Middlebrook Vacations from $806
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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
$806
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
8.2/10 Very Good! (1,004 reviews)
The hotel room was clean and comfortable. We stayed two nights and did need some more clean towels which we thought would be replenished
Reviewed on Aug 11, 2026
The Blackburn Inn and Conference Center
$912
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,003 reviews)
Unusual space in its current incarnation. Nicely appointed, very comfortable, cupola is an experience to climb and look out from, supports excellent local artists, deep history. Currently very nicely Maintained.
Reviewed on Aug 13, 2026
Hotel 24 South
$958
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
9.4/10 Exceptional! (1,204 reviews)
Es un hotel antiguo, muy acogedor. La habitación muy limpia. Excelente ubicación. El desayuno podría mejorar por lo que cobran.
Reviewed on Aug 13, 2026
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Howard Johnson by Wyndham Lexington
2836 North Lee Highway Lexington VA
Fully refundableReserve now, pay when you stay
$58 nightly
$67 total
Aug 20 - Aug 21
Total with taxes and fees
Hotel 24 South
24 South Market Street Staunton VA
Fully refundableReserve now, pay when you stay
$104 nightly
$116 total
Sep 3 - Sep 4
Total with taxes and fees
9.4/10 Exceptional! (1,203 reviews)
"Es un hotel antiguo, muy acogedor. La habitación muy limpia. Excelente ubicación. El desayuno podría mejorar por lo que cobran."
Reviewed on Aug 13, 2026
Holiday Inn Staunton Conference Center by IHG
152 Fairway Lane Staunton VA
Fully refundable
$106 nightly
$118 total
Sep 13 - Sep 14
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"The hotel room was clean and comfortable. We stayed two nights and did need some more clean towels which we thought would be replenished"
Reviewed on Aug 11, 2026
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 $806 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.
