Photo by Brittany Davidson

Holiday Rentals in Middlebrook

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Holiday Rentals in Middlebrook

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

9.0 out of 10, Wonderful, (267)
"Overall our stay was great, the place had a great view and was super clean, the property managers were easy to reach as well! Two things to note i would suggest bringing a throw blanket if you get cold easily as there were no extras, also the hot tub mentioned in the comments is actually just the master bed rooms tub! "
The price is €235
includes taxes & fees
3 Mar - 4 Mar
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (174)
"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 €121
includes taxes & fees
12 Mar - 13 Mar
Valley Extended Suites

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

9.6 out of 10, Exceptional, (294)
"Perfect ski weekend rental. Great communication with Scott. Kitchen is nicely equipped. Hot tub is hot and was perfect for soaking and relaxing after a great day of skiing."
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (11)
"The cabin was very nicely set up, clean, and comfortable. The property manager was in constant contact with me to make sure I had everything I needed. I would highly recommend this place to anyone looking for a quiet relaxing escape. "
The price is €259
includes taxes & fees
4 Mar - 5 Mar
Love Ridge Mountain Lodging

New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

9.4 out of 10, Exceptional, (121)
"Well stocked kitchen, , clean, firewood provided, close to mountain!! would come back again"
The price is €234
includes taxes & fees
26 Mar - 27 Mar
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

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

10.0 out of 10, Exceptional, (33)
The price is €230
includes taxes & fees
27 Feb - 28 Feb
Charming Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

Wintergreen Condo -Steps to Ski and restaurants

9.8 out of 10, Exceptional, (10)
"Best price and a perfect little condo just a short walk to the ski lifts. An old man, 3 teenagers, and my mini me, truly enjoyed it. It has all you need to cook and chill out after a long day on the slopes. The fireplace with a constant supply of wood was the sugar on top. Thanks for a great stay."
The price is €232
includes taxes & fees
27 Feb - 28 Feb
Wintergreen Condo -Steps to Ski and restaurants

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (61)
"This is a very nice condo, very clean, nicely decorated, and with a great view. I would definitely stay here again "
The price is €332
includes taxes & fees
9 Mar - 10 Mar
Endless Mountain Top Views from All The Way Up!

Whimsical Creekside Cabin

10.0 out of 10, Exceptional, (17)
"My kids and I wanted to do something special during our midwinter break from homeschooling, so we booked a cabin. We were so lucky to find this one! It has a creek and is nestled in the woods like something out of a dream. We were very comfortable and had everything we needed. We actually had to stay two extra nights due to snow, which worked out fine. Alicia is an excellent host! "
The price is €192
includes taxes & fees
16 Mar - 17 Mar
Whimsical Creekside Cabin

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

10.0 out of 10, Exceptional, (309)
"Clean, cozy,and convenient!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

10.0 out of 10, Exceptional, (162)
"We loved being slopeside all weekend and enjoyed the amazing kitchen and amenities at the Dobie condo. Cannot say enough about how everything was just perfect for us! Many thanks for offering this lovely rental!"
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

10.0 out of 10, Exceptional, (32)
"We booked this property for a weekend break, and it was everything we hoped for and more! Pictures are accurate but can't possibly capture the impeccably designed and decorated house or the idyllic surroundings.The house was perfect for four adults, with a kitchen that rivals any we have seen. Everything, from the bed linens and bath towels to the kitchen supplies and wood fireplace, made our stay easy and special.We stayed on a rainy weekend, but the nearby Craft Beverage Trail (Nelson 151) was...
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

The newest and largest edition to the Wintergreen Retreat portfolio!

9.6 out of 10, Exceptional, (39)
"17 family members stayed for a long holiday weekend and this house was absolutely perfect! The open floor plan on the main floor offered something for everyone! The kitchen is spacious, has every amenity imaginable including two refrigerators. We used the two sided fireplace which kept us toasty and added to the ambiance. The guys loved having the pool table, and the comfy chairs by the window became the perfect spot to sip some wine and watch the snow fall. We loved the rustic mountain...
The newest and largest edition to the Wintergreen Retreat portfolio!

Mountaintop Wintergreen Resort House w/ Deck

9.8 out of 10, Exceptional, (12)
"We had a wonderful stay at this property and highly recommend it. We would definitely stay again. It was very clean, and the property manager was easy to work with. We were not sure about some of the layout in advance. Maybe this will help a future renter. Entering at the front door – areas are spacious. There are two large sitting areas on this level with a step down from the entry for one – two areas along with the dining and kitchen area circle and are open and spacious. The main level...
Mountaintop Wintergreen Resort House w/ Deck

Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

9.8 out of 10, Exceptional, (128)
"We had a family get together and everything was fantastic."
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

4 BR cabin mins to trails & breweries pets welcome

9.8 out of 10, Exceptional, (21)
"Excellent location, clean, comfortable, would stay again!"
The price is €653
includes taxes & fees
5 Mar - 6 Mar
4 BR cabin mins to trails & breweries pets welcome

Insane Mountain Views - New Listing

10.0 out of 10, Exceptional, (25)
"Our stay at this incredible mountain home in Wintergreen Resort was nothing short of spectacular! From the moment we arrived, we were blown away by the breathtaking views and the warm, welcoming atmosphere of the house. Every detail was thoughtfully designed to provide both comfort and luxury, making it the perfect setting for our long-overdue family reunion. With seven beautifully appointed bedrooms, each family had their own space while still enjoying the togetherness we were craving after a...
Insane Mountain Views - New Listing

Elegant & Modern Carriage House at Twin Maple Farm

10.0 out of 10, Exceptional, (187)
"Our second stay at the home, just as lovely."
The price is €181
includes taxes & fees
27 Feb - 28 Feb
Elegant & Modern Carriage House at Twin Maple Farm

The Modern Mountain Condo

10.0 out of 10, Exceptional, (21)
The price is €215
includes taxes & fees
5 Mar - 6 Mar
The Modern Mountain Condo

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

10.0 out of 10, Exceptional, (85)
"Had a great time. House was just as described. Spa was great. "
HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome
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

Wingate by Wyndham Waynesboro

2.5 star property
8.6 out of 10, Excellent, (782)
"It was a great stay! Room was clean and breakfast was very good. The staff were very kind and provided us with what we needed. "
The price is €77
includes taxes & fees
5 Mar - 6 Mar
Wingate by Wyndham Waynesboro

Sleep Inn Staunton

2.5 star property
9.2 out of 10, Wonderful, (1060)
"Clean friendly comfortable good breakfast "
The price is €89
includes taxes & fees
4 Mar - 5 Mar
Sleep Inn Staunton

Hotel 24 South

3.0 star property
9.4 out of 10, Exceptional, (1001)
"The property is beautiful, excellent location."
The price is €110
includes taxes & fees
2 Mar - 3 Mar
Hotel 24 South
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.

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 George Washington National Forest. 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.