Photo by Brittany Davidson

Middlebrook Holiday Rentals

Holiday Rentals in Middlebrook

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (171)
"We have stayed here twice in the last two months. Both rooms were immaculately clean! Front office staff was pleasant and accommodating both times (It was the same woman both times...I just can't remember her name. ) If you are going to stay here, you so need to bring a hair dryer, conditioner (shampoo is provided), creamer( if you don't like French vanilla)"
The price is AU$171
includes taxes & fees
3 Dec - 4 Dec
Valley Extended Suites

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (256)
"My wife Teresa and I have been staying here for 11 years now. Every year for the last eleven years we have stayed the last week of Oct. The view is incredible. It never gets old. Something else that is very important to my wife and I is that the foyer door is only about 15 feet from the parking lot and its a flat walkway. Also, once in the foyer, its literally 2 steps to the stairs which are only 9 stairs. Most condos at Wintergreen are a hike just getting to the front door of the unit. Not...
The price is AU$430
includes taxes & fees
30 Nov - 1 Dec
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

10.0 out of 10, Exceptional, (65)
"The cabin is super cute and close to breweries. We had a great time and the host is amazing! "
The price is AU$309
includes taxes & fees
26 Nov - 27 Nov
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (283)
"We came to stay in this area to attend my best friend's wedding. There were around 100 guests at the wedding and everyone had rented a home in the area. Our location was perfect! We were near other guests, the venue, and several breweries. There were several activities planed at the resort as well. We were able to spend one day in Charlottesville as well but it was around a 50 minute drive. We really enjoyed the view and trails around the home. There are several balconies to relax on but we...
The price is AU$596
includes taxes & fees
1 Dec - 2 Dec
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (51)
"This was our second time at this location. It is well equipped, clean, comfortable and the location is great. It sits at the top of the ridge, so views of sunrise and the evening sky are beautiful. The owners are responsive and accommodating. We "
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, (123)
"This lovely little cottage on the piney river was the perfect place to celebrate 35 years of marriage. The setting was beautiful and the accommodations spacious yet intimate. The cottage demonstrates an obvious history of love and good memories. We fished the section of river assigned and got skunked. The beauty of the setting was more than compensation for this disappointment. The owners have set up a welcoming, warm and friendly vibe that made it a pleasure to stay at Sycamore Shade. We...
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

9.8 out of 10, Exceptional, (62)
"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!

View from the Top

10.0 out of 10, Exceptional, (45)
"We really enjoyed our stay and the wonderful mountain vews! Very comfortable condo."
View from the Top

Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

9.8 out of 10, Exceptional, (16)
"Our weekend was easily a 9;8 (a number we saw posted in the info you provided)...and we look forward to returning to this exact location...We loved the quality, uniqueness, and location of Traveler's Rest.....The weekend was as near perfect as it gets with the Condo, the food at The Echo, and the weather...The food and service at The Echo was excellent and deserves a higher rating than we saw...Denise and I had a really special experience, one that we won't forget...."
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

Rustic Mountain Retreat-Bear Paw

9.8 out of 10, Exceptional, (218)
"Awesome location for hiking. Backyard River is beautiful!"
Rustic Mountain Retreat-Bear Paw

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (296)
"The property is very well maintained. The host is amazing, she makes sure that you have most of what you may need stocked in the condo. The condo was so peaceful that me and my wife didn't want to leave."
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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

10.0 out of 10, Exceptional, (25)
"The rustic cabin was absolutely gorgeous with well thought out amenities and activities. The setting is serene and peaceful. The owner was incredibly thoughtful in creating our perfect stay. "
The price is AU$336
includes taxes & fees
8 Dec - 9 Dec
Charming Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

Perfect Getaway for Vacation or Staycation!!

10.0 out of 10, Exceptional, (17)
"A tiny condo with owner Who was reluctant to give me the code to the front door within two days of arrival. He said, « I already gave it to you », but I could not find it and he continued that same dialogue until the following day – with one .day before arrival.. The kitchen was wonderful"
Perfect Getaway for Vacation or Staycation!!

HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome

10.0 out of 10, Exceptional, (81)
"First, the host Alex, is incredible! Stayed in contact before, right after we checked in to be sure all was good and right after we checked out. GOLD star Alex!! The property was incredible! Nice surprise was the soft water system. Fire pit was very nice as well. Kitchen well appointed and clean. Memory foam mattresses and extremely comfortable. Property secluded and private. All in all…6 stars in my book!!"
HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome

Time to Book for Fall and Winter...Amazing Views and 5-Star Amenities

10.0 out of 10, Exceptional, (292)
"Very clean, super easy check in and out process, great guides and instructions for how to use the house, and a fully stocked kitchen. We loved it all! It is a second floor condo with people above, so if you are a light sleeper, just know that you can sometimes hear the people above. We’d def recommend to friends. "
Time to Book for Fall and Winter...Amazing Views and 5-Star Amenities

Old Farm Road. Spacious house on 10 acres only 1 mile from downtown Lexington

9.8 out of 10, Exceptional, (55)
"It was another enjoyable stay. The comfort and convenience of the house made for a wonderful family weekend! "
Old Farm Road. Spacious house on 10 acres only 1 mile from downtown Lexington

Elegant & Modern Carriage House at Twin Maple Farm

10.0 out of 10, Exceptional, (183)
"We enjoyed every minute of our stay. Loved being able to watch the sun rise from our bedroom balcony and then watch the sunset from the front porch. Loved seeing the cows walk down to their watering hole and especially enjoyed watching Jasper their horse roam the pasture. We would stay again the next time we are in the area. "
The price is AU$335
includes taxes & fees
1 Dec - 2 Dec
Elegant & Modern Carriage House at Twin Maple Farm

The newest and largest edition to the Wintergreen Retreat portfolio!

9.6 out of 10, Exceptional, (36)
"Me and friends had an amazing time at this mountain retreat! Loved the location and beautiful area. The house is spectacular too! Highly recommend "
The newest and largest edition to the Wintergreen Retreat portfolio!

Luxury cabin in the woods, 2 bedrooms plus loft

10.0 out of 10, Exceptional, (156)
"My husband & I went to celebrate our 29th Wedding Anniversary on November 18th. This cabin was the cleanest, most beautiful place we have ever been to! There wasn't 1 day that we weren't in awe by all the deer and the peacefulness of this place! We will definitely be going back whether just the two of us or with friends and family! They had everything you could think of provided in every room! They even bought us Roses and a card for our anniversary! They did not have to do that, and it was...
Luxury cabin in the woods, 2 bedrooms plus loft

Ski-In/Ski-Out Comfy Condo

10.0 out of 10, Exceptional, (19)
"Unit was very clean. Kitchen was well stocked. Neighbor upstairs was very noisy. Bed was not very comfortable. Otherwise nice and cozy. "
Ski-In/Ski-Out Comfy 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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Other types of properties in Middlebrook you may be interested in

Howard Johnson by Wyndham Lexington

2.0 star property
8.2 out of 10, Very good, (1448)
"Just spent the overnight at the room. It was very clean."
The price is AU$112
includes taxes & fees
27 Nov - 28 Nov
Howard Johnson by Wyndham Lexington

Motel 6 Staunton, VA

2.0 star property
7.8 out of 10, Good, (1096)
"Easy off and on the 81. Quiet location very nice front desk staff member. "
The price is AU$100
includes taxes & fees
26 Nov - 27 Nov
Motel 6 Staunton, VA

Wingate by Wyndham Waynesboro

2.5 star property
8.6 out of 10, Excellent, (713)
"Breakfast staff were friendly and conscientious! The hotel was just fine. The large room was very clean, but grey and dark and rather minimalistic, so it was a bit depressing, but otherwise, fine. "
The price is AU$131
includes taxes & fees
1 Dec - 2 Dec
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 an outdoor pool, a fireplace 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. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 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.