Lodging Image

Middlebrook Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Middlebrook vacation rentals

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.2 out of 10, Wonderful, (61 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is ¥12,672
¥14,104 total
includes taxes & fees
Jun 14 - Jun 15
Affordable Suites of America Waynesboro

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

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (114 reviews)
"Great location"
United States
Chrissy R.
The price is ¥26,732
¥52,198 total
includes taxes & fees
Jun 16 - Jun 17
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!
Wintergreen Resort
10.0 out of 10, Exceptional, (165 reviews)
"Great location and great stay"
United States
Kellie S.
Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

Luxury Condo in the Sky! Finest in Wintergreen!

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (32 reviews)
"Amazing place with even more amazing views. Very comfortable and beautiful place. We had high expectations based on the pictures in the listing, and the place exceeded these high expectations. Fantastic place."
United States
missy s.
The price is ¥24,275
¥52,140 total
includes taxes & fees
Jul 7 - Jul 8
Luxury Condo in the Sky! Finest in Wintergreen!

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, (155 reviews)
"Lisa we are happy for staying at your places it awesome and we had great time, thank you let us use your home"
United States
Issac S.
The price is ¥17,645
¥39,632 total
includes taxes & fees
Jun 18 - Jun 19
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (36 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is ¥18,303
¥42,191 total
includes taxes & fees
Jun 15 - Jun 16
Wintergreen Condo -Steps to Ski and restaurants

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, (128 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
The price is ¥18,624
¥41,452 total
includes taxes & fees
Jun 16 - Jun 17
Escape to the Blue Ridge Mountains at Wine-tergreen!

Cozy Lux Condo at Wintergreen Resort

Cozy Lux Condo at Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (4 reviews)
"The place was great and we enjoyed our stay! Super comfy and cozy. Would definitely stay again!"
United States
Christopher H.
The price is ¥21,655
¥47,831 total
includes taxes & fees
Jun 14 - Jun 15
Cozy Lux Condo at Wintergreen Resort

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (44 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
The price is ¥22,316
¥46,697 total
includes taxes & fees
Jun 17 - Jun 18
Panoramic Peak: Wintergreen Condo with Views

Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is ¥46,560
¥88,346 total
includes taxes & fees
Jun 14 - Jun 15
Mountain Mindset

NEW! Cheerful 2 bd bungalow with hot tub. Must see!

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.8 out of 10, Exceptional, (56 reviews)
"Perfect for what we needed. "
United States
Matt & Jean
The price is ¥20,853
¥35,529 total
includes taxes & fees
Jul 1 - Jul 2
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

House / hot tub/pet friendly

House / hot tub/pet friendly
Tyro
9.8 out of 10, Exceptional, (74 reviews)
"Great location"
United States
Kim B.
The price is ¥31,280
¥51,341 total
includes taxes & fees
Jun 12 - Jun 13
House / hot tub/pet friendly

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (242 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is ¥16,641
¥18,521 total
includes taxes & fees
Jun 14 - Jun 15
Valley Extended Suites

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (38 reviews)
"Very organized information and amazing communication from host ahead of arrival; the view and location are amazing, and the accommodations were comfortable and made for an easy and fun adventure! Will definitely stay here again. "
United States
Blayre G.
The price is ¥24,366
¥63,431 total
includes taxes & fees
Jun 14 - Jun 15
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

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, (323 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is ¥20,374
¥45,596 total
includes taxes & fees
Jun 22 - Jun 23
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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, (105 reviews)
"Great hosts, place is in great conditions with all needed amenities. Very seamless and easy checkin and checkout process."
United States
Eric R.
The price is ¥17,635
¥44,684 total
includes taxes & fees
Jun 25 - Jun 26
Endless Mountain Top Views from All The Way Up!

Lofty Pursuits: Spectacular View + EV Charger

Lofty Pursuits: Spectacular View + EV Charger
Treeloft
10.0 out of 10, Exceptional, (20 reviews)
"We had an amazing stay!"
United States
Billy K.
The price is ¥27,133
¥66,500 total
includes taxes & fees
Jun 16 - Jun 17
Lofty Pursuits: Spectacular View + EV Charger

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (66 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
The price is ¥13,294
¥18,371 total
includes taxes & fees
Jun 14 - Jun 15
The Firefly Springhouse

New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen
Chestnut Springs
10.0 out of 10, Exceptional, (14 reviews)
"Perfect place - thank you so much for letting us borrow your home!"
United States
Suzanne Z.
New Build! Log Cabin with Hot Tub in Wintergreen

Swannanoa Guest House

Swannanoa Guest House
2.0 star property
Afton
The price is ¥47,963
¥106,798 total
includes taxes & fees
Jun 30 - Jul 1
Swannanoa Guest House
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

Top Middlebrook Hotel Reviews

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:

  • View our selection of featured holiday rentals in Middlebrook
  • Use the map to find apartments and other holiday homes in the Middlebrook neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlebrook while they last

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?

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 Sunspots Studios Glassblowing, 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.