Princess Anne Vacations from $525

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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.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $644, price is now $525 per person
$525
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Salisbury (SBY)
9/10 Wonderful! (3,316 reviews)
Excellent deal and surprisingly inexpensive. Room was big, clean and comfortable.

Reviewed on Jan 28, 2026

Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Downtown Bethany Beach
Save 100% on your flight
Price was $794, price is now $606 per person
$606
per person
Apr 3 - Apr 6
found 11 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (770 reviews)
Super helpful staff, breakfast was amazing

Reviewed on Jan 28, 2026

Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
North Ocean City
Price was $741, price is now $568 per person
$568
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Salisbury (SBY)
8.2/10 Very Good! (1,825 reviews)
Clean, comfortable and quiet.

Reviewed on Dec 28, 2025

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $2,191, price is now $1,733 per person
$1,733
per person
Apr 3 - Apr 9
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!

Reviewed on Aug 23, 2025

Monte Carlo Condos

Monte Carlo Condos

3 out of 5
Downtown Ocean City
Price was $929, price is now $758 per person
$758
per person
Apr 3 - Apr 9
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Salisbury (SBY)
6.8/10 (58 reviews)
Block away from the boardwalk. Friendly staff. Plenty of room in the condo.

Reviewed on Sep 29, 2025

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Princess Anne Hotel Deals

Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street Chincoteague VA
$119 nightly
The price is $134 total per night from Feb 1 to Feb 2
$134 total
Feb 1 - Feb 2
Total with taxes and fees
9.8/10 Exceptional! (505 reviews)
Love the resort!

Reviewed on Jan 21, 2026

Key West Cottages
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
$84 nightly
The price is $94 total per night from Feb 4 to Feb 5
$94 total
Feb 4 - Feb 5
Total with taxes and fees
6.4/10 (897 reviews)
It was a wonderful stay the evening and over nigjt staff was brilliant

Reviewed on Jan 23, 2026

Best Western Salisbury Plaza
Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland

2.5 out of 5
304 Prosperity Lane Fruitland MD
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Feb 8 to Feb 9
$109 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
Generally, a good place to stay.

Reviewed on Jan 22, 2026

Hampton Inn & Suites Salisbury/Fruitland
See all 774 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 $525 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.