Princess Anne Vacation Packages 2026 from $306

Princess Anne flight + hotel vacation packages

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

Country Inn & Suites by Radisson, Salisbury, MD

Save 100% on your flight

$306

per person

Sep 24 - Sep 27

found 19 hours ago

Roundtrip flight included

Orlando (MCO) to Salisbury (SBY)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Fenwick Shores, Tapestry Collection by Hilton

Save 100% on your flight

$1,172

per person

Sep 24 - Sep 27

found 19 hours ago

Roundtrip flight included

Orlando (MCO) to Salisbury (SBY)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Comfort Inn Gold Coast

North Ocean City

Save 100% on your flight

$443

per person

Sep 24 - Sep 27

found 19 hours ago

Roundtrip flight included

Orlando (MCO) to Salisbury (SBY)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Enjoy the hot tub and perks like free self parking and free WiFi. A terrace, a garden, and a grocery/convenience store are also on offer.

Gold Leaf Hotel of Dewey - Rehoboth Beach

Save 100% on your flight

$363

per person

Sep 24 - Sep 27

found 19 hours ago

Roundtrip flight included

Orlando (MCO) to Salisbury (SBY)

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Free self parking, laundry facilities, and free newspapers are also on offer.

Boardwalk One

Downtown Ocean City

Save 100% on your flight

$637

per person

Aug 21 - Aug 24

found 14 hours ago

Roundtrip flight included

Orlando (ORL) to Salisbury (SBY)

This aparthotel features a seasonal outdoor pool and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning and laundry facilities are also provided.

Top Princess Anne hotels deals

Econo Lodge Princess Anne

10936 Market Lane US 13 Princess Anne MD

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$90 total

Jul 19 - Jul 20

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pool

Breakfast included

Americas Best Value Inn Princess Anne

30359 Mt. Vernon Road Princess Anne MD

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$83 total

Jul 13 - Jul 14

Total with taxes and fees

Free WiFi in public areas is available at this motel.

Pet friendly

Free WiFi

Chincoteague Inn

4417 Deep Hole Road Chincoteague VA

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$145 total

Jul 13 - Jul 14

Total with taxes and fees

An outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area is also provided.

Pool

Parking included

Blufin Bungalows & Marina

2477 Main St Chincoteague VA

Get rates

A seasonal outdoor pool is featured at this vacation home, along with free self parking. WiFi in public areas is free. A convenience store is also provided.

Pool

Kitchen

Wingate by Wyndham Salisbury MD Airport North

406 Punkin Ct Salisbury MD

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$121 total

Jul 19 - Jul 20

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 express check-out. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Parking included

Key West Cottages

4251 Main Street Chincoteague VA

$341 nightly

$383 total

Aug 4 - Aug 5

Total with taxes and fees

A private beach and an outdoor pool are featured at this smoke-free cottage. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A terrace, a snack bar/deli, and a picnic area are also on offer.

Pool

Kitchen

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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.

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.

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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 $306. 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.