Chesapeake Beach Vacation Packages 2025/2026 from $263

Chesapeake Beach flight + hotel vacation packages

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

Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD

$263

per person

Nov 14 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Embassy Suites by Hilton Tysons Corner

$471

per person

Oct 30 - Nov 3

found 1 hour ago

Roundtrip flight included

Chicago (ORD) to Washington (DCA)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the express check-in and WiFi in public areas. Enjoy the 24-hour gym and free buffet breakfast each morning.

Washington Dulles Marriott Suites

$478

per person

Oct 30 - Nov 3

found 1 hour ago

Roundtrip flight included

Chicago (ORD) to Washington (DCA)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-in, and free airport shuttle. Free self parking, a coffee shop, and limo/town car service are also offered.

Lansdowne Resort and Spa

$666

per person

Oct 30 - Nov 3

found 1 hour ago

Roundtrip flight included

Chicago (ORD) to Washington (DCA)

This smoke-free resort features a golf course, 3 outdoor tennis courts, and a restaurant. There's fun for all ages with a waterslide and a playground, and families will appreciate the onsite laundry facilities. Traveling on business? Take advantage of the business center, laundry service, and airport shuttle.

Hampton Inn & Suites Washington-Dulles International Airport

$359

per person

Oct 30 - Nov 3

found 1 hour ago

Roundtrip flight included

Chicago (ORD) to Washington (DCA)

This hotel features an indoor pool and a gym. Free perks include buffet breakfast, free self parking, and a roundtrip airport shuttle. A 24-hour business center, free WiFi in public areas, and a snack bar/deli are also on offer.

Top Chesapeake Beach hotels deals

Rod 'N' Reel Resort

4165 Mears Ave, Chesapeake Beach, MD

Free Cancellation

Reserve now, pay when you stay

$156 nightly

$172 total

Sep 16 - Sep 17

Total with taxes and fees

A marina, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Make the most of the 24-hour gym and seasonal outdoor pool, and relax with drinks at one of the 2 bars/lounges.

Pool

Spa

Sonesta ES Suites Annapolis

170 Admiral Cochrane Dr, Edgewater, MD

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$124 total

Sep 14 - Sep 15

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Pool

Breakfast included

SpringHill Suites by Marriott Annapolis

189 Admiral Cochrane Drive, Annapolis, MD

$110 nightly

$125 total

Sep 16 - Sep 17

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free self-serve breakfast each morning.

Pool

Hot Tub

St Michaels Inn

1228 S Talbot Street, St. Michaels, MD

$89 nightly

$98 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the conference center and conference space on site. Enjoy the seasonal outdoor pool and conveniences like a terrace and laundry facilities.

Pool

Breakfast included

Candlewood Suites Annapolis by IHG

1 Womack Dr, Annapolis, MD

Free Cancellation

$97 nightly

$111 total

Sep 15 - Sep 16

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and laundry facilities and barbecue grills are also offered.

Pet friendly

Parking included

Inn at Perry Cabin

308 Watkins Ln, St. Michaels, MD

$594 nightly

$653 total

Oct 1 - Oct 2

Total with taxes and fees

This luxury hotel features a golf course, a full-service spa, and a marina. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room childcare. Enjoy the 3 outdoor tennis courts and perks like free valet parking and free WiFi.

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

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.

Breezy Point Beach

4.5/5(10 reviews)

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

4.5/5(3 reviews)

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.

Frequently asked questions

How much are vacation packages to Chesapeake Beach?

Your vacation dreams can come true in Chesapeake Beach for as low as $263. 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 110 mi from Chesapeake Beach.

Which airport is best for Chesapeake Beach?

Many travelers fly into Ronald Reagan Washington National Airport (DCA), 30 mi west of downtown Chesapeake Beach. Others prefer Washington Dulles Intl. Airport (IAD) (50 mi away from central Chesapeake Beach) or Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (35 mi 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.