Princess Anne Vacations from $241

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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.
The Inn at Lewes

The Inn at Lewes

3 out of 5
Price was $269, price is now $241 per person
$241
per person
Mar 12 - Mar 14
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
6.2/10 (96 reviews)
The staff was very helpful.The gentleman even helped me get into My room and I really appreciate that

Reviewed on Jun 26, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $314, price is now $265 per person
$265
per person
Mar 12 - Mar 14
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (3,316 reviews)
They made sure our winter trip to OC was great!

Reviewed on Jan 22, 2026

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $281, price is now $248 per person
$248
per person
Mar 12 - Mar 14
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.6/10 Excellent! (1,118 reviews)
it was beautiful good experiance

Reviewed on Jan 21, 2026

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
Price was $306, price is now $273 per person
$273
per person
Mar 12 - Mar 14
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8/10 Very Good! (75 reviews)
Felt less up to date than pictured

Reviewed on Nov 20, 2025

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

2.5 out of 5
Midtown Ocean City
Price was $327, price is now $292 per person
$292
per person
Mar 12 - Mar 14
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.8/10 Excellent! (1,000 reviews)
Clean. Comfortable, walking distance to convention center, food and shopping

Reviewed on Jan 19, 2026

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Princess Anne Hotel Deals

Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street Chincoteague VA
$111 nightly
The price is $125 total per night from Jan 26 to Jan 27
$125 total
Jan 26 - Jan 27
Total with taxes and fees
9.8/10 Exceptional! (501 reviews)
Perfect! Adorable, clean, well and nicely appointed — with a view and an affordable price. I’ll be back!

Reviewed on Jan 13, 2026

Key West Cottages
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! (1,002 reviews)
Very good

Reviewed on Jan 16, 2026

Hampton Inn & Suites Salisbury/Fruitland
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
$80 nightly
The price is $90 total per night from Feb 1 to Feb 2
$90 total
Feb 1 - Feb 2
Total with taxes and fees
6.4/10 (895 reviews)
Great stay. Ashley at the front desk was excellent. Extremely kind and helpful. I will be returning and recommending to stay here because of her!

Reviewed on Jan 19, 2026

Best Western Salisbury Plaza
See all 777 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 $241 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.