Princess Anne Vacation Packages
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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.
Top Princess Anne Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront
Downtown Ocean City
CA $1,223
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
9/10 Wonderful! (3,946 reviews)
We found our room to be surprisingly spacious, very clean, and comfortable; however, the kitchenette/bathroom areas were a bit dated. The property location was excellent and there were restaurants and a pool within the property. The common areas inside the hotel and the outdoor space at the front of the hotel were adequate, but guests were somewhat disrespectful, leaving their trash, not replacing chairs after their use, etc... The staff was pleasant enough when checking-in and helpful when we had a question but were ignoring simple tasks like straightening up the common areas when time allowed. Although this was a little off-putting, we would return if the opportunity presented itself.
Reviewed on Oct 19, 2026
Princess Royale Oceanfront Resort
North Ocean City
CA $1,477
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
8.8/10 Excellent! (2,809 reviews)
The property was very clean, staff was awesome and overall the experience was amazing.
Reviewed on Oct 19, 2026
Ready to book your vacation to Princess Anne?
Princess Anne Hotel Deals
Econo Lodge Princess Anne
10936 Market Lane US 13 Princess Anne MD
Fully refundable
CA $102
CA $113 total
Nov 9 - Nov 10
includes taxes & fees
Americas Best Value Inn Princess Anne
30359 Mt. Vernon Road Princess Anne MD
Fully refundableReserve now, pay when you stay
CA $113
CA $126 total
Oct 20 - Oct 21
includes taxes & fees
Best Western Salisbury Plaza
1735 N Salisbury Blvd Salisbury MD
Fully refundableReserve now, pay when you stay
CA $121
CA $135 total
Oct 21 - Oct 22
includes taxes & fees
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.
Mount Vernon Park
Mount Vernon Park is just one of the places to see in Mount Vernon, so why not enjoy the other things to explore during your travels?
Hytche athletic Center
6.0/10 (1 review)
Catch an event at Hytche athletic Center during your trip to Princess Anne. You can enjoy the restaurants while in the area.
Manokin Park
Explore the great outdoors at Manokin Park, a lovely green space in Princess Anne. You can enjoy the restaurants while in the area.
Princess Anne Town Hall
After visiting Princess Anne Town Hall, make a plan to see the other sights and activities in Princess Anne. You can enjoy the restaurants while in the area.
Somerset County Library
After visiting Somerset County Library, make a plan to see the other sights and activities in Princess Anne. You can enjoy the restaurants while in the area.
Ballards Island
Commune with nature and explore the great outdoors at Ballards Island during your travels in Mount Vernon.
Wellingtion Wildlife Management Area
You can take time to visit Wellingtion Wildlife Management Area during your travels to Princess Anne. You can enjoy the restaurants while in the area.
Frequently asked questions
How much does a Princess Anne vacation package cost?
You'll find cheap prices from CA $1,223 on Expedia for your Princess Anne escape. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Princess Anne costs.
What are the cheapest months to go to Princess Anne?
December, January and February are great times to look for cheap Princess Anne vacation packages. Opting to travel in less busy months means you can generally find lower prices on flights and hotels.
How many days is enough for Princess Anne?
Generally, a handful of days is enough to visit the major attractions during your Princess Anne vacation. However, if you prefer to have time to rest or take day tours, consider extending your itinerary.
How to find the best Princess Anne package deals?
Landing a cheap Princess Anne package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Princess Anne package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Princess Anne vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still get the freedom to create a personalized Princess Anne vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Princess Anne?
If you're planning an impromptu Princess Anne trip, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Princess Anne?
- Choose your travel dates: The things you plan to do in Princess Anne and your favourite season will help you decide when to get away.
- Budget wisely: Besides the price of your hotel, you should consider other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that may come up during your trip to Princess Anne.
- Work out your trip length: Consider how long you'd like to spend exploring Princess Anne. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your accommodations and airfare: Once you've settled on your travel dates and duration, book the ideal Princess Anne vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
