach vacation home in Chesapeake Beach. Enjoy a beach locale, a garden, and patios. Popular attractions Breezy Point Beach and Bruce Gabrielson's Surf Art Gallery and Museum are located nearby.

Kitchen

Washer

Holiday Inn Express Waldorf by IHG

11370 Days Ct, Waldorf, MD

Free cancellation

CA $149

CA $165 total

includes taxes & fees

13 Apr - 14 Apr

Book a stay at this business-friendly hotel in Waldorf. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Waldorf Marketplace and St. Charles Towne Center are located nearby.

Pool

Breakfast included

Sonesta ES Suites Annapolis

170 Admiral Cochrane Dr, Edgewater, MD

Free cancellation

Reserve now, pay when you stay

CA $136

CA $155 total

includes taxes & fees

24 Apr - 25 Apr

Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Annapolis Harbor Center Shopping Center and Annapolis Harbour Center are located nearby.

Pool

Breakfast included

SpringHill Suites by Marriott Annapolis

189 Admiral Cochrane Drive, Annapolis, MD

Free cancellation

Reserve now, pay when you stay

CA $133

CA $151 total

includes taxes & fees

6 Apr - 7 Apr

Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Annapolis Harbor Center Shopping Center and Annapolis Harbour Center are located nearby.

Pool

Hot tub

Inn at Perry Cabin

308 Watkins Ln, St. Michaels, MD

CA $638

CA $772 total

includes taxes & fees

31 Mar - 1 Apr

Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Perry Cabin Park and Higgins Yacht Yard and Marina are located nearby.

Pool

Hot tub

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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.

Popular places to visit

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.

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.

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.

Chesapeake Beach Vacations

Experiencing the true essence of Chesapeake Beach begins with brushing up on a few basic things. Are you ready to find out just where this unique place is and what there is to do there?

To help you get your bearings, Chesapeake Beach is 30 miles (48 kilometers) southeast of the noteworthy city of Washington.

6,000 friendly locals live in this part of Western Shore of Maryland.

Hotels in Chesapeake Beach

You'll have to act quickly if you want to stay as close as possible to Chesapeake Beach. The Chesapeake Beach Resort And Spa is the only listed property within a short commute of the center.

Places to visit in Chesapeake Beach

From the huffing, puffing locomotives of the past to the sleek and luxurious trains of today, rail transport has captivated people for generations. Learn all about the transformation of these grand machines at Chesapeake Beach Railway Museum. Want some more options? We hope you brought your swimsuit! No matter if you prefer stomach-flipping water slides, cruising down lazy rivers or relaxing in paddling pools, Chesapeake Beach Water Park offers a fun day out for everyone. And that's not all there is. Abandon your history journals! Witness the past jump to life at Bayside History Museum.

Where do you fly into for Chesapeake Beach?

There's no better feeling than finally arriving in a new place. If you're hopping on a flight to Chesapeake Beach, chances are you'll fly into Ronald Reagan Washington National Airport (DCA). It's approximately 30 miles (48 kilometers) to the west of the central area. Collect your luggage and get set to kick-start your vacation!

Frequently asked questions

How much are vacation packages to Chesapeake Beach?

Your vacation dreams can come true in Chesapeake Beach for as low as CA $748. Package deals include flights and hotels, and they’ll make your booking a breeze. All you’ll have to concentrate on is getting out there and having a great time.

How long should my Chesapeake Beach vacation be?

Your Chesapeake Beach break can be as long or as short as you would like it to be, but the majority of people stay roughly 2 nights. Eager to veer off the beaten path and uncover some lesser-known sights? Lock in a few extra nights and experience another side of this destination.

Where can I get the best vacation package deals for Chesapeake Beach?

You’ll discover an amazing range of Chesapeake Beach package deals on Travelocity. With 400 airlines and 1,000,000 properties around the globe, putting together the ultimate escape will be a piece of cake.

Why should I purchase my Chesapeake Beach vacation bundle via Travelocity?

With our Price Match Guarantee, we’ll match any lower price you’re able to find. Add on our 24/7 support and superb service and the vacation of your dreams is closer than ever before.

Will I save money on my Chesapeake Beach car rental if I bundle it with hotels and flights?

You certainly can — combine your hotel, car and flight into a Chesapeake Beach vacation package and you’ll save a tidy sum. With so much to see in and around Chesapeake Beach, that rental vehicle will make it easy to explore. Once you’ve slid into the driver’s seat, hit the wide open road and make your way to Liberty Bell Center, a famous sight around 177 kilometers from Chesapeake Beach.

Which airport is best for Chesapeake Beach?

Many travelers fly into Ronald Reagan Washington National Airport (DCA), 48 kilometers west of downtown Chesapeake Beach. Others prefer Washington Dulles Intl. Airport (IAD) (80 kilometers away from central Chesapeake Beach) or Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (56 kilometers away from central Chesapeake Beach).

What is there to do in Chesapeake Beach?

While getting off the beaten track can be rewarding, you shouldn’t miss the big-name attractions that make a place famous. Breezy Point Beach and Chesapeake Beach Water Park are a couple of them in Chesapeake Beach.

Where should I stay when visiting Chesapeake Beach?

The Rod N Reel Resort is the number one choice of many travelers. Book now before it’s too late.