Princess Anne Vacations

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.

Princess Anne Hotel Deals

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 1 to Feb 2
$109 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
Room was fine..I was not cleaned the second day we were there. The breakfast is just ok..it could use a bit more variety to also accommodate vegans/vegetarians

Reviewed on Jan 5, 2026

Hampton Inn & Suites Salisbury/Fruitland
Courtyard by Marriott Salisbury

Courtyard by Marriott Salisbury

3 out of 5
128 Troopers Way Salisbury MD
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $120 total per night from Jan 22 to Jan 23
$120 total
Jan 22 - Jan 23
Total with taxes and fees
8.4/10 Very Good! (968 reviews)
The staff were wonderful, accommodating, and understanding. The room was amazing and spacious, housekeepers were friendly, and the little make shift animal was the most adorable thing ever. The bed and pillows are super soft, like floating on clouds. This was the best homecation ever and will be ...

Reviewed on Dec 29, 2025

Courtyard by Marriott Salisbury
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 18 to Jan 19
$125 total
Jan 18 - Jan 19
Total with taxes and fees
9.8/10 Exceptional! (498 reviews)
Check in was a breeze the front desk agent was very friendly and resourceful! The cottage was amazing and clean ! Would definitely recommend

Reviewed on Jan 5, 2026

Key West Cottages
See all 782 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 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.