Princess Anne Vacations from $936

Book a Hotel + Flight or Car together to unlock savings

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.
Sahara Motel

Sahara Motel

2.5 out of 5
Downtown Ocean City
Price was $1,456, price is now $936 per person
$936
per person
Sep 18 - Sep 21
found 16 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
7.8/10 Good! (679 reviews)
Room was clean overall

Reviewed on Jul 29, 2026

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Price was $1,562, price is now $996 per person
$996
per person
Sep 18 - Sep 21
found 16 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
7.8/10 Good! (40 reviews)
For what I paid it wasn’t worth it. I should get money back. Some of the blinds were broken and the one bedroom window didn’t have one at all. Told the manager but no one came to install one. Nothing like the picture. Our full bed the frame was broken. The can opener should be thrown away filthy. The cleaning staff was very accommodating though. Don’t STAY THERE .

Reviewed on Jul 22, 2026

Empress Motel

Empress Motel

2 out of 5
Downtown Ocean City
Price was $1,474, price is now $941 per person
$941
per person
Sep 18 - Sep 21
found 16 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
7.8/10 Good! (175 reviews)
We stayed there last year and the ice machine was broke, went back this year and it was still broke. They were sending us all over the place to get ice, simply ridiculous The tub was clogged and then at 4:30 in the afternoon we had no clean towels, had to track down a maid for them Our last night there we had the police at the hotel 2 times, the second time there were 6 police officers there Never again!!!

Reviewed on Jul 27, 2026

Seabonay Oceanfront Motel

Seabonay Oceanfront Motel

2 out of 5
Midtown Ocean City
Price was $1,476, price is now $959 per person
$959
per person
Sep 18 - Sep 21
found 16 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
6.8/10 (1,024 reviews)
The staff is nice and sweet motel was affordable and nice

Reviewed on Jul 29, 2026

Oceanic Motel

Oceanic Motel

2 out of 5
Downtown Ocean City
Price was $1,508, price is now $982 per person
$982
per person
Sep 18 - Sep 21
found 16 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
7/10 Good! (794 reviews)
I was very happy with my stay. The hotels Bayside view was beautiful. The place aas clean and very homie. It was also walking distance to the beach, boardwalk, restaurants, and bars. Ill never stay anywhere else.

Reviewed on Jul 29, 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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Princess Anne Hotel Deals

Econo Lodge Princess Anne

Econo Lodge Princess Anne

2 out of 5
10936 Market Lane US 13 Princess Anne MD
Fully refundable
$76 nightly
The price is $85 total per night from Aug 20 to Aug 21
$85 total
Aug 20 - Aug 21
Total with taxes and fees
6.6/10 (698 reviews)
"The staff were very polite. We were happy to know we had breakfast but when we went to get it, it was just cereal and toast. The milk was sitting out so we didn’t eat. The rooms were clean."

Reviewed on Jul 22, 2026

Econo Lodge Princess Anne
Americas Best Value Inn Princess Anne

Americas Best Value Inn Princess Anne

2 out of 5
30359 Mt. Vernon Road Princess Anne MD
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $82 total per night from Aug 3 to Aug 4
$82 total
Aug 3 - Aug 4
Total with taxes and fees
6.8/10 (66 reviews)
"Shetson wrong"

Reviewed on Jul 28, 2026

Americas Best Value Inn Princess Anne
Chincoteague Inn

Chincoteague Inn

2 out of 5
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $134 total per night from Aug 30 to Aug 31
$134 total
Aug 30 - Aug 31
Total with taxes and fees
Chincoteague Inn
See all 835 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 $936 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.