Photo by Brittany Davidson

Middlebrook Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Middlebrook

Valley Extended Suites
3.0 star property
9.0 out of 10, Wonderful, (158)
"Stayed one night... very clean and comfortable. Not a ton of dishes but kitchen was nice."
The price is AU$169
includes taxes & fees
6 Oct - 7 Oct
Valley Extended Suites
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, (253)
"This gorgeous townhouse was perfectly clean and very comfortable for our stay. The view is incredible! It is definitely a mountain getaway, so stock up on essentials before driving up there, but once you are there you won't be disappointed!!"
The price is AU$333
includes taxes & fees
3 Nov - 4 Nov
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
9.6 out of 10, Exceptional, (277)
"Stayed here with some friends on a quick golf trip and it was an ideal spot. The house is well-maintained and having 4 full sized beds worked out great. The host is an excellent communicator and was quick to answer any questions we had. "
The price is AU$608
includes taxes & fees
7 Oct - 8 Oct
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
View from the Top
10.0 out of 10, Exceptional, (42)
"Very nice "
View from the Top
Rustic Mountain Retreat-Bear Paw
9.8 out of 10, Exceptional, (212)
"We enjoyed our stay. We didn't have neighbors although there are cabins on either side so we were alone which was nice."
Rustic Mountain Retreat-Bear Paw
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
10.0 out of 10, Exceptional, (60)
"Stop wasting your time browsing other properties. If you’re looking for top notch hospitality then you’ll want to book your next trip with Lorraine!! She goes ABOVE & BEYOND with absolutely everything to make your stay incredibly special. A true Blue Ridge Mountain getaway doesn't get much sweeter than this one!"
The price is AU$294
includes taxes & fees
8 Oct - 9 Oct
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
9.8 out of 10, Exceptional, (61)
"Very comfortable well appointed house in an excellent location. The proximity of the AT and hikes we could walk to was greatly appreciated. The deck was wonderful…we utilized the gas fire pit every night. The trees blocked our view of mountains but we enjoyed listening to music and watching the squirrels. "
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
10.0 out of 10, Exceptional, (289)
"Enjoyed our stay. Property wa"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
The newest and largest edition to the Wintergreen Retreat portfolio!
9.6 out of 10, Exceptional, (34)
"We couldn’t have had a better weekend! Our host was very easy to communicate with and the house was beautiful. Would highly recommend for large gatherings. Proximity to outlooks and outdoor activities can’t be beat!"
The newest and largest edition to the Wintergreen Retreat portfolio!
Endless Mountain Top Views from All The Way Up!
10.0 out of 10, Exceptional, (45)
"Very clean, everything we needed was provided"
The price is AU$598
includes taxes & fees
6 Oct - 7 Oct
Endless Mountain Top Views from All The Way Up!
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
9.8 out of 10, Exceptional, (122)
"Wonderful, beautiful! This was our 3rd visit and we’ve already booked for next year."
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
WILDBRIAR LODGE • 6BR/6BA • MASTER SUITES • HOT TUB • GAME ROOM • MOUNTAIN VIEWS
9.6 out of 10, Exceptional, (13)
"Creative room layout-huge stone fireplace-very nice furnishings"
WILDBRIAR LODGE • 6BR/6BA • MASTER SUITES • HOT TUB • GAME ROOM • MOUNTAIN VIEWS
House / hot tub/pet friendly
9.8 out of 10, Exceptional, (56)
"We loved this place!! It was everything promised and exactly what we were hoping for!! Had a few questions for the host and she responded quickly and effectively! We definitely look forward to returning this winter for some skiing, wineries & hiking family time!!"
The price is AU$473
includes taxes & fees
6 Oct - 7 Oct
House / hot tub/pet friendly
Walk to Mtn Inn & The Market
9.6 out of 10, Exceptional, (24)
"We enjoyed our time. Highly recommended"
Walk to Mtn Inn & The Market
Meadow View Cabin, a deluxe log home near Lexington VA.
10.0 out of 10, Exceptional, (154)
"The property is beautiful, Relatively new. Clean. Close to Lexington."
Meadow View Cabin, a deluxe log home near Lexington VA.
Good Place Farms Upper Barn
9.2 out of 10, Wonderful, (10)
"Good Place should be great place. Wonderful location for family to gather and relax and enjoy the view, the stars, the clear air. Thanks"
The price is AU$2,986
includes taxes & fees
7 Oct - 8 Oct
Good Place Farms Upper Barn
Old Farm Road. Spacious house on 10 acres only 1 mile from downtown Lexington
9.8 out of 10, Exceptional, (51)
"Loved our stay in your home. "
Old Farm Road. Spacious house on 10 acres only 1 mile from downtown Lexington
Insane Mountain Views - New Listing
10.0 out of 10, Exceptional, (20)
"This property was the perfect space for us as we celebrated my mom’s 80th birthday with my siblings and our kids. The layout of the home couldn’t have been better. The views and amenities were outstanding! We’re already talking about when we can come back! We had 5 kids, ages 11-16, and they were comfortably spread out in the 2 bedrooms in the basement. The primary bedroom on the main floor was perfect for my parents. The four upstairs bedrooms were ideal for my brothers and our spouses. I...
Insane Mountain Views - New Listing
Stunning newly rebuilt home! Perfect peaceful getaway that sleeps 14!
10.0 out of 10, Exceptional, (45)
"We really enjoyed this house. Kids and friends loved to stay"
Stunning newly rebuilt home! Perfect peaceful getaway that sleeps 14!
Ski-In/Ski-Out Comfy Condo
10.0 out of 10, Exceptional, (17)
"My husband and I needed a relaxing get away and chose Wintergreen to escape some of the brutal heat. The condo was as represented including walking distance to restaurants and the nicely appointed market. Will definitely visit again."
Ski-In/Ski-Out Comfy Condo
Don't see what you're looking for?
See all available 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.
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Middlebrook you may be interested in

Sleep Inn Staunton
2.5 star property
9.2 out of 10, Wonderful, (1016)
"Great room for the price. Very small bathroom and shower but it was good for what we needed. "
The price is AU$131
includes taxes & fees
29 Oct - 30 Oct
Sleep Inn Staunton
Howard Johnson by Wyndham Lexington
2.0 star property
8.2 out of 10, Very good, (1415)
"Easy and friendly check in. Comfortable , clean and quiet room with a spectacular view of the mountains and sunset. Would definitely recommend. "
The price is AU$106
includes taxes & fees
7 Oct - 8 Oct
Howard Johnson by Wyndham Lexington
Wingate by Wyndham Waynesboro
2.5 star property
8.6 out of 10, Excellent, (644)
"Very good alternative to hotels nearby for less money."
The price is AU$134
includes taxes & fees
27 Oct - 28 Oct
Wingate by Wyndham Waynesboro
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.

Frequently asked questions

Can I find holiday rentals in Middlebrook?

Yes, there are holiday rentals close to the most popular sights in Middlebrook, or you can select a more secluded option if you're looking for a relaxing stay. Middlebrook is known for its parks.

What are some of the best holiday rentals that Middlebrook has to offer?

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.: This holiday home rental outside of Middlebrook is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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 George Washington National Forest. In the wider area, you’ll find Frontier Culture Museum and American Shakespeare Center.

What are holiday rentals like in Middlebrook?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlebrook. Holiday rentals offer amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.