Deals on vacations and trips to Highland County

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Highland County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Massanutten Resort

Massanutten Resort

2.5 out of 5
Price was $440, price is now $388 per person
$388
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Weyers Cave (SHD)
This hotel features a golf course, a full-service spa, and 4 restaurants. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy snowboarding. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities.
The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

3.5 out of 5
Price was $616, price is now $487 per person
$487
per person
Oct 22 - Oct 25
found 11 hours ago
Roundtrip flight included
Hartford (BDL) 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.
Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
Price was $960, price is now $812 per person
$812
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
Hotel Madison & Shenandoah Conference Ctr

Hotel Madison & Shenandoah Conference Ctr

3.5 out of 5
Price was $629, price is now $553 per person
$553
per person
Oct 22 - Oct 25
found 11 hours ago
Roundtrip flight included
Hartford (BDL) to Weyers Cave (SHD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.
Massanuttens Shenandoah Villas by Tripforth

Massanuttens Shenandoah Villas by Tripforth

4 out of 5
Price was $1,170, price is now $1,037 per person
$1,037
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Weyers Cave (SHD)
This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. There's a picnic area and multilingual staff can provide around-the-clock assistance.

Top Highland County hotels deals

Games Galore! Riverfront Group Retreat in McDowell

Games Galore! Riverfront Group Retreat in McDowell

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

Cabin on Mountain Stream, Surrounded by Forest

McDowell VA
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This cabin featured laundry facilities and barbecue grills.
Solitude on 172 private acres in Highland County.

Solitude on 172 private acres in Highland County.

Doe Hill VA
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This vacation home featured laundry facilities and barbecue grills.
Secluded 3 bedroom home with creek in the back yard

Secluded 3 bedroom home with creek in the back yard

Monterey VA
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A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
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
$242 nightly
The price is $277 total per night
$277 total
Sep 7 - Sep 8
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. There's fun for all ages with a lazy river and a children's club, and families will appreciate the onsite laundry facilities.
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
$89 nightly
The price is $102 total per night
$102 total
Aug 30 - Aug 31
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.
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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.
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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 $388. 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.

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