Middlebrook Vacations from $501

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The Latest Middlebrook vacation packages

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

Grey Pine Lodge

2 out of 5
Price was $562, price is now $501 per person
$501
per person
Apr 8 - Apr 11
found 24 hours ago
Roundtrip flight included
New York (NYC) to Weyers Cave (SHD)
9.6/10 Exceptional! (114 reviews)
Pet friendly great grounds

Reviewed on Oct 17, 2025

Massanutten's Regal Vistas by Tripforth

Massanutten's Regal Vistas by Tripforth

3.5 out of 5
Price was $1,314, price is now $1,172 per person
$1,172
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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

Mountainside Villas at Massanutten by Tripforth

3.5 out of 5
Price was $1,055, price is now $950 per person
$950
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
9/10 Wonderful! (333 reviews)
Room exceeded our expectations, staff was very friendly

Reviewed on Jan 20, 2026

Massanuttens Shenandoah Villas by Tripforth

Massanuttens Shenandoah Villas by Tripforth

4 out of 5
Price was $1,018, price is now $918 per person
$918
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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

Gibson's Warehouse

Gibson's Warehouse

3.5 out of 5
Price was $902, price is now $822 per person
$822
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
9.8/10 Exceptional! (184 reviews)
This was our third time staying at Gibson's Warehouse. Huge room with kitchen and separate TV viewing area. Bed is very comfortable. Location is super. Just a few blocks to great wine bars (try Yelping Dog) and a great meal was had at Mill Street Restaurant. I highly recommend.

Reviewed on Jan 1, 2026

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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
$109 nightly
The price is $122 total per night from Feb 8 to Feb 9
$122 total
Feb 8 - Feb 9
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
$67 nightly
The price is $74 total per night from Feb 8 to Feb 9
$74 total
Feb 8 - Feb 9
Total with taxes and fees
9.2/10 Wonderful! (1,401 reviews)
Very nice. Short visit but had everything we needed.

Reviewed on Jan 21, 2026

Sleep Inn Staunton
Wingate by Wyndham Lexington

Wingate by Wyndham Lexington

2.5 out of 5
1100 N Lee Hwy Lexington VA
$84 nightly
The price is $97 total per night from Feb 2 to Feb 3
$97 total
Feb 2 - Feb 3
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
Perfect check in. Easy breakfast / nice place if you are visiting VMI

Reviewed on Jan 20, 2026

Wingate by Wyndham Lexington
See all 1,161 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 $501 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.