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.
Fenwick Shores, Tapestry Collection by Hilton
CA $1,547
per person
Oct 4 - Oct 11
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
9.4/10 Exceptional! (809 reviews)
Pool was small and staff were running up and down the floors to get drinks. Ken seemed to be doing everything. Staff at the front desk was bi-polar. Some were very nice and others acted like they didn’t want to be there and were very rude.
Reviewed on Aug 9, 2026
Hotel Monte Carlo Ocean City
Downtown Ocean City
CA $1,563
per person
Oct 4 - Oct 11
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
7.8/10 Good! (1,017 reviews)
It was right at the Boardwalk was a good thing, but the bad thing is when I got there my room air conditioning wasn’t working right. I called to the desk to report it. The maintenance guy came to my room the next aftenoon, after I had to report it again. They changed my room to another room where the air-conditioning kept cutting off and making humming noises. Had a very hot stay. Thursday night the lady said she would try to get me done feedback. Could I speak to someone from Expedia. My number is 1 267 679-4303 thank you
Reviewed on Aug 9, 2026
Americana Motor Inn
Downtown Ocean City
CA $1,470
per person
Oct 4 - Oct 11
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
8.4/10 Very good! (1,002 reviews)
Everything was great besides the parking lot per usual. A narrow a small set up (during peak season)
Reviewed on Aug 11, 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
CA $107
CA $118 total
Sep 7 - Sep 8
includes taxes & fees
Americas Best Value Inn Princess Anne
30359 Mt. Vernon Road Princess Anne MD
Fully refundableReserve now, pay when you stay
CA $105
CA $116 total
Aug 12 - Aug 13
includes taxes & fees
6.8/10 (68 reviews)
"I am over 65 years old and have traveled all over the United States and over seas, and have stayed in over 300 hotels in all my years I have never seen a dump of a hotel as this one. If I could give a rating of Zero I would. There was no working phones in the rooms, no hair dryer, air conditioner ..."
Reviewed on Aug 3, 2026
Chincoteague Inn
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
CA $138
CA $155 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
"Clean, safe, walkable to shops & restaurants, the a/c was excellent"
Reviewed on Aug 10, 2026
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?
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.
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.
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.
Manokin Historic District
You can find out about the history of Princess Anne with a trip to Manokin Historic District. You can enjoy the restaurants while in the area.
Wellington State Wildlife Management Area
Explore the great outdoors at Wellington State Wildlife Management Area, a lovely green space in 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 $1,335 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.
