Middlebrook Vacations from $465

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The Latest Middlebrook vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Staunton

Days Inn by Wyndham Staunton

2 out of 5
Price was $499, price is now $465 per person
$465
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Weyers Cave (SHD)
7.2/10 Good! (1,004 reviews)
Clean room friendly staff

Reviewed on Jan 26, 2026

Massanuttens Shenandoah Villas by Tripforth

Massanuttens Shenandoah Villas by Tripforth

4 out of 5
Price was $705, price is now $587 per person
$587
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Weyers Cave (SHD)
7.6/10 Good! (144 reviews)
Condo was clean. Jacuzzi tub needs updating. Everything else was good.

Reviewed on Dec 31, 2025

Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
Price was $535, price is now $483 per person
$483
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Weyers Cave (SHD)
8.2/10 Very Good! (1,002 reviews)
There was nothing exceptional, either good or bad, about the hotel. It was clean-ish, in an okay location, with okay amenities nearby. We tried to eat dinner at the 'restaurant' but after waiting 10 minutes and seeing absolutely no one anywhere, we left for a local pizza place instead. But the hotel kept us warm and dry overnight which was all we needed so it was . . . okay!

Reviewed on Jan 23, 2026

Massanutten Resort

Massanutten Resort

2.5 out of 5
Price was $608, price is now $553 per person
$553
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Weyers Cave (SHD)
8/10 Very Good! (1,093 reviews)
Clean apartments, very organized services,

Reviewed on Feb 2, 2026

Iris Inn and Cabins

Iris Inn and Cabins

4 out of 5
Price was $1,125, price is now $1,036 per person
$1,036
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Weyers Cave (SHD)
9.6/10 Exceptional! (7 reviews)
Incredible Mountain View at Sunset. Extremely comfortable bed. Delicious breakfast.

Reviewed on Nov 6, 2025

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Middlebrook Hotel Deals

Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street Staunton VA
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $129 total per night from Feb 10 to Feb 11
$129 total
Feb 10 - Feb 11
Total with taxes and fees
9.4/10 Exceptional! (1,081 reviews)
Yes the room was spotless

Reviewed on Jan 22, 2026

Hotel 24 South
Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
222 Jefferson Hwy Staunton VA
Fully refundable
$71 nightly
The price is $79 total per night from Feb 22 to Feb 23
$79 total
Feb 22 - Feb 23
Total with taxes and fees
9.2/10 Wonderful! (1,404 reviews)
Grande chambre très propre

Reviewed on Jan 31, 2026

Sleep Inn Staunton
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 Feb 14 to Feb 15
$70 total
Feb 14 - Feb 15
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
N/A

Reviewed on Jan 15, 2026

Motel 6 Staunton, VA
See all 1,165 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

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Frequently asked questions

How much does a Middlebrook vacation package cost?
You'll find cheap prices from $465 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.

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