Highland County Vacations & Trips from $878
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Your Highland County Vacation
Leave all the planning to us with a Highland County vacation package. With everything organized before you leave home, the only thing you'll need to do is relax and experience this destination's many wonders. Get your trip to Highland County off to an unforgettable start by making Monterey your first stop. This is a popular city with visitors from all over. From the instant you book your Highland County vacation to the second you come back home, Expedia has your back every step of the way.
Top destinations in Highland County
Monterey
The Latest Highland County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Waynesboro
Price was $975, price is now $878 per person
$878
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tallahassee (TLH) to Weyers Cave (SHD)
7.6/10 Good! (1,000 reviews)
The room was spotless. Everything worked. A bit dated, but very roomy and comfortable.
And Waffle House is around the corner.
Only minus - Confusing to access parking lot. NOTE: Cannot be accessed from the main road. You can see it, but you can't get in.
Reviewed on Jul 4, 2026
Best Western Plus Waynesboro Inn & Suites Conference Center
Price was $1,218, price is now $1,058 per person
$1,058
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tallahassee (TLH) to Weyers Cave (SHD)
8.6/10 Excellent! (1,001 reviews)
Was great till I left my hat in my room when we checked out and called later to tell them about my hat and they never called me back about it
Reviewed on Jul 6, 2026
The Blackburn Inn and Conference Center
Price was $1,208, price is now $1,071 per person
$1,071
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tallahassee (TLH) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,005 reviews)
The A/C in our room was broken…80° all night. Clearly there were A/C issues in the entire floor as the lobby on the 4th floor was hot too. Called the front desk; never offered another room.
The property is very cool and historic. It was disappointing to have this issue. The rooms were beautifully decorated and well apportioned.
The on site restaurant is only open for breakfast which was also frustrating.
Reviewed on Jul 8, 2026
Holiday Inn Express & Suites Waynesboro East by IHG
Price was $1,148, price is now $1,024 per person
$1,024
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tallahassee (TLH) to Weyers Cave (SHD)
9/10 Wonderful! (582 reviews)
Friendly staff, very clean and updated. Good breakfast options.
Reviewed on Jul 7, 2026
Massanutten Resort
Price was $1,086, price is now $977 per person
$977
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tallahassee (TLH) to Weyers Cave (SHD)
8/10 Very Good! (1,395 reviews)
Nice rooms great staff only thing things should be open longer it is summer
Reviewed on Jul 9, 2026
Find the Best Highland County Vacation Packages
Highland County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Ronald Reagan Washington National Airport (DCA) |
Highland County Hotel Deals
Games Galore! Riverfront Group Retreat in McDowell
McDowell VA
10/10 Exceptional! (7 reviews)
"We had a larger group and the host was extremely helpful and responsive for all our needs. The house was in perfect condition in the perfect private location"
Reviewed on Apr 7, 2026
Cabin on Mountain Stream, Surrounded by Forest
McDowell VA
9.8/10 Exceptional! (150 reviews)
"Out of all the places we have stayed at. This is the best one. Cabin is well stocked. Furniture is very comfortable.My favorite part was sitting on the deck looking & lessoning to the stream. It’s very PEACEFUL here. My husbands favorite part was fishing the surrounding rivers/streams."
Reviewed on Jun 6, 2026
Solitude on 172 private acres in Highland County.
Doe Hill VA
10/10 Exceptional! (23 reviews)
"Perfect place to get away from it all! We made many memories and our dogs loved being included in our vacation. Host was very responsive and super friendly!"
Reviewed on Jul 4, 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.
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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.
