Deals on vacations and trips to Highland County

Save when you book Highland County, VA package deals

Choose two or more items and save on your trip:

Highland County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
Price was $488, price is now $446 per person
$446
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Weyers Cave (SHD)
Free self parking is available and the hotel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Luggage storage and a safe deposit box are also provided.
The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

3.5 out of 5
Price was $573, price is now $482 per person
$482
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Weyers Cave (SHD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a terrace, and a garden are also on offer.
Hotel 24 South

Hotel 24 South

3 out of 5
Price was $556, price is now $502 per person
$502
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Weyers Cave (SHD)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, a 24-hour business center, and a lobby fireplace are also offered.
Holiday Inn Express & Suites Waynesboro East by IHG

Holiday Inn Express & Suites Waynesboro East by IHG

2.5 out of 5
Price was $929, price is now $868 per person
$868
per person
Oct 23 - Oct 25
found 17 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Weyers Cave (SHD)
This hotel features an indoor pool and a gym. Enjoy the free buffet breakfast each morning. Self parking is offered and the front desk is staffed around-the-clock.
Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
Price was $843, price is now $802 per person
$802
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Top Highland County hotels deals

Deck, Views, Games: 10BR Home in Shenandoah Valley

Deck, Views, Games: 10BR Home in Shenandoah Valley

McDowell VA
Get rates
This vacation home features barbecue grills.
Pool
Kitchen
Cabin on Mountain Stream, Surrounded by Forest

Cabin on Mountain Stream, Surrounded by Forest

McDowell VA
Get rates
This cabin featured laundry facilities and barbecue grills.
Kitchen
Washer
Secluded 3 bedroom home with creek in the back yard

Secluded 3 bedroom home with creek in the back yard

Monterey VA
Get rates
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
Solitude on 172 private acres in Highland County.

Solitude on 172 private acres in Highland County.

Doe Hill VA
Get rates
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
The Omni Homestead Resort & Spa

The Omni Homestead Resort & Spa

4 out of 5
7696 Sam Snead Highway Hot Springs VA
Free Cancellation
Reserve now, pay when you stay
$294 nightly
The price is $336 total per night
$336 total
Sep 21 - Sep 22
Total with taxes and fees
This historic resort features a golf course, a full-service spa, and 9 restaurants. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. Bring the family and enjoy the lazy river, children's club, and kid-friendly dining.
Pool
Hot Tub
Corduroy Inn and Lodge, Trademark Collection by Wyndham

Corduroy Inn and Lodge, Trademark Collection by Wyndham

2.5 out of 5
5811 Snowshoe Drive Snowshoe WV
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $112 total per night
$112 total
Sep 15 - Sep 16
Total with taxes and fees
Ski-in/ski-out access, 2 restaurants, and a gym are all featured at this smoke-free hotel. There's a free ski shuttle, and ski rentals, ski passes and ski storage are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.
Pet friendly
Parking included
Don't see what you're looking for?
See all available properties in Highland County
View all properties
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 Highland County attractions

Maple Museum

You can spend an afternoon browsing the exhibits at Maple Museum during your trip to Monterey. Amble around the area's parks or experience its museums.
See properties

Photos of local treasures

Browse Highland County vacation photos for more inspiration

A mountainous landscape with rocky outcrops and dense forests.
A rural road with a double yellow line, surrounded by trees and hills under a partly cloudy sky.
A man carving wood at an outdoor market.

Frequently asked questions

How much are vacation packages to Highland County?
Get ready to be surprised — you could find yourself in Highland County for as little as $446. At Travelocity, we save you money and hassle with our awesome vacation packages. With hotels, flights and tours all in one place, what's stopping you?
Where can I get the best vacation package deals for Highland County?
It's simple — head to Travelocity. With as many as 400 partner airlines and 1,000,000 worldwide properties, it's a breeze to craft a Highland County package deal that satisfies your wanderlust.
Why should I book my Highland County vacation package with Travelocity?
Because we believe in crafting one-of-a-kind vacation experiences. From flights and hotels to car rentals and activities, our packages make it a breeze to save. Our customer care is on hand 24/7 to ensure you're never alone. We also offer a Price Match Guarantee, so you can book your vacation knowing you've landed the best deal around.
Will I save money on my Highland County car rental if I combine it with hotels and flights?
Bundling your bookings into a Highland County vacation package will certainly save you money. Choose a car and flight; a hotel, car and flight; or a hotel and car. There's no better way to explore the greater Highland County area than with your own rental car. You can also add experiences and activities to your Travelocity package.
Which airport is best for Highland County?
Book a flight to Shenandoah Valley Regional Airport (SHD) or Greenbrier Valley Airport (LWB). They are the major airports for passengers heading in and out of Highland County.
What is there to do in Highland County?
Highland County boasts hidden gems around every turn, however ensure you plan a visit to both Maple Museum and Sugar Tree Country Store while you're here. These two attractions are a must-see for visitors to the region.

Explore More Ways to Travel with Travelocity