
Princess Anne Vacations from $1,174
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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.

Miramar Condominiums
Downtown Ocean City
Price was $1,392, price is now $1,174 per person
$1,174
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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

Simple Life Motel
Midtown Ocean City
Price was $1,598, price is now $1,261 per person
$1,261
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
6.6/10 (203 reviews)
The last at front desk even showed where my son could park his car on property my stairs cuz they only provide 1 car pass. Very friendly and efficient! For just being a weekend stay!
Reviewed on Oct 12, 2025

The Shore House
West Ocean City
Price was $2,173, price is now $1,725 per person
$1,725
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
6.8/10 (598 reviews)
Overall it was perfect for country calling. There’s a shuttle at the hotel next door that we took everyday down to the entrance for $5 cash. The beds were comfortable, clean and the shower water was hot. I almost ended up cancelling though because during the off season it is nearly impossible to reach the hotel!! I called probably 10 times and couldn’t get an answer on my booking until Expedia themselves contacted me about changing the days we were staying. While the location was great, convenient and good for the price for country calling, the lack of communication was just shocking. As someone who travels often this customer service really needs to improve or I think sales will really suffer.
Reviewed on Oct 5, 2025

Kings Arms Motel
Downtown Ocean City
Price was $1,501, price is now $1,195 per person
$1,195
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
7.6/10 Good! (220 reviews)
The staff was so helpful and made sure we had plenty of towels. They even let us check in early since we arrived in town before our checkout time. Great location, and very clean.
Reviewed on Oct 6, 2025

Beach Walk
Downtown Ocean City
Price was $2,157, price is now $1,863 per person
$1,863
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
7.6/10 Good! (95 reviews)
Everything was exactly what you would expect for a budget friendly room, only complaint was that the steps and porch going to 3rd floor was sketchy and theres a large soft spot on 3rd floor side landing
Reviewed on Oct 17, 2025
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Key West Cottages
4251 Main Street Chincoteague VA
$111 nightly
The price is $125 total per night from Jan 21 to Jan 22
$125 total
Jan 21 - Jan 22
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

Hampton Inn & Suites Salisbury/Fruitland
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! (1,002 reviews)
Very good
Reviewed on Jan 16, 2026

Best Western Salisbury Plaza
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
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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