Somerset County Vacations & Trips from $781
Book a Hotel + Flight or Car together to unlock savings
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
$2,426
per person
Dec 10 - Dec 15
found 3 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Salisbury (SBY)
7.6/10 Good! (126 reviews)
We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel.
Reviewed on Oct 13, 2026
Gillis Grier Bed & Breakfast
$1,300
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Salisbury (SBY)
10/10 Exceptional! (202 reviews)
Beautiful Victorian! Friendly accommodating couple running the place. Breakfast was amazing! Property was beautiful inside and outside.
Reviewed on Oct 12, 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
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell MD
10/10 Exceptional! (23 reviews)
"Very nice place, clean and comfortable."
Reviewed on Aug 16, 2026
Best Western Salisbury Plaza
1735 N Salisbury Blvd Salisbury MD
Fully refundableReserve now, pay when you stay
$85 nightly
$96 total
Oct 19 - Oct 20
Total with taxes and fees
Wingate by Wyndham Salisbury MD Airport North
406 Punkin Ct Salisbury MD
Fully refundableReserve now, pay when you stay
$90 nightly
$101 total
Oct 18 - Oct 19
Total with taxes and fees
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.
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?
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.
Hytche athletic Center
6.0/10 (1 review)
Catch an event at Hytche athletic Center during your trip to Princess Anne. You can enjoy the restaurants while in the area.
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.
Manokin Park
Explore the great outdoors at Manokin Park, a lovely green space in Princess Anne. You can enjoy the restaurants while in the area.
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.
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Somerset County
- Vacations and getaways similar to Somerset County
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.