Princess Anne Vacations from $548

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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.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $599, price is now $548 per person
$548
per person
Dec 10 - Dec 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
9/10 Wonderful! (3,964 reviews)

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $871, price is now $763 per person
$763
per person
Dec 10 - Dec 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
9.4/10 Exceptional! (34 reviews)

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $729, price is now $652 per person
$652
per person
Jan 21 - Jan 24
found 20 hours ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
9.4/10 Exceptional! (874 reviews)

Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

3 out of 5
North Ocean City
Price was $645, price is now $593 per person
$593
per person
Dec 10 - Dec 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
7.8/10 Good! (1,474 reviews)
Friendly staff

Reviewed on Oct 29, 2026

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Stay near popular Princess Anne attractions

University of Maryland Eastern Shore

8.4/10 (90 reviews)
Founded in 1886, UMES is a historically black land-grant university with a picturesque campus in Princess Anne. Visitors can explore the historic architecture and vibrant academic culture through guided tours.
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Princess Anne Hotel Deals

Econo Lodge Princess Anne

Econo Lodge Princess Anne

2 out of 5
10936 Market Lane US 13 Princess Anne MD
$72 nightly
The price is $80 total per night from Nov 19 to Nov 20
$80 total
Nov 19 - Nov 20
Total with taxes and fees
Econo Lodge Princess Anne
Americas Best Value Inn Princess Anne

Americas Best Value Inn Princess Anne

2 out of 5
30359 Mt. Vernon Road Princess Anne MD
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $78 total per night from Oct 30 to Oct 31
$78 total
Oct 30 - Oct 31
Total with taxes and fees
Americas Best Value Inn Princess Anne
Best Western Salisbury Plaza

Best Western Salisbury Plaza

2.5 out of 5
1735 N Salisbury Blvd Salisbury MD
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $96 total per night from Nov 1 to Nov 2
$96 total
Nov 1 - Nov 2
Total with taxes and fees
Best Western Salisbury Plaza
See all 841 properties in Princess Anne
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.

Find the Best Princess Anne Vacation Packages

Princess Anne Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Salisbury - Ocean City Wicomico Regional Airport (SBY)
Population
3,300
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
University of Maryland Eastern Shore and Great Hope Golf Course

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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.

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