Somerset County Vacations & Trips from $1,328
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Your Somerset County Vacation
Book a vacation package to Somerset County and make planning your adventure quick and easy. With the logistics organized before you depart, you can focus on enjoying every moment in this amazing destination. Get your trip to Somerset County off to a great start by experiencing its most renowned cities. Princess Anne is one you can't miss. When it's time to stop dreaming and start doing, Expedia will help turn your Somerset County vacation into a reality.
Top destinations in Somerset County
The Latest Somerset County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Beach Walk
Downtown Ocean City
$1,622
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.6/10 Good! (113 reviews)
We would definitley stay at the Beach Walk again for a short stay, the only complaints I would have is the internet one night kept going in and out and the staff really wasnt helpful about it when my boyfriend went down the next day and the third floor balcony could use some work.
Reviewed on Aug 31, 2026
Find the Best Somerset County Vacation Packages
Somerset County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Salisbury - Ocean City Wicomico Regional Airport (SBY) |
Somerset County Hotel Deals
Econo Lodge Princess Anne
10936 Market Lane US 13 Princess Anne MD
Fully refundable
$72 nightly
$80 total
Sep 21 - Sep 22
Total with taxes and fees
Historic home on Smith Island w/ dock!
Smith Island MD
$285 nightly
$302 total
Sep 7 - Sep 8
Total with taxes and fees
9.6/10 Exceptional! (52 reviews)
"The owner, Chris, was very helpful with what we needed to bring, which was so helpful. Would definitely recommend. House was clean and well stocked."
Reviewed on Aug 2, 2026
Chincoteague Inn
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
$89 nightly
$100 total
Oct 1 - Oct 2
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
"Chincoteague Inn's staff are professional and meticulous about their hospitality. We'll kept property, clean and a well furnished comfortable room is what we experienced for our stay. Thanks!"
Reviewed on Aug 31, 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.
Stay near popular Somerset County attractions
University of Maryland Eastern Shore
8.4/10 (90 reviews)
Explore the campus of University of Maryland Eastern Shore, during your travels in Princess Anne. Wander the seaside and beaches in the area.
Smith Island
9.0/10 (21 reviews)
Commune with nature and explore the great outdoors at Smith Island during your travels in Smith Island. Discover the sunsets in this relaxing area, or seek out the fishing spots.
Somers Cove Marina
8.8/10 (5 reviews)
Explore the waterfront in Crisfield with a trip to Somers Cove Marina. Discover the sunsets and seafood restaurants in this relaxing area.
Crisfield City Dock
Explore the waterfront in Crisfield with a trip to Crisfield City Dock. While in this relaxing area, you can enjoy the seafood restaurants.
Crab Island
Commune with nature and explore the great outdoors at Crab Island during your travels in Deal Island. Discover the sunsets in this relaxing area.
Mount Vernon Park
Mount Vernon Park is just one of the places to see in Mount Vernon, so why not enjoy the other things to explore during your travels?
Jersey Island
Commune with nature and explore the great outdoors at Jersey Island during your travels in Crisfield. While in this relaxing area, you can enjoy the seafood restaurants.
Wellington Beach and Park
Explore the great outdoors at Wellington Beach and Park, a lovely green space in Crisfield. While in this relaxing area, you can enjoy the seafood restaurants.
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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.
