Chesapeake Beach Vacation Packages 2025/2026 from $496

Chesapeake Beach flight + hotel vacation packages

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

Kellogg Conference Hotel at Gallaudet University

Northeast

Save 100% on your flight

$496

per person

Nov 9 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.

Kimpton Hotel Monaco Washington DC by IHG

Downtown Washington D.C.

Save 100% on your flight

$839

per person

Dec 15 - Dec 22

just found

Roundtrip non-stop flight included

Dallas (DAL) to Washington (DCA)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, express check-out, and valet parking. A lobby fireplace, WiFi in public areas, and dry cleaning are also on offer.

Homewood Suites by Hilton Arlington Rosslyn Key Bridge

Rosslyn

Save 100% on your flight

$621

per person

Nov 9 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 and free WiFi in public areas. Enjoy freebies like buffet breakfast and an area shuttle

Pentagon Luxe Apartments

Crystal City

Save 100% on your flight

$1,017

per person

Dec 15 - Dec 22

just found

Roundtrip non-stop flight included

Dallas (DAL) to Washington (DCA)

An outdoor pool is featured at this apartment, along with self parking. A communal living room and luggage storage are also provided.

Le Meridien Arlington

Rosslyn

Save 100% on your flight

$846

per person

Dec 15 - Dec 22

just found

Roundtrip non-stop flight included

Dallas (DAL) to Washington (DCA)

This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the business center and WiFi in public areas. There's a gym on site, and laundry facilities and concierge services are also offered.

Top Chesapeake Beach hotels deals

Rod 'N' Reel Resort

4165 Mears Ave, Chesapeake Beach, MD

$159 nightly

$175 total

Oct 13 - Oct 14

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

$104 nightly

$118 total

Oct 30 - Oct 31

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

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$130 total

Oct 19 - Oct 20

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

$92 nightly

$102 total

Oct 7 - Oct 8

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

The Wildset

209 N Talbot St, St. Michaels, MD

$239 nightly

$263 total

Oct 6 - Oct 7

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop, a snack bar/deli, and concierge services are also on offer.

Breakfast included

Pet friendly

Candlewood Suites Annapolis by IHG

1 Womack Dr, Annapolis, MD

Free Cancellation

$97 nightly

$111 total

Oct 6 - Oct 7

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

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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

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.

Frequently asked questions

How much are vacation packages to Chesapeake Beach?

Your vacation dreams can come true in Chesapeake Beach for as low as $496. 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.