Princess Anne Vacations from $1,519
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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.
Majestic Hotel & Apartments
Downtown Ocean City
$1,707
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
5.8/10 (475 reviews)
Bed bugs on the couch my younger brother started getting trail bites and decided to sleep on the floor the rest of the time there
Reviewed on Aug 24, 2026
Miramar Condominiums
Downtown Ocean City
$2,313
per person
Sep 30 - Oct 4
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
9.4/10 Exceptional! (26 reviews)
Very convenient location, helpful staff. The unit itself (#504) could use some updating. The carpeting is loose/has big wrinkles in it and the living room furniture is not very comfortable. The mattress in the sofa sleeper is well past its prime. There was a foam topper on it which helped a little, but it’s not very comfortable. The king mattress is also in need of replacement. Overall, the condo fit our needs very well for our ocean city stay. Please note that there are very limited supplies at the condo (paper towel, shampoo, etc), so plan to bring shampoo, condition, something to clean the kitchen counters with, etc. if you plan to use the dishwasher more than twice or the washer more than twice you will need to bring detergent.
Reviewed on Aug 19, 2026
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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.
Mount Vernon Park
This peaceful 9.6-acre park offers scenic trails through lush greenery for walking and hiking enthusiasts. Families can enjoy the playground and baseball field while experiencing a tranquil escape in Princess Anne.
Princess Anne Town Hall
This historic municipal building serves as the heart of Princess Anne's local government and community affairs. Visit during the monthly town meetings to experience small-town democracy in action.
Mount Vernon Beach
Why not spend a lazy afternoon at Mount Vernon Beach during your trip to Mount Vernon?
Manokin Historic District
This historic district showcases exceptional Federal and Victorian architecture from the 18th to early 20th century. Stroll tree-lined streets to admire Teackle Mansion and other preserved buildings.
Somerset County Library
This community cornerstone offers an extensive collection of books, digital resources, and programs for all ages. Browse the shelves, use the free computers, or attend seasonal events in this welcoming space.
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.
Manokin Park
Manokin Park offers a peaceful riverside retreat with shaded picnic areas and a kayak launch along the Manokin River. Check tide schedules before planning water activities to avoid muddy conditions.
Princess Anne Hotel Deals
Econo Lodge Princess Anne
10936 Market Lane US 13 Princess Anne MD
$72 nightly
$80 total
Sep 15 - Sep 16
Total with taxes and fees
6.6/10 (709 reviews)
"It was myself and my two grandsons(11&7). We stayed for the night. Hotel was dated which was fine. They had 3)4 sheds in the back that had junk piled up in the sides. We arrived at 11pm. I asked if they had late check out and how much it cost. The attendant said late check out is at 11:30am ( normal ..."
Reviewed on Aug 21, 2026
Americas Best Value Inn Princess Anne
30359 Mt. Vernon Road Princess Anne MD
Fully refundableReserve now, pay when you stay
$75 nightly
$83 total
Aug 26 - Aug 27
Total with taxes and fees
7/10 Good! (74 reviews)
"Very pleasant stay look forward to staying again"
Reviewed on Aug 20, 2026
Chincoteague Inn
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
$109 nightly
$122 total
Sep 7 - Sep 8
Total with taxes and 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.
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
How much does a Princess Anne vacation package cost?
You'll find cheap prices from $1,519 on Expedia for your Princess Anne break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Princess Anne costs.
What are the cheapest months to go to Princess Anne?
December, January and February are the best times to look for cheap Princess Anne vacation packages. Traveling in quieter months means you can typically find better prices on hotels and flights.
How many days is enough for Princess Anne?
The ideal length for your Princess Anne vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to visit all the main attractions and discover some hidden treasures along the way.
How to find the best Princess Anne package deals?
Start your search for a Princess Anne package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Princess Anne package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Princess Anne adventure off to a flying start.
Is it cheaper to book a Princess Anne vacation as a package?
You can enjoy significant savings on your next Princess Anne retreat by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Princess Anne?
If you're considering a spontaneous Princess Anne vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Princess Anne vacation packages?
Your Princess Anne trip should be a relaxing escape from your busy life, not a reason for money worries. So to allow you a bit more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
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- Visit Princess Anne
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- Cypress Park
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- Salisbury University
- Furnace Town Living Hertiage Museum
- Maryland Beach
- Harriet Tubman Underground Railroad National Historical Park
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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.
