
Eastern Panhandle Vacations from $581
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Your Eastern Panhandle Vacation
Leave the planning to us with an Eastern Panhandle vacation package. With everything arranged before you depart, the only thing you'll need to do is sit back, chill out and experience this destination's wonders to the fullest. With so much to explore on a trip to Eastern Panhandle, it can be difficult to know where to start. Kick off your journey in Winchester at Shenandoah Valley Discovery Museum and Dinosaur Land — two leading attractions here. Another city worthy of a spot on your itinerary is Martinsburg. Don't miss Martinsburg Mall and Chesapeake and Ohio Canal. Expedia is a one-stop shop for organizing your Eastern Panhandle vacation. From hotels and flights, to activities and more, we're here to help you curate a travel experience like no other.
The Latest Eastern Panhandle vacation packages

Phoenix Park Hotel
Reviewed on Aug 23, 2026



Hotel Burg
Reviewed on Aug 22, 2026

Where to stay in Eastern Panhandle

Timberline
If you're spending some time in Timberline, Timberline Four Season Resort and Canaan Valley are top sights worth seeing.

The Woods
If you're spending some time in The Woods, Sleepy Creek Wildlife Management Area and The Woods Resort Mountain View Course are top sights worth seeing.

Old Timberline
While Old Timberline might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Timberline Four Season Resort and Canaan Valley.

Old Town Winchester
Old Town Winchester is known for its ample dining options, and you can make a stop by Shenandoah Valley Discovery Museum and Bright Box Theater while in the area.

Northface
If you're looking for some top things to see and do in Northface and surrounding area, you can visit Timberline Four Season Resort and Canaan Valley.
Stay near popular Eastern Panhandle attractions

Harpers Ferry National Historical Park
Canaan Valley Ski Resort
Summit Point Motorsports Park

Canaan Valley

Blackwater Falls
Potomac Eagle Scenic Railroad
Shenandoah University
Eastern Panhandle Hotel Deals

Quality Inn Harpers Ferry - Charles Town
"Everything was great. Wish there was a hotel rule no smoking near the entrance. It filters into the lobby."
Reviewed on Aug 22, 2026

Keyser Inn
"This was such a refreshing change from the chain motels. The room was clean and quaint, the front desk lady was funny, helpful and a joy to talk with. I thoroughly enjoyed my stay here and would do so again in the future if the opportunity presented itself."
Reviewed on Aug 22, 2026

Holiday Inn Express Charles Town by IHG
"For the price and location of the hotel, it was very nice. The only issue we had was that we had allowed messy neighbor. As we were checking out, we notified the staff and they immediately got on it."
Reviewed on Aug 19, 2026
Find the Best Eastern Panhandle Vacation Packages
Eastern Panhandle Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |



















