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Middlebrook Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Middlebrook

Studio Suite | Private kitchen | Full-size fridge, microwave, oven, stovetop
Valley Extended Suites

Valley Extended Suites

3.0 star property
Fishersville
9.0 out of 10, Wonderful, (216)
"I liked the cleanliness of the suite, the fully staffed kitchen, the large bathroom, the comfortable bed, the ease and safety of the parking area."
United States
Tammy
The price is ￥17,679
￥19,677 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Valley Extended Suites
Apartment, Private Bathroom (The Bohemian Suite) | Lobby
The Bohemian Suite

The Bohemian Suite

2.0 star property
Staunton
10.0 out of 10, Exceptional, (6)
"It was really nice. A bit pricey. "
United States
Bonny
The price is ￥13,802
￥24,763 total
includes taxes & fees
Dec 16 - Dec 17
The Bohemian Suite
Property grounds
Whimsical Creekside Cabin

Whimsical Creekside Cabin

Vesuvius
9.8 out of 10, Exceptional, (39)
"Had a very quiet relaxing stay "
United States
Joyce I.
The price is ￥11,867
￥29,781 total
includes taxes & fees
Dec 7 - Dec 8
Whimsical Creekside Cabin
Standard Suite, 1 Queen Bed | Living area | LCD TV, DVD player
Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro

2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (53)
"Always a pleasant stay."
United States
MARJORIE
The price is ￥12,251
￥13,636 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Affordable Suites of America Waynesboro
Interior
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, (19)
"Beautiful home, very comfortable, and uniquely fun decor. Highly recommend!"
United States
Melissa
The price is ￥14,660
￥25,814 total
includes taxes & fees
Dec 18 - Dec 19
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Smart TV, fireplace, books
Stylish-Updated-Central -Walk to Slopes-Dogs OK!

Stylish-Updated-Central -Walk to Slopes-Dogs OK!

Wintergreen Resort
9.8 out of 10, Exceptional, (27)
"Great little place for family to rest after long days of hiking!"
United States
joseph G.
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
Exterior
Little Yellow House: Walk to Downtown Staunton

Little Yellow House: Walk to Downtown Staunton

Staunton
10.0 out of 10, Exceptional, (6)
"I loved the location and the extra amenities !"
United States
Miriam
The price is ￥15,358
￥43,959 total
includes taxes & fees
Dec 7 - Dec 8
Little Yellow House: Walk to Downtown Staunton
Outdoor dining
Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!

Wintergreen Resort
9.8 out of 10, Exceptional, (123)
"The condo was very nice. Located on top of the mountain resort having spectacular views for the outlook just a short walk away. We will be boocking again for our next trip. "
United States
John
The price is ￥16,614
￥38,343 total
includes taxes & fees
Dec 7 - Dec 8
Escape to the Blue Ridge Mountains at Wine-tergreen!
Interior
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

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

2.0 star property
Wintergreen Resort
10.0 out of 10, Exceptional, (24)
"The property is extremely clean, well decorated and stocked. We had a fantastic time and absolutely would stay here again. "
United States
Cassie H.
The price is ￥20,943
￥52,265 total
includes taxes & fees
Dec 7 - Dec 8
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Property grounds
Blair's Vintage Apartment Nestled in Wine Country

Blair's Vintage Apartment Nestled in Wine Country

Waynesboro
10.0 out of 10, Exceptional, (22)
"Clean and vitage style type of apartment. Nice for a quiet stay."
United States
Darrell C.
The price is ￥15,198
￥35,039 total
includes taxes & fees
Dec 20 - Dec 21
Blair's Vintage Apartment Nestled in Wine Country
Fridge, microwave, oven, dishwasher
Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail

2.0 star property
Roseland
8.4 out of 10, Very Good, (9)
"I contacted the owners to see if my family and I could check in earlier and they were about to accommodate for us. The home was clean, spacious, and had everything we needed for our stay."
United States
Sa'Mone M.
The price is ￥17,840
￥45,296 total
includes taxes & fees
Dec 7 - Dec 8
Bluebird Cottage: Near 151 + Appalachian Trail
Cabin, Private Bathroom (Blackwood Chalet) | Exterior
Blackwood Chalet

Blackwood Chalet

2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3)
"Love the area"
United States
Toni
The price is ￥26,217
￥60,468 total
includes taxes & fees
Dec 7 - Dec 8
Blackwood Chalet
Exterior
The Firefly Springhouse

The Firefly Springhouse

Staunton
9.8 out of 10, Exceptional, (43)
"Great cottage for 2 and peaceful setting. Host was helpful with great dinner recommendations "
United States
Joseph
The price is ￥12,845
￥17,750 total
includes taxes & fees
Dec 6 - Dec 7
The Firefly Springhouse
Dining
Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge

Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge

2.0 star property
Fairfield
10.0 out of 10, Exceptional, (10)
"We had a great little break from the hustle and bustle of life. We are locals and it was nice to just get away for a few days"
United States
Don P.
The price is ￥16,909
￥77,450 total
includes taxes & fees
Dec 8 - Dec 9
Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge
Terrace/patio
The Overlook: Walk Downtown + City Views

The Overlook: Walk Downtown + City Views

Staunton
10.0 out of 10, Exceptional, (29)
"House was nicely decorated, great location to town, and had all the amenities you would need to stay. "
United States
Stephanie P.
The price is ￥18,455
￥39,081 total
includes taxes & fees
Dec 7 - Dec 8
The Overlook: Walk Downtown + City Views
Exterior
The Pop Inn: Family Destination, Walk Dwntwn

The Pop Inn: Family Destination, Walk Dwntwn

Staunton
10.0 out of 10, Exceptional, (17)
"We had a great stay at The Pop Inn. Very clean, good location, check-in and check-out were a breeze and all we needed for cooking simple meals was provided. "
United States
Janelle B.
The price is ￥15,353
￥34,564 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Pop Inn: Family Destination, Walk Dwntwn
Hanging Rock Cabin, 2 Bedrooms, Jetted Tub, Mountain View | Terrace/patio
Love Ridge Mountain Lodging

Love Ridge Mountain Lodging

3.0 star property
Montebello
10.0 out of 10, Exceptional, (13)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is ￥27,032
￥39,667 total
includes taxes & fees
Dec 8 - Dec 9
Love Ridge Mountain Lodging
Interior
Staunton Underground: Center of Downtown

Staunton Underground: Center of Downtown

Staunton
9.6 out of 10, Exceptional, (42)
"Great location, close to town. We could hear people walking around upstairs but overall it was a comfortable stay in Staunton "
United States
Cyndy S.
The price is ￥13,802
￥36,301 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Staunton Underground: Center of Downtown
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, (301)
"Great view!!"
United States
Suzanne W.
The price is ￥13,822
￥34,687 total
includes taxes & fees
Dec 10 - Dec 11
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Property grounds
The Modern Mountain Condo

The Modern Mountain Condo

Wintergreen Resort
10.0 out of 10, Exceptional, (33)
"Fantastic stay at the Modern Mountain Condo! The check-in process was a breeze, the location is exactly as pictured and was very clean. Spacious location for a couples getaway. Host was extremely responsive to any questions and provided us great instructions and details about the space. Will stay again in the future! "
United States
Kelsey N.
The price is ￥15,532
￥37,303 total
includes taxes & fees
Dec 7 - Dec 8
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

Wingate by Wyndham Lexington

Wingate by Wyndham Lexington

10/10 Excellent
"Very nice front desk"
Ellen 1-night trip
Posted 1 day ago
Wingate by Wyndham Lexington

Find out more about Middlebrook

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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 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.