Highland County Vacations & Trips from $457
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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.
Massanuttens Shenandoah Villas by Tripforth
Price was $619, price is now $457 per person
$457
per person
Mar 19 - Mar 23
just found
Roundtrip non-stop flight included
Orlando (MCO) to Weyers Cave (SHD)
7.6/10 Good! (144 reviews)
Condo was clean. Jacuzzi tub needs updating. Everything else was good.
Reviewed on Dec 31, 2025
Cave Hill Farm Bed & Breakfast
Price was $532, price is now $494 per person
$494
per person
Mar 19 - Mar 23
just found
Roundtrip non-stop flight included
Orlando (MCO) to Weyers Cave (SHD)
9.4/10 Exceptional! (335 reviews)
Beautifully decorated and furnished. Bridal room canopy bed is gorgeous, and we loved the Jacuzzi tub and fireplace. Great old photos and historical information. Inn is located on a quiet pretty farm road.
Reviewed on Jan 4, 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
Simple. Rustic. Luxury.
Monterey VA
9.8/10 Exceptional! (174 reviews)
We had a wonderful time at this location and would recommend it to anyone looking for a secluded get away. You will not have cellphone service, but the wifi connection is strong.The hot tub was very clean with a great view. We enjoyed watching the sun set over the mountains and star gazing.The wood ...
Reviewed on Jan 7, 2026
The Omni Homestead Resort & Spa
7696 Sam Snead Highway Hot Springs VA
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $336 total per night from Feb 16 to Feb 17
$336 total
Feb 16 - Feb 17
Total with taxes and fees
8.6/10 Excellent! (995 reviews)
The staff was excellent in every regard. Food was subpar.
Reviewed on Jan 2, 2026
Marlinton Motor Inn
21507 Seneca Trl Marlinton WV
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $90 total per night from Feb 8 to Feb 9
$90 total
Feb 8 - Feb 9
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Clean room, friendly front desk staff
Reviewed on Feb 2, 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.
