Highland County Holidays

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Top destinations in Highland County

Rural Virginia Farm country in Autumn in the valleys and hills of the Appalachian Mountains
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Monterey

Monterey

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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Our pick of the best Highland County Hotel Deals

Simple. Rustic. Luxury.

Simple. Rustic. Luxury.

Monterey VA
10/10 Exceptional! (188 reviews)
Great cabin in the hills of Virginia. The place was well cleaned and assessible. The hosts were friendly and helpful. Very pleased with my stay.

Reviewed on 8 Mar 2026

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Simple. Rustic. Luxury.
Monterey Inn

Monterey Inn

4 out of 5
32 W Main St Monterey VA
The price is NZ$355 per night from 16 Mar to 17 Mar
NZ$355
16 Mar - 17 Mar
includes taxes & fees
9.4/10 Exceptional! (43 reviews)
The room was nice and clean. there were flies comming in upstairs but that is truely typical of a house of this age. The owner had asked us to pay a couple of taxes that were not listed in the price (not sure it is ethical/legal/moral) - they close by 9 or you have to pay a $50 late fee A fee - no ...

Reviewed on 25 Feb 2026

Monterey Inn
Dog-Friendly, Riverfront 10BR w/ Games Galore

Dog-Friendly, Riverfront 10BR w/ Games Galore

McDowell VA
10/10 Exceptional! (5 reviews)
Amazing!
Our group had the most incredible time at this stunning riverfront retreat! From the moment we arrived, we were blown away by how spacious, welcoming, and beautifully appointed the home is. With 10 bedrooms and plenty of room for everyone, it was perfect for our multi-family getaway — and the views ...

Reviewed on 19 Feb 2026

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Dog-Friendly, Riverfront 10BR w/ Games Galore
See all 1,374 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.

Frequently asked questions

How much does a Highland County holiday package cost?
We make it simple to see the world, with Highland County packages starting from as little as . You'll have the flexibility to combine your preferred airlines, hotels and car rental. For the ultimate escape, why not add a couple of tours and activities to your travel itinerary?
How do I get a cheap travel package to Highland County?
Bundle your hotels and flights, add on extras such as activities or a rental car, and save with a Highland County holiday package. You won't just walk away with exciting discounts on your trip — you'll have loads of choice within your reach too. When you book through Expedia, you'll have your pick of over 550 partner airlines and 1 000 000 properties worldwide. Your affordable holiday starts right here, right now!
What are the top hotels in Highland County?
Apartment Atop An Old Country Store and Authentic Cabin With Fire Pit, 11mi To Trout Fishing know how to make their guests feel at home in Monterey. If you also plan to visit McDowell, have a look at Authentic Cabin With Fire Pit, 11mi To Trout Fishing and Cabin - Simple. Rustic. Luxury. Both are very popular with travellers.
How far in advance should I book my Highland County holiday?
While not all air carriers release tickets early, it's usually possible to look up international airfares on Expedia up to a year in advance. This is the time you'll score some incredible deals. If you're booking at the last minute, there's a chance you could get lucky. Low prices sometimes emerge only weeks before departure.
What does an Expedia Highland County travel package include?
Car rentals, hotels and flights — we connect you to the very best bargains. All you have to do is decide on your preferred combination. Once you've made your booking, you can add on the exciting stuff like day tours and sightseeing activities. Our travel packages make it simple to put together an awesome Highland County escape.
What should I know before booking a Highland County travel package?
Whether it's relaxation or adventure you're craving, a Highland County holiday package lets you organise your escape your way. Plus, you'll score great discounts when you combine your accommodation with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Highland County Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You can pick and choose your flights, hotels and more. We have more than 550 airline partners across the globe, so you have options galore when creating your Highland County getaway.
If I'm not able to travel, can I cancel my Highland County holiday package?
Your situation can change suddenly, so yes. You may be able to change or cancel your Highland County holiday package at no cost if you've booked in the last 24 hours. For bookings older than that, you can still make the necessary changes, but your hotel, car rental company or airline may charge additional fees. Want more information? Visit our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.