Middlebrook Vacations from $398

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The Latest Middlebrook vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
Price was $450, price is now $398 per person
$398
per person
Aug 20 - Aug 23
found 22 hours ago
Roundtrip flight included
New York (NYC) to Weyers Cave (SHD)
8.2/10 Very Good! (1,004 reviews)
The 4th floor has a smell of vomit when you step off the elevator. The room themself were good, we stayed at a Holiday in Express in WV the room was very good.

Reviewed on Jun 18, 2026

The Summit at Massanutten Resort by Tripforth

The Summit at Massanutten Resort by Tripforth

3.5 out of 5
Price was $740, price is now $629 per person
$629
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Weyers Cave (SHD)
9.2/10 Wonderful! (80 reviews)
Massanutten is always my go to vacation spot! I love it!

Reviewed on Jun 16, 2026

Hotel 24 South

Hotel 24 South

3 out of 5
Price was $626, price is now $540 per person
$540
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Weyers Cave (SHD)
9.4/10 Exceptional! (1,171 reviews)
Great grand hotel, perfect place if you are going to the theater !

Reviewed on Jun 26, 2026

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

3.5 out of 5
Price was $616, price is now $534 per person
$534
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,008 reviews)
Room was a bit stuffy; to mediate it we were given a strange device which blew out cold air when ice was placed in it.

Reviewed on Jun 21, 2026

Massanutten's Regal Vistas by Tripforth

Massanutten's Regal Vistas by Tripforth

3.5 out of 5
Price was $979, price is now $855 per person
$855
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Weyers Cave (SHD)
8.8/10 Excellent! (68 reviews)
Best spring break Ever! Will definitely come back. Worth the price!

Reviewed on May 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
$111 nightly
The price is $124 total per night from Jul 12 to Jul 13
$124 total
Jul 12 - Jul 13
Total with taxes and fees
9.4/10 Exceptional! (1,172 reviews)
"Great grand hotel, perfect place if you are going to the theater !"

Reviewed on Jun 26, 2026

Hotel 24 South
Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
222 Jefferson Hwy Staunton VA
Fully refundable
$93 nightly
The price is $103 total per night from Jul 5 to Jul 6
$103 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (1,443 reviews)
"Clean, quiet and comfortable"

Reviewed on Jun 25, 2026

Sleep Inn Staunton
Howard Johnson by Wyndham Lexington

Howard Johnson by Wyndham Lexington

2 out of 5
2836 North Lee Highway Lexington VA
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $69 total per night from Jun 29 to Jun 30
$69 total
Jun 29 - Jun 30
Total with taxes and fees
8.2/10 Very Good! (1,379 reviews)
"Since the cost was so reasonable, we didn't expect it to be great - yet it was! Very clean, friendly staff, beautiful pool, beautiful scenery, good breakfast... waffles, bagels, cereal, yogurt, fruit, etc. Would definitely stay there again!"

Reviewed on Jun 26, 2026

Howard Johnson by Wyndham Lexington
See all 1,240 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 $398 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.