Middlebrook Vacation Rentals

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Our top choices for Middlebrook vacation rentals

Whimsical Creekside Cabin

Whimsical Creekside Cabin
Vesuvius
9.8 out of 10, Exceptional, (49 reviews)
"The cabin was very nice. "
United States
David F.
The price is CA $151
CA $326 total
includes taxes & fees
Apr 13 - Apr 14
Whimsical Creekside Cabin

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

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (105 reviews)
"Great stay with a fabulous view! Very cozy and comfortable! We had a wonderful little getaway!"
United States
Vicki E.
The price is CA $148
CA $345 total
includes taxes & fees
Mar 26 - Mar 27
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

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, (99 reviews)
"Highly recommend staying at this beautiful condo! The kitchen has everything you need, the views are breath-taking, the condo is very clean, and the hosts are very communicative and helpful. Will definitely stay here again the next time we travel to the area!"
United States
Allison N.
The price is CA $136
CA $367 total
includes taxes & fees
Mar 26 - Mar 27
Endless Mountain Top Views from All The Way Up!

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (51 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is CA $114
CA $157 total
includes taxes & fees
Mar 26 - Mar 27
The Firefly Springhouse

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, (149 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is CA $151
CA $341 total
includes taxes & fees
Mar 29 - Mar 30
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

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, (97 reviews)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is CA $178
CA $271 total
includes taxes & fees
Mar 26 - Mar 27
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

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, (13 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is CA $111
CA $299 total
includes taxes & fees
Mar 26 - Mar 27
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

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
9.6 out of 10, Exceptional, (17 reviews)
"Nice and cozy home for overnight stays "
United States
Yahima O.
The price is CA $137
CA $260 total
includes taxes & fees
Mar 30 - Mar 31
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

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)
"Place was great! Perfect getaway. "
United States
Bradley P.
The price is CA $199
CA $314 total
includes taxes & fees
Mar 26 - Mar 27
New Blue RIdge Mountains Montebello, Virginia with stary stary skies

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, (18 reviews)
"The cabin was Excellent!The communication with the owner was greatWe will stay again "
United States
Patrick G.
The price is CA $199
CA $314 total
includes taxes & fees
Mar 26 - Mar 27
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

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, (52 reviews)
"Great place to enjoy a cabin in the woods! "
United States
Brad E.
The price is CA $199
CA $314 total
includes taxes & fees
Mar 30 - Mar 31
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

The Pop Inn: Family Destination, Walk Dwntwn

The Pop Inn: Family Destination, Walk Dwntwn
Staunton
10.0 out of 10, Exceptional, (22 reviews)
"Great place- very clean & convenient"
United States
Susan B.
The price is CA $136
CA $315 total
includes taxes & fees
Mar 29 - Mar 30
The Pop Inn: Family Destination, Walk Dwntwn

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is CA $170
CA $274 total
includes taxes & fees
Mar 26 - Mar 27
Love Ridge Mountain Lodging

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
The price is CA $130
CA $383 total
includes taxes & fees
Mar 26 - Mar 27
Laurelwood Hollow: Walk to Ski & Swim

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (46 reviews)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
The price is CA $129
CA $321 total
includes taxes & fees
Mar 26 - Mar 27
The Modern Mountain Condo

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 CA $135
CA $309 total
includes taxes & fees
Mar 26 - Mar 27
Blair's Vintage Apartment Nestled in Wine Country

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
Verona
10.0 out of 10, Exceptional, (65 reviews)
"Everything was great! We enjoyed this stay immensely. "
United States
Deborah F.
The price is CA $261
CA $420 total
includes taxes & fees
Mar 31 - Apr 1
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

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, (316 reviews)
"Gorgeous view. Our fourth time here, and still a lovely place. "
United States
Elaine B.
The price is CA $142
CA $346 total
includes taxes & fees
Mar 26 - Mar 27
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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 CA $154
CA $257 total
includes taxes & fees
Mar 30 - Mar 31
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

Little Mountain Haven. True ski-in, ski-out. First floor!

Little Mountain Haven. True ski-in, ski-out. First floor!
Wintergreen Resort
10.0 out of 10, Exceptional, (9 reviews)
"Great little ski and ski out Property"
United States
Richard
The price is CA $80
CA $260 total
includes taxes & fees
Mar 26 - Mar 27
Little Mountain Haven. True ski-in, ski-out. First floor!
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

Find out more about Middlebrook

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlebrook. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Alone Mill Schoolhouse - A paradise for outdoor lovers: This vacation home rental outside of Middlebrook is located on the waterfront and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games 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 George Washington National Forest. 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.