Middlebrook Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Middlebrook vacation rentals

Exterior

Whimsical Creekside Cabin

Whimsical Creekside Cabin
Vesuvius
10.0 out of 10, Exceptional, (53 reviews)
"Lovely cabin with great amenities"
United States
Austin L.
The price is ￥17,532
￥37,305 total
includes taxes & fees
May 12 - May 13
Whimsical Creekside Cabin
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, (23 reviews)
"Nice and cozy home for overnight stays "
United States
Yahima O.
The price is ￥15,938
￥30,156 total
includes taxes & fees
Apr 27 - Apr 28
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
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, (100 reviews)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is ￥20,719
￥31,323 total
includes taxes & fees
Apr 29 - Apr 30
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Standard Suite, 1 Queen Bed | Private kitchen | Full-size fridge, microwave, oven, stovetop

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (55 reviews)
"Friendly staff "
United States
Kyle
The price is ￥13,229
￥14,724 total
includes taxes & fees
May 3 - May 4
Affordable Suites of America Waynesboro
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, (102 reviews)
"The mountain views from the balcony are spectacular!"
United States
Becca R.
The price is ￥10,690
￥35,271 total
includes taxes & fees
Apr 27 - Apr 28
Endless Mountain Top Views from All The Way Up!
Exterior detail

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Waynesboro
10.0 out of 10, Exceptional, (20 reviews)
"The perfect stay for a wedding weekend in Waynesboro. It was very warm and accommodating and I can’t say enough good things about it. Thank you for a great weekend"
United States
Michael W.
The price is ￥17,930
￥29,713 total
includes taxes & fees
Apr 27 - Apr 28
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Property grounds

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (57 reviews)
"The room was very clean and conveniently located for us."
United States
Jeanell S.
The price is ￥13,197
￥18,237 total
includes taxes & fees
Apr 27 - Apr 28
The Firefly Springhouse
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, (57 reviews)
"Beautiful location, great hosts, perfect trip. If you’re looking for a quiet getaway, this is the place. "
United States
Adam L.
The price is ￥23,110
￥35,975 total
includes taxes & fees
Apr 30 - May 1
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Fridge, microwave, oven, stovetop

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (35 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
The price is ￥16,496
￥48,775 total
includes taxes & fees
Apr 27 - Apr 28
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Property grounds

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (14 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is ￥12,910
￥34,186 total
includes taxes & fees
Apr 27 - Apr 28
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
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, (152 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is ￥17,532
￥38,483 total
includes taxes & fees
Apr 27 - Apr 28
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
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, (20 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.
The price is ￥23,110
￥35,797 total
includes taxes & fees
Apr 27 - Apr 28
New Blue RIdge Mountains Montebello, Virginia with stary stary skies
Exterior

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (31 reviews)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
The price is ￥17,213
￥51,725 total
includes taxes & fees
Apr 27 - Apr 28
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
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, (37 reviews)
"Great stay. Nice property in a very quiet neighborhood. "
United States
Kurtis W.
The price is ￥11,332
￥30,523 total
includes taxes & fees
Apr 29 - Apr 30
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Exterior

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

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Montebello
9.8 out of 10, Exceptional, (19 reviews)
"Heat works great. Very pet friendly. "
United States
Barbara L.
The price is ￥23,110
￥35,975 total
includes taxes & fees
Apr 27 - Apr 28
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Exterior

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (108 reviews)
"Very nice, updated place with everything we needed. We would definitely stay here again!"
United States
Kimberly M.
The price is ￥21,516
￥45,104 total
includes taxes & fees
Apr 27 - Apr 28
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
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
9.4 out of 10, Exceptional, (9 reviews)
"Very nice quaint cabin with lovely river access, close to crabtree falls. We truly enjoyed our stay and hope to return. "
United States
Julia D.
The price is ￥23,110
￥35,797 total
includes taxes & fees
Apr 27 - Apr 28
New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail
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, (23 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.
The price is ￥15,619
￥35,122 total
includes taxes & fees
Apr 27 - Apr 28
Blair's Vintage Apartment Nestled in Wine Country
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, (30 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
The price is ￥19,126
￥38,661 total
includes taxes & fees
Apr 27 - Apr 28
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Fireplace

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (49 reviews)
"Great place to stay to hit the ski slopes. Just a short walk to the slopes and right next to the gas station/ small grocery shop to easily pick up some food on the way back from skiing. "
United States
Joyce B.
The price is ￥15,026
￥36,561 total
includes taxes & fees
Apr 27 - Apr 28
The Modern Mountain Condo
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

Days Inn by Wyndham Waynesboro

Days Inn by Wyndham Waynesboro

2/10 Terrible
"The room had stains and tears throughout the room . The bathroom did not look very clean at all. There were brown stains on the ceiling that looked like oil marks ,brown rings in the sink and tub…holes and tears all over the floor- I would not go there again. To say it was just run down is an understatement."
Karen 1-night trip
Posted 1 hour ago
Days Inn by Wyndham Waynesboro

Find out more about Middlebrook

Search for holiday rentals in Middlebrook on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlebrook using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middlebrook!

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?

HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome: This vacation home rental outside of Middlebrook is located in the mountains and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Frontier Culture Museum and American Shakespeare Center.

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.