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Middlebrook Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Middlebrook vacation rentals

Standard Suite, 1 Queen Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.2 out of 10, Wonderful, (65 reviews)
"Very good value, would definitely stay again"
United States
Frank
$81 nightly
The price is $90
Jul 20 - Jul 21
Total with taxes and fees
Affordable Suites of America Waynesboro
Property grounds

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (68 reviews)
"Such a great little place! Quick drive to town, but far enough for a quiet night. Room had everything we needed (and then some) for a short stay, and all the animals were the sweetest added bonus. Would absolutely stay here again if we’re ever back in the area."
United States
Rebekah
$103 nightly
The price is $114
Jul 18 - Jul 19
Total with taxes and fees
The Firefly Springhouse
Smart TV

The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Buena Vista
9.8 out of 10, Exceptional, (38 reviews)
"We had a great stay at this property. It was very clean and had everything we needed for a pleasant experience. It’s a short walk away from a large field which was great when walking our dog."
United States
Alex S.
$160 nightly
The price is $178
Jul 16 - Jul 17
Total with taxes and fees
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Property grounds

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (110 reviews)
"Nice place!"
United States
Gregory G.
$238 nightly
The price is $267
Jul 16 - Jul 17
Total with taxes and fees
Endless Mountain Top Views from All The Way Up!
Exterior

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Montebello
10.0 out of 10, Exceptional, (64 reviews)
"We had a great stay at the Cabin! Everything met our expectations and more we will definitely be coming back!"
United States
Jake
$190 nightly
The price is $213
Jul 16 - Jul 17
Total with taxes and fees
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Property grounds

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (156 reviews)
"It was a beautiful stay - we enjoyed the place and wished we could have stayed one more day to soak up the surroundings of the area more!"
United States
Michelle W.
$220 nightly
The price is $247
Jul 16 - Jul 17
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Terrace/patio

Blair's Vintage Apartment Nestled in Wine Country

Blair's Vintage Apartment Nestled in Wine Country
Waynesboro
10.0 out of 10, Exceptional, (26 reviews)
"Had a fantastic time staying here. Apartment was super cozy and close to Shenandoah National Park. Deborah was a great hostess. "
United States
Matthew H.
$204 nightly
The price is $227
Jul 16 - Jul 17
Total with taxes and fees
Blair's Vintage Apartment Nestled in Wine Country
Fireplace

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (57 reviews)
"Very good host, good with communication! Nice clean place to stay and close to a lot of the places we were wanting to go!"
United States
Meredith T.
$190 nightly
The price is $213
Jul 21 - Jul 22
Total with taxes and fees
Where the Trail Ends
Exterior

New Blue RIdge Mountains Montebello, Virginia with stary stary skies

New Blue RIdge Mountains Montebello, Virginia with stary stary skies
Montebello
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful cabin in a lovely setting. Already planning another visit during warmer weather so we can take advantage of all the nearby outdoor activities."
United States
Michael C.
$188 nightly
The price is $211
Jul 16 - Jul 17
Total with taxes and fees
New Blue RIdge Mountains Montebello, Virginia with stary stary skies
Exterior

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Montebello
10.0 out of 10, Exceptional, (24 reviews)
"The cabin was Excellent!The communication with the owner was greatWe will stay again "
United States
Patrick G.
$190 nightly
The price is $213
Jul 16 - Jul 17
Total with taxes and fees
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Smart TV, DVD player, books, music library

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Roseland
10.0 out of 10, Exceptional, (108 reviews)
"Beautiful cabin!"
United States
Anna W.
$175 nightly
The price is $197
Jul 19 - Jul 20
Total with taxes and fees
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
1 bedroom, bed sheets

Remote Equipped Bell Tent Surrounded by Nature with Great Hiking Trails in Virginia

Remote Equipped Bell Tent Surrounded by Nature with Great Hiking Trails in Virginia
Mount Solon
$112 nightly
The price is $114
Jul 16 - Jul 17
Total with taxes and fees
Remote Equipped Bell Tent Surrounded by Nature with Great Hiking Trails in Virginia
Interior

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (31 reviews)
"Everything was perfect! "
United States
Danielle B.
$201 nightly
The price is $226
Jul 22 - Jul 23
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Exterior

New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail

New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail
Montebello
9.6 out of 10, Exceptional, (12 reviews)
"The property was very clean and located on scenic property. The owner provided many extra perks such as firewood, fire pit, grill, cooking materials, and several toiletries! Would definitely recommend this location to anyone!"
United States
Donna
$188 nightly
The price is $211
Jul 16 - Jul 17
Total with taxes and fees
New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail
Ravens Roost, 3 Bedrooms, Hot Tub, Mountain View | Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (20 reviews)
"Very quiet and peaceful stay. "
United States
Timika
$216 nightly
The price is $235
Jul 16 - Jul 17
Total with taxes and fees
Love Ridge Mountain Lodging
Property grounds

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Buena Vista
9.0 out of 10, Wonderful, (45 reviews)
"Great stay. Nice property in a very quiet neighborhood. "
United States
Kurtis W.
$177 nightly
The price is $204
Jul 16 - Jul 17
Total with taxes and fees
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Fridge, microwave, oven, stovetop

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Wintergreen Resort
10.0 out of 10, Exceptional, (41 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
$275 nightly
The price is $308
Jul 19 - Jul 20
Total with taxes and fees
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Exterior

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Wintergreen Resort
10.0 out of 10, Exceptional, (119 reviews)
"We loved staying at this apartment!"
United States
Sebastian A.
$280 nightly
The price is $314
Jul 19 - Jul 20
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (325 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
$241 nightly
The price is $271
Jul 26 - Jul 27
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (248 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
$114 nightly
The price is $127
Jul 19 - Jul 20
Total with taxes and fees
Valley Extended Suites
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.
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Top Middlebrook Hotel Reviews

Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

10/10 Excellent
"I like that it is right off the highway but hidden from the road,beds are comfortable,lots of tv channels to watch there is a dining room near the lobby that has food and drinks. I was tired so did not get a chance too have something in dining area As far as food places around probably a 12 minute drive Which has A Krogers, and gas station there but there is also a Walmart 15 minute drive . I did not like having to go downstairs for something to drink and snack the candy was 3 dollars and teas three fifty I only bought it there because I forgot to pick it up while at grocery store. There is. Fridge and microwave which I Loved."
Anita 1-night trip
Posted 5 hours ago
Holiday Inn Staunton Conference Center by IHG

Find out more about Middlebrook

Everything you need to know about Middlebrook vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebrook vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlebrook vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlebrook vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlebrook. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middlebrook in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlebrook rentals

At Expedia, we put the best Middlebrook vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlebrook rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlebrook vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlebrook. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Middlebrook?

Yes, we offer vacation rentals near top attractions in Middlebrook, or you can select a more secluded option if you'd like a relaxing place to stay. Middlebrook is known for its parks.

What are some of the best vacation rentals in Middlebrook?

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI: This vacation home rental outside of Middlebrook is located in the mountains and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the arcade game room in this rental home to help you unwind.

What can I see and do in Middlebrook?

While exploring the area, visit family-friendly sights like Beverley Cigar Store, or get outside and enjoy nature at Gypsy Hill Park. In the larger area, you’ll find Staunton Railroad Station and Frontier Culture Museum.

What are vacation rentals like in Middlebrook?

Vacation rentals are private accommodations you can reserve for a couple days or more in Middlebrook. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip.