Highland County Vacation Packages 2026 from $518

Highland County flight + hotel vacation packages

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

Holiday Inn Staunton Conference Center by IHG

$518

per person

May 25 - May 30

just found

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.

The Blackburn Inn and Conference Center

$538

per person

May 25 - May 30

just found

Roundtrip non-stop 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

$576

per person

May 25 - May 30

just found

Roundtrip non-stop 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.

Mountainside Villas at Massanutten by Tripforth

$1,048

per person

May 25 - May 30

just found

Roundtrip non-stop flight included

Boston (BOS) to Weyers Cave (SHD)

This vacation home features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the indoor pool and perks like free self parking and free WiFi. A gym and barbecue grills are also provided.

Country Inn & Suites by Radisson, Harrisonburg, VA

$552

per person

May 25 - May 30

just found

Roundtrip non-stop flight included

Boston (BOS) to Weyers Cave (SHD)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Top Highland County hotels deals

Simple. Rustic. Luxury.

Monterey VA

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A hot tub is featured at this cabin, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.

Hot Tub

Kitchen

Monterey Inn

32 W Main St Monterey VA

$209 nightly

$231 total

Apr 5 - Apr 6

Total with taxes and fees

This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. Concierge services are provided for your convenience.

Parking included

Free WiFi

Games Galore! Riverfront Group Retreat in McDowell

McDowell VA

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This vacation home features barbecue grills.

Pool

Kitchen

Solitude on 172 private acres in Highland County.

Doe Hill VA

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This vacation home featured laundry facilities and barbecue grills.

Kitchen

Washer

The Omni Homestead Resort & Spa

7696 Sam Snead Highway Hot Springs VA

Free Cancellation

Reserve now, pay when you stay

$304 nightly

$348 total

May 3 - May 4

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 mini golf, and families will appreciate the onsite laundry facilities.

Pool

Hot Tub

Marlinton Motor Inn

21507 Seneca Trl Marlinton WV

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$90 total

Apr 4 - Apr 5

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A seasonal outdoor pool is also provided.

Pool

Pet friendly

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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.

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Grayson Highlands State Park - Grayson County, VA

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 $518. 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.