Cheap Flights to Highland County from $355 (2026/2027)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How Much Does it Cost To Fly To Highland County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Oct 6 - Tue, Oct 13
DTW
Detroit Metropolitan Wayne County
SHD
Shenandoah Valley Regional
$466 Roundtrip, found 1 day ago
$466
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Detroit Metropolitan Wayne County to Shenandoah Valley Regional, returning Tue, Oct 13, priced at $466 found 1 day ago
Tue, Oct 6 - Tue, Oct 13
DTW
Detroit Metropolitan Wayne County
SHD
Shenandoah Valley Regional
$486 Roundtrip, found 1 day ago
$486
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Detroit Metropolitan Wayne County to Shenandoah Valley Regional, returning Tue, Oct 13, priced at $486 found 1 day ago
Tue, Oct 6 - Tue, Oct 13
DTW
Detroit Metropolitan Wayne County
SHD
Shenandoah Valley Regional
$505 Roundtrip, found 1 day ago
$505
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Detroit Metropolitan Wayne County to Shenandoah Valley Regional, returning Tue, Oct 13, priced at $505 found 1 day ago
Tue, Oct 6 - Tue, Oct 13
DTW
Detroit Metropolitan Wayne County
SHD
Shenandoah Valley Regional
$524 Roundtrip, found 1 day ago
$524
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Detroit Metropolitan Wayne County to Shenandoah Valley Regional, returning Tue, Oct 13, priced at $524 found 1 day ago
Sat, Sep 5 - Tue, Sep 8
IND
Indianapolis Intl.
SHD
Shenandoah Valley Regional
$540 Roundtrip, found 1 day ago
$540
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Sep 5 from Indianapolis Intl. to Shenandoah Valley Regional, returning Tue, Sep 8, priced at $540 found 1 day ago
Tue, Oct 6 - Tue, Oct 13
DTW
Detroit Metropolitan Wayne County
SHD
Shenandoah Valley Regional
$576 Roundtrip, found 1 day ago
$576
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Detroit Metropolitan Wayne County to Shenandoah Valley Regional, returning Tue, Oct 13, priced at $576 found 1 day ago
Tue, Oct 6 - Tue, Oct 13
DTW
Detroit Metropolitan Wayne County
SHD
Shenandoah Valley Regional
$582 Roundtrip, found 1 day ago
$582
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Detroit Metropolitan Wayne County to Shenandoah Valley Regional, returning Tue, Oct 13, priced at $582 found 1 day ago
Tue, Oct 6 - Tue, Oct 13
DTW
Detroit Metropolitan Wayne County
SHD
Shenandoah Valley Regional
$587 Roundtrip, found 1 day ago
$587
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Detroit Metropolitan Wayne County to Shenandoah Valley Regional, returning Tue, Oct 13, priced at $587 found 1 day ago
OriginDestinationTravel DatesFlights From*
ORDMount SidneyOctober 29 to November 2$234
DENMount SidneyNovember 2 to November 7$435
TPAMount SidneyOctober 27 to October 31$488
BOSMount SidneyOctober 2 to October 4$572
IAHMount SidneyOctober 8 to October 11$599
EWRMount SidneyNovember 4 to November 6$698
*Prices include taxes and fees

Best Highland County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Staunton Conference Center by IHG
3.0-star property

Holiday Inn Staunton Conference Center by IHG

Aug 23 - Aug 30

7 night stay

Hartford (BDL) to Weyers Cave (SHD)

United • Non-stop roundtrip • Coach
Price was $899, price is now $699 per person
$699
per person
found 1 day ago
Massanuttens Shenandoah Villas by Tripforth
4.0-star property

Massanuttens Shenandoah Villas by Tripforth

Aug 23 - Aug 30

7 night stay

Hartford (BDL) to Weyers Cave (SHD)

United • Non-stop roundtrip • Coach
Price was $1,174, price is now $925 per person
$925
per person
found 1 day ago
The Summit at Massanutten Resort by Tripforth
3.5-star property

The Summit at Massanutten Resort by Tripforth

Aug 23 - Aug 30

7 night stay

Hartford (BDL) to Weyers Cave (SHD)

United • Non-stop roundtrip • Coach
Price was $1,143, price is now $936 per person
$936
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Hartford to Highland County
View all trips

Travelers ❤️ These Highland County 🏨

Games Galore! Riverfront Group Retreat in McDowell

Games Galore! Riverfront Group Retreat in McDowell

McDowell VA
Book a stay at this family-friendly vacation home in McDowell. Enjoy private pools, patios, and an in-room coffeemaker. Popular attraction Sugar Tree Country Store is located nearby.
Opens in a new windowGames Galore! Riverfront Group Retreat in McDowell
Cabin on Mountain Stream, Surrounded by Forest

Cabin on Mountain Stream, Surrounded by Forest

McDowell VA
Book a stay at this family-friendly cabin in McDowell. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attraction Sugar Tree Country Store is located nearby.
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

Opens in a new windowCabin on Mountain Stream, Surrounded by Forest
Solitude on 172 private acres in Highland County.

Solitude on 172 private acres in Highland County.

Doe Hill VA
Stay at this vacation home in Doe Hill. Enjoy laundry facilities, balconies or patios, and cable/satellite TV service. Our guests praise the helpful staff in our reviews. Popular attractions Sugar Tree Country Store and Bullpasture Mountain are located nearby.
10/10 Exceptional! (29 reviews)
"This is a remote setting, surrounded by mountains and wildlife. It is quiet, peaceful and a reminder that there are still places like this in the world. All the modern conveniences are there including Wifi and Dish network. No cellular service (but who cares?). If you are fortunate to have clear ..."

Reviewed on Aug 20, 2026

Opens in a new windowSolitude on 172 private acres in Highland County.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Secluded 3 bedroom home with creek in the back yard

Secluded 3 bedroom home with creek in the back yard

Monterey VA
Stay at this vacation home in Monterey. Enjoy free WiFi, a garden, and laundry facilities. Popular attraction Maple Museum is located nearby.
Opens in a new windowSecluded 3 bedroom home with creek in the back yard
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.

Frequently asked questions

How much is the cheapest flight to Highland County?
Based on prices found over the last seven days, a roundtrip flight to Highland County was as low as $234. If you're flexible with your dates, it's easier to snap up a great bargain. This price was available on Travelocity for flights to Highland County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Highland County?
Make sure you leave October empty in your calendar, because it's the cheapest month to fly to Highland County. That's according to Travelocity's direct flight demand from January to December last year. With more money in your wallet, you can go on a spending spree, go to a concert or whatever makes you happy.
How can I check my flight status to Highland County?
"Trips" has you covered when it comes to details related to your flight to Highland County. This handy portal lets you manage everything in the same place, from looking up your flight status to making updates to your itinerary. Click on Trips at the top right of the Travelocity homepage and then create a new account or sign in to an existing one. Alternatively, download the Travelocity app and access your information while you're out and about. Whether you have the family flying with you or you're a lone adventurer, all your travel plans are right there at your fingertips.
How do I find the best deals on flights to Highland County?
Be flexible with your dates and there's a good chance you'll find an awesome deal. When searching for flights on Travelocity, click the "Flexible dates" box at the top of the page to reveal prices for nearby days. Also try to book ahead of schedule and avoid vacation periods. In the last seven days, the best price for a roundtrip flight to Highland County was $234. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Highland County with Travelocity?
An exciting vacation is just a click away when you make a booking with Travelocity. With a wide selection of choices and competitive deals on cheap family flights, hotels, activities and rental cars, we make it simple to find the best prices to suit your needs. You can also make the most of our 24/7 social media assistance and free cancellations on most activities and hotels throughout every stage of the process. Wander wisely with us and lock in your cheap flights to Highland County today.
What are the most popular flight routes to Highland County?
Browse through these top flight routes to Highland County and start planning you next amazing adventure:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Washington Dulles Intl. Airport (IAD) - 1,859 flights a month.
  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Washington Dulles Intl. Airport (IAD) - 1,347 flights a month.
  • Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Washington Dulles Intl. Airport (IAD) - 1,321 flights a month.

How much is a flight to Highland County on average?
Get your next dream vacation off to the best start by nabbing an awesome deal with Travelocity. In the last seven days, roundtrip flights to Highland County cost between $234 and $698. Check out our site and secure a ticket that fits within your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Highland County?
The duration of a direct flight to Highland County varies, but these are the average travel times for a selection of popular routes:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Washington Dulles Intl. Airport (IAD) - 1 hour and 47 minutes
  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Washington Dulles Intl. Airport (IAD) - 1 hour and 29 minutes
  • Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Washington Dulles Intl. Airport (IAD) - 1 hour and 29 minutes

What can I expect on a flight to Highland County?
That all depends on your departure point and which airline company you're traveling with. You'll likely find all kinds of flights to Highland County, from business class trips to cheap flights for family vacations. Most airlines on long-haul flights usually offer warm meals and entertainment as well as games to keep the kids happy.