Princess Anne Vacations from $693

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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 $883, price is now $693 per person
$693
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Salisbury (SBY)
6.2/10 (97 reviews)
This was the best place I stayed. However, it was not at the Inn for which I paid. When I arrived, no one was in the office, but I ran into some guys renovating the property. The called the boss for me, and he put me at a much nicer property at Staybridge Suites, 34521 Old Postal Lane, Lewes. That was the nicest place Instayed on this vacations so far and the breakfast was the best. The WiFi was flawless.

Reviewed on May 17, 2026

Hotel Bethany Beach

Hotel Bethany Beach

2.5 out of 5
Save 100% on your flight
Price was $1,078, price is now $819 per person
$819
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Salisbury (SBY)
9.2/10 Wonderful! (1,413 reviews)
Everything about our 3 night stay in June was great! Check in and check out were easy, the property was clean, staff was friendly, breakfast was delicious and had a nice assortment of items. The rooms were updated and comfortable. Would definitely stay again!

Reviewed on Jun 9, 2026

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $1,840, price is now $1,422 per person
$1,422
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
7.4/10 Good! (171 reviews)
Got better than what I expected for the price. Front desk ladies were happy & helpfully. Only thing that would be nice would be some type of dimmer lights for night, outlets near beds & softer beds. Will definately be staying here again! Full kitchen with full size fridge saved us $ not having to eat out. It's like a hotel sized condo.

Reviewed on Oct 1, 2025

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 $2,611, price is now $2,032 per person
$2,032
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Salisbury (SBY)
9/10 Wonderful! (832 reviews)
The room had more sand than the beach. The refrigerator and countertops hadn't been cleaned on years

Reviewed on Jun 7, 2026

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was $1,699, price is now $1,377 per person
$1,377
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
8.4/10 Very Good! (40 reviews)
Beautiful place that aided to my family having a great vacation! 10/10 and I’d definitely stay there again!

Reviewed on May 31, 2026

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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 refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Jun 17 to Jun 18
$90 total
Jun 17 - Jun 18
Total with taxes and fees
6.6/10 (687 reviews)
"pool was green, no staff present when key card quit working"

Reviewed on Jun 2, 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
$75 nightly
The price is $83 total per night from Jun 11 to Jun 12
$83 total
Jun 11 - Jun 12
Total with taxes and fees
6.8/10 (60 reviews)
"It was clean but dated!"

Reviewed on May 22, 2026

Americas Best Value Inn Princess Anne
Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street Chincoteague VA
$300 nightly
The price is $337 total per night from Jun 28 to Jun 29
$337 total
Jun 28 - Jun 29
Total with taxes and fees
9.8/10 Exceptional! (575 reviews)
"The property was gorgeous- cottage was perfect. We booked one of the 1 bedroom cottages. It had a small cooktop, microwave, fridge, freezer, dishwasher and kitchen supplies. Comfortable living room area. Bedroom and bathroom were both comfortable and beautifully decorated. Lovely front porch to watch ..."

Reviewed on Jun 7, 2026

Key West Cottages
See all 826 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 $693 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.