Middlebrook Vacations from $380

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.
Hyatt Studios Harrisonburg

Hyatt Studios Harrisonburg

2.5 out of 5
Price was $438, price is now $380 per person
$380
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Weyers Cave (SHD)
9/10 Wonderful! (31 reviews)
This property is brand new so everything is in pristine condition.

Reviewed on May 10, 2026

Stable Craft Brewing & Cidery

Stable Craft Brewing & Cidery

2 out of 5
Price was $528, price is now $418 per person
$418
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Weyers Cave (SHD)
No reviews
Massanuttens Shenandoah Villas by Tripforth

Massanuttens Shenandoah Villas by Tripforth

4 out of 5
Price was $674, price is now $563 per person
$563
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Weyers Cave (SHD)
7.6/10 Good! (159 reviews)
The resort is very family friendly! Many parks, pools, so many activities! We had deer outside of our place daily it was great! The views were amazing. The only bad review is the cleanliness. I mean the walls were dirty, many cobwebs/dust. The floor needed a vacuum when we got there. A dead roach welcomed me when we walked into one of the rooms. They have a checkout checklist of things you need to do. I completely understand cleaning up after selves but it would be nice if the resort would make sure these villas are clean!

Reviewed on Mar 11, 2026

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

3.5 out of 5
Price was $454, price is now $388 per person
$388
per person
Jun 21 - Jun 24
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,005 reviews)
The renovations were well done while preserving the historical significance of the building. The 4th floor cupola offered beautiful 360 degree views of the surrounding area. Breakfast was not included in our booking - but the small & quaint bistro onsite called Second Draft offered really yummy breakfast options. We'll be back again!

Reviewed on May 10, 2026

Massanutten Resort

Massanutten Resort

2.5 out of 5
Price was $497, price is now $432 per person
$432
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Weyers Cave (SHD)
8/10 Very Good! (1,299 reviews)
Massanutten is a great place to stay, staff are friendly and there are some good activities.

Reviewed on May 5, 2026

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

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 May 31 to Jun 1
$124 total
May 31 - Jun 1
Total with taxes and fees
9.6/10 Exceptional! (1,127 reviews)
Hotel was in a good location and provided standard hotel accommodations. Staff was very friendly.

Reviewed on May 11, 2026

Hotel 24 South
Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
222 Jefferson Hwy Staunton VA
Fully refundable
$97 nightly
The price is $108 total per night from May 31 to Jun 1
$108 total
May 31 - Jun 1
Total with taxes and fees
9.2/10 Wonderful! (1,444 reviews)
Easy to get to. Nice building with friendly staff

Reviewed on May 10, 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
$59 nightly
The price is $67 total per night from May 24 to May 25
$67 total
May 24 - May 25
Total with taxes and fees
8.2/10 Very Good! (1,369 reviews)
Remodel was done as cheap as possible and it showed. Staff while not unfriendly, but not friendly. They didn’t feel approachable. Not a bad stay, but I wouldn’t go back either.

Reviewed on May 11, 2026

Howard Johnson by Wyndham Lexington
See all 1,188 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 $380 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.