A sunset over a lake with a dock and a small settlement.

Princess Anne Vacations from $213

Book a Hotel + Flight or Car together to unlock savings

Your Princess Anne Vacation

Well known for its rich history and coastal scenery, Princess Anne is a fabulous getaway destination. Lock in one of our Princess Anne vacation packages and enjoy all that this lively city has to offer. If some sightseeing is on your list of things to do during your trip to Princess Anne, check out major attractions like University of Maryland Eastern Shore. A couple of quick clicks is all it takes to put together the ideal Princess Anne vacation on Expedia.

The Latest Princess Anne Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 30 - Feb 2

    Grand Hotel Ocean City Oceanfront + Flight

    Downtown Ocean City
    3 nights
    3.0 star property
    9.0/10 - Wonderful (4,013 reviews)
    "Cool"
    Reviewed November 15, 2026
    Roundtrip • San Juan (SJU) - Salisbury (SBY)
    SJU - PHL • Nonstop PHL - SJU • Nonstop
    $289
    $213
    per traveler
    found 1 day ago
    Grand Hotel Ocean City Oceanfront
  • Jan 30 - Feb 2

    Oceanic Motel + Flight

    Downtown Ocean City
    3 nights
    2.0 star property
    7.0/10 - Good (851 reviews)
    Roundtrip • San Juan (SJU) - Salisbury (SBY)
    SJU - SBY • 1 stop SBY - SJU • 1 stop
    $2,176
    $1,659
    per traveler
    found 12 hours ago
    Oceanic Motel
  • Jan 30 - Feb 2

    Hyatt Place Ocean City / Oceanfront + Flight

    Downtown Ocean City
    3 nights
    3.0 star property
    9.0/10 - Wonderful (1,874 reviews)
    Roundtrip • San Juan (SJU) - Salisbury (SBY)
    SJU - PHL • Nonstop PHL - SJU • Nonstop
    $309
    $244
    per traveler
    found 1 day ago
    Hyatt Place Ocean City / Oceanfront
  • Jan 30 - Feb 2

    Sea Bay Hotel + Flight

    Midtown Ocean City
    3 nights
    2.5 star property
    8.2/10 - Very good (735 reviews)
    Roundtrip • San Juan (SJU) - Salisbury (SBY)
    SJU - SBY • 1 stop SBY - SJU • 1 stop
    $2,193
    $1,773
    per traveler
    found 12 hours ago
    Sea Bay Hotel
  • Jan 30 - Feb 2

    Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel + Flight

    North Ocean City
    3 nights
    3.5 star property
    8.2/10 - Very good (2,024 reviews)
    Roundtrip • San Juan (SJU) - Salisbury (SBY)
    SJU - SBY • 1 stop SBY - SJU • 1 stop
    $1,484
    $1,208
    per traveler
    found 12 hours ago
    Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Where to stay in and around Princess Anne

In Princess Anne, United States, explore the charm of Somerset Avenue and the vibrant city center, perfect for family-friendly outings. Nearby, Wight Bay offers scenic views and outdoor adventures, making it an ideal destination for culture and relaxation. Enjoy a unique blend of experiences during your stay!

Salisbury

Discover Salisbury, a vibrant city ideal for travelers seeking a blend of adventure, education, and family fun. With attractions like Salisbury University and the Wicomico Youth and Civic Center, visitors can enjoy cultural events and entertainment, while nearby beaches offer outdoor relaxation. Located about 12 miles by car from Princess Anne, Salisbury provides easy access to a variety of experiences, making it a smart choice for your next getaway.

Westover

Experience the charm of Westover, an excellent hub for family and nature enthusiasts eager to explore the beautiful bay, inviting beaches, and scenic urban parks. With attractions like the historic University of Maryland Eastern Shore, the engaging Delmarva Discovery Center, and the relaxing Upper Hill Park, Westover offers a delightful blend of education and recreation. Located about 6 miles by car from Princess Anne, this welcoming area is a smart choice for your next vacation.

Mount Vernon

If you are a family traveler or someone seeking outdoor adventures, look no further than Mount Vernon in Princess Anne, Maryland. This charming village offers a delightful mix of experiences, from the scenic Mount Vernon Beach to the lush nature reserve and the engaging activities at the University of Maryland Eastern Shore. With a blend of cultural and recreational attractions, Mount Vernon is a prime choice for your stay, providing easy access to beautiful landscapes and family-friendly fun.

Eden

Eden stands out as a prime spot for travelers interested in family-friendly activities and nature retreats. With its proximity to popular attractions like Salisbury University, Wicomico Youth and Civic Center, and the scenic family beach, visitors can easily immerse themselves in a mix of education, entertainment, and outdoor fun. Located about 6 miles by car from Princess Anne, Eden offers a smart choice for your stay, providing access to a vibrant local culture and beautiful surroundings.

Whitehaven

Travelers visiting the area often choose Whitehaven, especially families and nature enthusiasts seeking close proximity to captivating outdoor experiences. This charming village offers easy access to the historic University of Maryland Eastern Shore, the scenic Mount Vernon Park, and the inviting Mount Vernon Beach, making it a great spot for relaxation and exploration. Located about 7 miles by car from Princess Anne, Whitehaven is a smart choice for those looking to enjoy a budget-friendly getaway in a picturesque setting.

Discover the most popular places to visit in Princess Anne

Princess Anne Hotel Deals

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.

Frequently Asked Questions

What's included in a Princess Anne vacation package?

A Princess Anne vacation package typically bundles round-trip flights, your hotel stay, and a rental car. Nearly all hotels in Princess Anne fall into the budget tier, offering great value. Some hotels, like Americas Best Value Inn Princess Anne, provide amenities such as air conditioning, free breakfast, and free WiFi, and are also pet friendly. Flights often arrive at Washington, DC (DCA-Ronald Reagan Washington National), about 85 miles away.


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a Princess Anne vacation package?

When you bundle, you can save up to 30%*. To save money on a Princess Anne package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's the best vacation package for Princess Anne?

For travelers seeking the best vacation packages in Princess Anne that offer great value, consider a stay at Americas Best Value Inn Princess Anne. This hotel is located about 1 mile from central Princess Anne and about a 10-minute walk from Princess Anne Town Hall. It provides essential amenities like air conditioning, free breakfast, free WiFi, and it is also pet friendly, making it a convenient base for exploring the outdoor and nature attractions of the area.

Is Princess Anne better suited for a beach vacation or a cultural trip?

Princess Anne is primarily an outdoor and nature destination, offering a rich historical experience alongside its natural scenery. The town is home to the Princess Anne Historic District, featuring about 150 acres of preserved architectural heritage, including the notable Teackle Mansion.


For those seeking a coastal experience, Mount Vernon Beach is about 16 miles from central Princess Anne, providing a place to enjoy the water. A Princess Anne vacation can therefore blend historical exploration with outdoor activities and beach visits.

What are the top things to do in Princess Anne?

A Princess Anne vacation offers a blend of historical exploration and natural beauty. Here are some top things to do:


Browse and book things to do in Princess Anne on Expedia.

Do you need to rent a car in Princess Anne, or is public transport enough?

For a Princess Anne vacation package, renting a car is generally recommended for getting around, especially if you plan to explore beyond the immediate town center. While Princess Anne is a small and walkable town, with bike lanes along Somerset Avenue for cycling, many attractions are spread out.


A car provides the most flexibility to reach places like Mount Vernon Beach, about 16 miles away, or the Delmarva Discovery Center, about 14 miles from central Princess Anne. For arrivals, major airports like Washington, DC (DCA-Ronald Reagan Washington National) are about 85 miles away, making a rental car or pre-arranged transport essential for your Princess Anne vacation packages with flights.

Are Princess Anne vacation package hotels conveniently located?

Princess Anne vacation package hotels are conveniently located, with options close to the town center.


For example, Americas Best Value Inn Princess Anne is situated about 1 mile from central Princess Anne, placing you within easy reach of local attractions. This makes it simple to explore the area during your Princess Anne vacation package.

Can I change or cancel my Princess Anne vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Princess Anne vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Princess Anne vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Princess Anne vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Princess Anne?

To find last-minute vacation packages to Princess Anne, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Princess Anne vacation packages?

Free cancellation on a Princess Anne vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Princess Anne vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Princess Anne getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Princess Anne vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.