Name: Simple. Rustic. Luxury.
Rating: 9.8

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

Every year, for two weekends in March, Highland County, VA is host to the Maple Festival. People come from all over the area to eat a pancake breakfast, learn about making maple syrup, buys crafts, food, and other goods from Appalachian artists, and just enjoy the beginning of spring. This particular guy has been there every year I've been, and is always drawing a crowd as he explains to everyone his craft and how it is done. #market

The Latest Highland County Vacation Packages

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

Holiday Inn Staunton Conference Center by IHG

$305

per person

Feb 28 - Mar 4

found 11 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Weyers Cave (SHD)

8.2/10 Very Good! (1,002 reviews)

A premier place to spend the night in comfort and quiet. Great location beautiful hotel

Reviewed on Jan 4, 2026

Hotel Madison & Shenandoah Conference Ctr

$755

per person

Feb 13 - Feb 15

found 1 day ago

Roundtrip non-stop flight included

Norfolk (ORF) to Weyers Cave (SHD)

9.2/10 Wonderful! (1,031 reviews)

Spacious room with a great view. The lobby was decorated beautifully for Christmas. Able to walk to downtown for meals and shopping.

Reviewed on Jan 2, 2026

Massanutten's Regal Vistas by Tripforth

Save 100% on your flight

$536

per person

Feb 28 - Mar 4

found 11 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Weyers Cave (SHD)

8.8/10 Excellent! (58 reviews)

Everything was amazing! Very clean

Reviewed on Dec 31, 2025

Mountainside Villas at Massanutten by Tripforth

$388

per person

Feb 28 - Mar 4

found 11 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Weyers Cave (SHD)

9/10 Wonderful! (333 reviews)

Pros- Beautiful view, nice amenities such as jacuzzi anbs sauna) and plenty of space for a family to spread out. Cons- Cleaning could be better (laundry machine still had clumps of used detergent, hair on the floor and furniture) and some appliances are old and not working properly (coffee maker was leaking, microwave was glitching) minimal cookware and kitchen equipment.

Reviewed on Jan 2, 2026

Massanutten's Woodstone Meadows by Tripforth

$459

per person

Feb 28 - Mar 4

found 11 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Weyers Cave (SHD)

9/10 Wonderful! (219 reviews)

The room was spotless and hostesses were excellent .

Reviewed on Nov 6, 2025

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)

Wood burning fireplace was vreat!! Loved the vibesand serenity. Thank you!

Reviewed on Nov 16, 2025

Get rates

The Omni Homestead Resort & Spa

7696 Sam Snead Highway Hot Springs VA

Fully refundableReserve now, pay when you stay

$306 nightly

$349 total

Jan 19 - Jan 20

Total with taxes and fees

8.6/10 Excellent! (991 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

$90 total

Jan 10 - Jan 11

Total with taxes and fees

8.2/10 Very Good! (1,000 reviews)

Friendly front desk staff, mostly clean room except for a couple hairs in the bathtub and on the bathroom sink. The beds were comfy and the room was spacious. Very affordable price for a one-night stay for two people

Reviewed on Dec 22, 2025

See all 1,354 properties in Highland County

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.