Middlebrook Vacations from $495

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Middlebrook vacation packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Harrisonburg, VA - South

Motel 6 Harrisonburg, VA - South

2 out of 5
Price was $614, price is now $495 per person
$495
per person
Jan 5 - Jan 11
found 12 hours ago
Roundtrip non-stop flight included
Peoria (PIA) to Weyers Cave (SHD)
7.2/10 Good! (1,003 reviews)

Hotel Madison & Shenandoah Conference Ctr

Hotel Madison & Shenandoah Conference Ctr

3.5 out of 5
Price was $998, price is now $749 per person
$749
per person
Jan 5 - Jan 11
found 12 hours ago
Roundtrip non-stop flight included
Peoria (PIA) to Weyers Cave (SHD)
9.4/10 Exceptional! (1,229 reviews)

Massanutten Resort

Massanutten Resort

2.5 out of 5
Price was $642, price is now $524 per person
$524
per person
Jan 8 - Jan 10
found 24 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Weyers Cave (SHD)
8/10 Very Good! (1,634 reviews)
I already contacted management about a couple small things, but I would stay here again without hesitation. Overall good property and great amenities. Plus, the food didn’t feel like your typical ski resort concession food. That’s a huge plus!

Reviewed on Nov 2, 2026

Hotel 24 South

Hotel 24 South

3 out of 5
Price was $1,041, price is now $854 per person
$854
per person
Dec 23 - Dec 30
found 12 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Weyers Cave (SHD)
9.4/10 Exceptional! (1,254 reviews)

Mountainside Villas at Massanutten by Tripforth

Mountainside Villas at Massanutten by Tripforth

3.5 out of 5
Price was $1,236, price is now $1,026 per person
$1,026
per person
Jan 5 - Jan 11
found 12 hours ago
Roundtrip non-stop flight included
Peoria (PIA) to Weyers Cave (SHD)
9/10 Wonderful! (412 reviews)
Great place for a family to stay. Plenty of sleeping places and plenty of towels and linens. Will stay again.

Reviewed on Nov 2, 2026

Don't see what you're looking for?
See all available trips from Columbus to Middlebrook
View all trips

Middlebrook Hotel Deals

Motel 6 Staunton, VA

Motel 6 Staunton, VA

2 out of 5
96 Baker Lane Staunton VA
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $70 total per night from Nov 16 to Nov 17
$70 total
Nov 16 - Nov 17
Total with taxes and fees
Motel 6 Staunton, VA
Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street Staunton VA
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $126 total per night from Dec 1 to Dec 2
$126 total
Dec 1 - Dec 2
Total with taxes and fees
Hotel 24 South
Avid Hotel Staunton

Avid Hotel Staunton

2.5 out of 5
62 Sangers Lane Staunton VA
Fully refundable
$97 nightly
The price is $108 total per night from Nov 22 to Nov 23
$108 total
Nov 22 - Nov 23
Total with taxes and fees
9/10 Wonderful! (1,006 reviews)
"Very clean, next to a wonderful little restaurant with a great breakfast buffet. Bed and shower was FANTASTIC!"

Reviewed on Nov 1, 2026

Avid Hotel Staunton
See all 1,196 properties in Middlebrook
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.

Find the Best Middlebrook Vacation Packages

Middlebrook Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Shenandoah Valley Regional Airport (SHD)
Population
210
Top Sights
American Shakespeare Center, Rockbridge Vineyard and Mary Baldwin College

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Middlebrook vacation package cost?
You'll find cheap prices from $495 on Expedia for your Middlebrook getaway. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Middlebrook costs.
What are the cheapest months to go to Middlebrook?
You can usually find lower prices and better availability in December, January and February. Explore our cheap Middlebrook vacation packages and you could score some great off-season deals.
How many days is enough for Middlebrook?
With a well-organized travel plan, you can easily visit the most popular Middlebrook sights in a few days. But if you want to discover hidden spots or go on day tours, consider booking your Middlebrook vacation for longer.
How to find the best Middlebrook package deals?
Start your search for a Middlebrook package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Middlebrook package deal straight away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Middlebrook escape off to a flying start.
Is it cheaper to book a Middlebrook vacation as a package?
You can enjoy significant savings on your next Middlebrook getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Middlebrook?
If you're considering a spontaneous Middlebrook adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Middlebrook vacation packages?
Set off on your perfect escape to Middlebrook with Expedia's Book Now, Pay Later vacations. No need to save up or wait until payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to budget for your trip and snap up bargains while they last.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.