Princess Anne Vacations from $434

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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.
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

$434
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
7.2/10 Good! (470 reviews)
Location, didn't clean room everyday.

Reviewed on Aug 15, 2026

Beach Walk

Beach Walk

Downtown Ocean City
Save 100% on your flight
$1,616
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.6/10 Good! (107 reviews)
An older hotel but very convenient located.

Reviewed on Aug 11, 2026

Sea Bay Hotel

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

Plim Plaza Hotel

Plim Plaza Hotel

Downtown Ocean City
$1,368
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
7.4/10 Good! (1,109 reviews)
Best customer service room was very clean.

Reviewed on Aug 16, 2026

White Marlin Inn

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

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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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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.
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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.
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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.
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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.
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Ballards Island

Commune with nature and explore the great outdoors at Ballards Island during your travels in Mount Vernon.
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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.
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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.
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Princess Anne Hotel Deals

Econo Lodge Princess Anne

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

Econo Lodge Princess Anne
Americas Best Value Inn Princess Anne

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
Americas Best Value Inn Princess Anne
Chincoteague Inn

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
Chincoteague Inn
See all 844 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

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.

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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.