Princess Anne Vacation Packages 2026 from $264

Princess Anne flight + hotel vacation packages

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

Red Roof Inn & Suites Chestertown

$264

per person

Nov 13 - Nov 15

found 10 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Salisbury (SBY)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A lobby fireplace, laundry facilities, and free newspapers are also on offer.

Comfort Inn & Suites Chestertown

$331

per person

Nov 13 - Nov 15

found 10 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Salisbury (SBY)

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

The Lodge at Great Oak Landing

$287

per person

Nov 13 - Nov 15

found 10 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Salisbury (SBY)

A golf course, 2 restaurants, and a 24-hour gym are all featured at this smoke-free lodge. Dine at the beachfront restaurant and relax with sun loungers. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

St Michaels Inn

$514

per person

Oct 9 - Oct 12

found 3 hours ago

Roundtrip flight included

Dallas (DFW) to Salisbury (SBY)

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.

Hilton Garden Inn Kent Island Marina

$958

per person

Oct 9 - Oct 12

found 3 hours ago

Roundtrip flight included

Dallas (DFW) to Salisbury (SBY)

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. Enjoy the gym and perks like free self parking.

Stay near popular Princess Anne attractions

University of Maryland Eastern Shore

8.4/10 (90 reviews)

Explore the campus of University of Maryland Eastern Shore, during your travels in Princess Anne. Wander the seaside and beaches in the area.

See properties

Frequently asked questions

How much are vacation packages to Princess Anne?

With a Travelocity vacation package, you can be living it up in Princess Anne for as low as $264. Flights, tours and hotels — we've got you. You can save some cash just for bundling your bookings. And with all that taken care of before you go, you can sit back, relax and enjoy the adventure.

How long should my Princess Anne vacation be?

There are no firm rules for how long your Princess Anne vacation should be, but the majority of people stay for around 2 nights. Got some leeway with your departure date? Consider extending your trip by a few more nights. Then you'll have loads of time to explore the area's hidden treasures too.

Where can I get the best vacation package deals for Princess Anne?

Find your dream escape at Travelocity. With access to 400 airlines and an impressive 1,000,000 properties across the globe, finding the perfect Princess Anne package deal couldn't be simpler.

Why should I purchase my Princess Anne vacation bundle with Travelocity?

Because life is one amazing journey, and we offer everything you need to help you along the way. With our top-quality service and Price Match Guarantee, you can organize your trip with confidence. What's more, you can rest easy while you're away knowing we're always available to chat via our 24/7 customer support.

Will I save money on my Princess Anne car rental if I bundle it with my hotel or flight?

You certainly can — bundle your car, hotel and flight into a Princess Anne vacation package and you'll save a tidy sum. With so much to see and do in the Princess Anne area, that rental vehicle will make exploring easy. Once you've settled into the driver's seat, crank up the tunes and make tracks to White House, a well-known sight roughly 85 mi from Princess Anne.

Which airport is best for Princess Anne?

The main airport is Salisbury - Ocean City Wicomico Regional Airport (SBY), roughly 14 mi northeast of inner Princess Anne.

Where should I stay when visiting Princess Anne?

If you're looking for a place to base yourself, consider the Washington Inn And Tavern. It's the top pick for many visitors.