Princess Anne Vacations from $590

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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.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Save 100% on your flight
Price was $771, price is now $590 per person
$590
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.8/10 Excellent! (1,000 reviews)
Stay here frequently. Great location, friendly staff.

Reviewed on Jun 30, 2026

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Price was $1,327, price is now $898 per person
$898
per person
Sep 17 - Sep 20
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Salisbury (SBY)
6.8/10 (8 reviews)
the room was ok... shown signs of not maintaining ......weather stripping on the front door was warn and broken... panel under front window was coming off the wall in the bathroom it looks like they tried to fix a broken molding with puddy bathroom had what looked like mold or buildup of heavy soap scum in the shower. no wifi, tv didnt work even with cable box attached and light showing green it did show lighted as on option to pick in the menu. the lamp between the beds didnt turn on ... i did bring the issue of the wifi no working to the attention of the front desk and was told to keep trying it. he was a nice guy and very friendly at check in, but it was almost like he didnt want to look into it .

Reviewed on Jun 22, 2026

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Price was $2,337, price is now $1,702 per person
$1,702
per person
Sep 24 - Sep 27
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Salisbury (SBY)
8.2/10 Very Good! (35 reviews)
The rooms were not clean, and very old. Floors were covered in sand , and there were holes in the walls, and door handles coming off. The worst part was NO HOT WATER. We could not take a shower for 2 days , and when telling the front desk, they gave us attitude. Terrible customer service

Reviewed on Jun 27, 2026

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $2,957, price is now $2,336 per person
$2,336
per person
Sep 24 - Sep 27
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Salisbury (SBY)
8.2/10 Very Good! (733 reviews)
No parking in garage so staff took car an parked it im handicap so couldn't walk to far thank you

Reviewed on Jun 30, 2026

Hyatt Place Dewey Beach

Hyatt Place Dewey Beach

3 out of 5
Save 100% on your flight
Price was $1,180, price is now $959 per person
$959
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.8/10 Excellent! (1,002 reviews)
The hotel was good. The location was great!

Reviewed on Jun 27, 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.
See properties

Princess Anne Hotel Deals

Econo Lodge Princess Anne

Econo Lodge Princess Anne

2 out of 5
10936 Market Lane US 13 Princess Anne MD
$81 nightly
The price is $90 total per night from Jul 8 to Jul 9
$90 total
Jul 8 - Jul 9
Total with taxes and fees
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
$75 nightly
The price is $83 total per night from Jul 2 to Jul 3
$83 total
Jul 2 - Jul 3
Total with taxes and fees
Americas Best Value Inn Princess Anne
Best Western Salisbury Plaza

Best Western Salisbury Plaza

2.5 out of 5
1735 N Salisbury Blvd Salisbury MD
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $125 total per night from Jul 12 to Jul 13
$125 total
Jul 12 - Jul 13
Total with taxes and fees
6.4/10 (956 reviews)
"Check in was slow. Agent tried to be pleasant. Property and room were old and worn down. Breakfast was ok. Starting at 9 am, two hours before checkout room service began knocking at the door asking us if we were leaving. I don’t think they understood English. I was happy to leave."

Reviewed on Jun 29, 2026

Best Western Salisbury Plaza
See all 832 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 $590 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.