Dorchester County Vacation Packages 2026 from $331

Search vacation packages deals in Dorchester County's top destinations

Cambridge

Vacations

Dorchester County flight + hotel vacation packages

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

Renaissance Baltimore Harborplace Hotel

Inner Harbor

Save 100% on your flight

$331

per person

Jun 18 - Jun 22

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a gym on site, and laundry facilities and concierge services are also offered.

The Westin DC Downtown

Downtown Washington D.C.

Save 100% on your flight

$399

per person

Jun 12 - Jun 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

This smoke-free hotel features 5 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and a garden are also offered.

Kellogg Conference Hotel at Gallaudet University

Northeast

Save 100% on your flight

$397

per person

Jun 18 - Jun 21

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.

Lyle Washington D.C.

Northwest

$380

per person

May 18 - May 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a garden are also offered.

Graduate by Hilton Annapolis

Save 100% on your flight

$894

per person

May 21 - May 23

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

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

Top Dorchester County hotels deals

Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD

Free Cancellation

Reserve now, pay when you stay

$262 nightly

$297 total

Apr 28 - Apr 29

Total with taxes and fees

This smoke-free resort features a private beach, a golf course, and a full-service spa. Bring the family and enjoy the children's club, mini golf, and children's pool. Enjoy the 2 outdoor pools and perks like free self parking and free WiFi.

On private beach

Pool

Days Inn & Suites by Wyndham Cambridge

2917 Ocean Gateway Cambridge MD

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$84 total

Apr 16 - Apr 17

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 24-hour business center and onsite conference space. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

Comfort Inn & Suites Cambridge

2936 Ocean Gtwy Cambridge MD

Free Cancellation

$118 nightly

$131 total

May 5 - May 6

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. 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.

Pool

Breakfast included

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge MD

Get rates

An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Pool

Kitchen

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD

Free Cancellation

Reserve now, pay when you stay

$153 nightly

$168 total

Apr 27 - Apr 28

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

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

$572 nightly

$629 total

Apr 23 - Apr 24

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.

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Frequently asked questions

How much are vacation packages to Dorchester County?

Travelocity has package deals to Dorchester County, as well as flights and hotels, starting from as low as $331. With all that extra cash, you could book some popular tours or perhaps even add on a couple of extra days to your adventure.

Where can I get the best vacation package deals for Dorchester County?

You can lock in sensational Dorchester County package deals with Travelocity. Choose from 400 airlines and 1,000,000 worldwide properties and turn those travel dreams into a reality.

Why should I purchase my Dorchester County vacation package via Travelocity?

We've got destinations and experiences to suit every kind of traveler, top-notch service and support available 24/7. On top of that, we'll match any better price you happen to find with our Price Match Guarantee.

Can I save on my Dorchester County car rental if I combine it with my hotel or flight?

Bundling your bookings into a Dorchester County vacation package will certainly save you money. You can combine a car and flight; a flight, car and hotel; or a hotel and car. You won't find a better way to explore the greater Dorchester County region than from behind the wheel of your own rental car. You can also add activities and experiences to your Travelocity package.

Which airport is best for Dorchester County?

Ronald Reagan Washington National Airport (DCA) is a popular option for those flying to Dorchester County. Baltimore Washington Intl. Thurgood Marshall Airport (BWI) and Salisbury - Ocean City Wicomico Regional Airport (SBY) also welcome many of the region's flights.

What is there to do in Dorchester County?

A diverse and lively destination, Dorchester County boasts some excellent sights and attractions. Layton's Chance Vineyard and Winery and Elliott Island are among the most renowned here.