Princess Anne Vacations from $434
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Sea Bay Hotel
Midtown Ocean City
$1,835
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
8.2/10 Very Good! (632 reviews)
Had to ask to have my room cleaned and bed made. Was done one time during my 4 night stay. Did not know if that is the norm, but would have been helpful to have known in advance.
Reviewed on Aug 14, 2026
White Marlin Inn
Downtown Ocean City
$783
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
5.2/10 (54 reviews)
Ugh little rooms for the price BUT THE CLEANLINESS LOL-the parking lot had stuff all through it/garbage/dirty towels/the mirror in our bathroom was so dirty I went and told the manager at front desk-and his reply was “Do you want glass cleaner!!??” Umm NO-you adding me to payroll!!?? It was so bad will never go back
Reviewed on Aug 15, 2026
Don't see what you're looking for?
See all available trips from Columbus to Princess Anne
View all tripsStay 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.
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.
Hytche athletic Center
6.0/10 (1 review)
The Hytche Athletic Center serves as the 5,500-seat home court for UMES Hawks basketball and volleyball teams. Catch the collegiate energy during basketball season while enjoying the recently renovated facilities.
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.
Ballards Island
Commune with nature and explore the great outdoors at Ballards Island during your travels in 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.
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.
Princess Anne Hotel Deals
Econo Lodge Princess Anne
10936 Market Lane US 13 Princess Anne MD
Fully refundable
$72 nightly
$80 total
Sep 13 - Sep 14
Total with taxes and fees
6.6/10 (707 reviews)
"No comments. It was okay for a 12 hour stay."
Reviewed on Aug 12, 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 17 - Aug 18
Total with taxes and fees
Chincoteague Inn
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
$99 nightly
$111 total
Sep 13 - Sep 14
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 |
More vacations you might like
Frequently asked questions
How much does a Princess Anne vacation package cost?
You'll find cheap prices from $434 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.
Explore a world of travel with Expedia
- Pocomoke City Hotels
- Cottages in Princess Anne
- B&B in Westover
- Hotels with a Pool in Princess Anne
- Salisbury Hotels
- Ocean City Hotels
- B&B in Princess Anne
- Princess Anne Hotels
- Rv Parks in Westover
- Berlin Hotels
- Hotels with Free Breakfast in Princess Anne
- Cottages in Somerset County
- Beach Hotels in Princess Anne
- Vacation Homes in Westover
- Apartments in Somerset County
- Resorts & Hotels with Spas in Princess Anne
- Cheap Hotels in Westover
- Fruitland Hotels
- 3 Star Hotels in Eden
- Luxury Hotels in Ocean City
- 4 Star Hotels in Princess Anne
- Motels in Princess Anne
- Vacation Homes in Princess Anne
- Oceanfront Hotels in Princess Anne
- Best Western Hotels in Westover
- Eden Hotels
- Cheap Hotels in Ocean City
- Cabin Rentals in Somerset County
- Hotels near University of Maryland Eastern Shore
- Pet-Friendly Hotels in Westover
- Westover Hotels
- Family Hotels in Princess Anne
- Condo Rentals in Princess Anne
- Oceanfront Hotels in Ocean City
- Hotels near Ocean City Boardwalk
- Historic Hotels in Princess Anne
- B&B in Eden
- Houseboats in Princess Anne
- Pet-Friendly Hotels in Princess Anne
- Pet-Friendly Hotels in Ocean City
- Cabin Rentals in Princess Anne
- Condo Rentals in Ocean City
- Cheap Hotels in Salisbury
- 4 Star Hotels in Eden
- Motels in Ocean City
- Cheap Hotels in Princess Anne
- Extended Stay Hotels in Princess Anne
- Luxury Hotels in Princess Anne
- Flights to Westover
- Flights to Salisbury
- Flights from Princess Anne
- Flights from Charlotte (CLT) to Salisbury (SBY)
- Flights from Salisbury - Ocean City Wicomico Regional
- Flights from Boston (BOS) to Salisbury (SBY)
- Flights to Princess Anne
- Flights to Eden
- Flights to Ocean City
- Flights from Baltimore (BWI) to Salisbury (SBY)
- Eden Vacations
- Pocomoke River State Park
- Arthur W. Perdue Stadium
- Coco's Funhouse
- Visit Westover
- Eastern Shore Baseball Hall of Fame Museum
- Bishop's Stock Fine Art
- Wicomico Youth and Civic Center
- Casino at Ocean Downs
- Fruitland Vacations
- Mardela Springs Vacations
- Ocean City Vacations
- Visit Princess Anne
- Salisbury Zoo
- Museum of Eastern Shore Culture at Salisbury University
- Visit Salisbury
- Visit Eden
- Pemberton Historical Park
- Poplar Hill Mansion
- Julia A. Purnell Museum
- Cypress Park
- Salisbury Vacations
- Salisbury University
- Furnace Town Living Hertiage Museum
- Maryland Beach
- Harriet Tubman Underground Railroad National Historical Park
- Coventry Parish Ruins
- Crisfield Vacations
- Deal Island Vacations
- J. Millard Tawes Museum
- Delmar Vacations
- Pocomoke City Vacations
- Ocean City Boardwalk
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
