Princess Anne Vacation Packages

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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.

Top Princess Anne Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
North Ocean City
per person
Oct 8 - Oct 12
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
8.2/10 Very Good! (1,410 reviews)
The wait for the elevator could get backed up… and layout in the lobby could be better, very congested especially during check in

Reviewed on Aug. 5, 2025

The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
per person
Oct 24 - Oct 27
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
9.8/10 Exceptional! (263 reviews)
I am so glad I chose Surf Shanty to stay at! The man at the front desk was so nice and helpful upon checking in. The location was perfect! Less than a block to the beach, on the quieter end of the strip but still walkable to everything. The room was clean and you can tell they put thought into this hotel. All the colors and decor are cohesive and beachy. There is an outdoor shower to rinse the sand off before going back to your room. The beds are super comfortable. We will definitely be back!

Reviewed on Aug. 5, 2025

Comfort Inn & Suites Milford

Comfort Inn & Suites Milford

2.5 out of 5
per person
Oct 24 - Oct 27
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
8/10 Very Good! (575 reviews)
If details matter, you won’t like this hotel. My sink faucet was leaking. My tub faucet was dripping. Tub base was stained. Otherwise my stay was fine. Nice people at the desk.

Reviewed on Jul. 9, 2025

Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
per person
Oct 24 - Oct 27
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
8.6/10 Excellent! (1,000 reviews)
Noisy at night but expected. No food but a vendimg machine was available Nice and clesn room .

Reviewed on Aug. 5, 2025

The Marylander Condo & Hotel

The Marylander Condo & Hotel

4 out of 5
North Ocean City
per person
Oct 8 - Oct 12
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
8/10 Very Good! (38 reviews)
As great location and close to the beach access.

Reviewed on Aug. 12, 2024

Ready to book your vacation to Princess Anne?

 

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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
The price is CA $112 per night from Aug 12 to Aug 13
CA $112
CA $124 total
Aug 12 - Aug 13
includes taxes & fees
6.6/10 (629 reviews)
Wonderful stay! Will definitely stay again!
"Very nice place to crash and hangout while I wait for my bus to arrive. Econo Lodge has always been a favorite of mine."

Reviewed on Aug. 3, 2025

Econo Lodge 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
The price is CA $110 per night from Sep 2 to Sep 3
CA $110
CA $123 total
Sep 2 - Sep 3
includes taxes & fees
6.2/10 (816 reviews)
"Loved It All"

Reviewed on Aug. 1, 2025

Best Western Salisbury Plaza
Atlantic Shores Inn and Suites

Atlantic Shores Inn and Suites

2 out of 5
6273 Maddox Blvd, Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Sep 1 to Sep 2
CA $110
CA $124 total
Sep 1 - Sep 2
includes taxes & fees
7.2/10 Good! (1,009 reviews)
"Owner was top notch!! Location close to everything!!"

Reviewed on Aug. 2, 2025

Atlantic Shores Inn and Suites
See all 805 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a Princess Anne vacation package cost?
You'll find cheap prices from CA $715 on Expedia for your Princess Anne escape. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Princess Anne costs.
What are the cheapest months to go to Princess Anne?
December, January and February are great times to look for cheap Princess Anne vacation packages. Opting to travel in less busy months means you can generally find lower prices on flights and hotels.
How many days is enough for Princess Anne?
Generally, a handful of days is enough to visit the major attractions during your Princess Anne vacation. However, if you prefer to have time to rest or take day tours, consider extending your itinerary.
How to find the best Princess Anne package deals?
Landing a cheap Princess Anne package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Princess Anne package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Princess Anne vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still get the freedom to create a personalized Princess Anne vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Princess Anne?
If you're planning an impromptu Princess Anne trip, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Princess Anne?

  1. Choose your travel dates: The things you plan to do in Princess Anne and your favourite season will help you decide when to get away.
  2. Budget wisely: Besides the price of your hotel, you should consider other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that may come up during your trip to Princess Anne.
  3. Work out your trip length: Consider how long you'd like to spend exploring Princess Anne. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your accommodations and airfare: Once you've settled on your travel dates and duration, book the ideal Princess Anne vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.