Photo by Brittany Davidson

Middlebrook Holiday Rentals

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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, (261)
"Love this place. Amazing views and very spacious. The wood burning fireplace was nice bonus!! Would love to return. "
The price is AU$393
includes taxes & fees
3 Feb - 4 Feb
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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 AU$435
includes taxes & fees
3 Feb - 4 Feb
Love Ridge Mountain Lodging

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

9.6 out of 10, Exceptional, (289)
"Amazing little getaway, private, quiet and everything you need right there. "
The price is AU$621
includes taxes & fees
12 Feb - 13 Feb
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (173)
"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$180
includes taxes & fees
3 Feb - 4 Feb
Valley Extended Suites

View from the Top

10.0 out of 10, Exceptional, (51)
"Great quick stay in a lovely area with an amazing view"
View from the Top

The Modern Mountain Condo

10.0 out of 10, Exceptional, (19)
"We had a great stay, the place is a good size for four friends, and the couch bed is super comfortable. Easy walk to skiing, convenient check in, and those host was communicative. "
The price is AU$356
includes taxes & fees
11 Feb - 12 Feb
The Modern Mountain Condo

Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

10.0 out of 10, Exceptional, (43)
"Place was as described right off the slopes. Great communication with property manager."
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

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

10.0 out of 10, Exceptional, (303)
"This was an amaizng VRBO. Heather was very responsive and accommodating. The codo itself is perfect for a family, or if you are a couple. As a family my kids, 8, 4 and 2 e joted the playroom nook with the Wii and the queen and twin beds. The views were spectacular. We arrived im the middle of Winter Storm Blair and got about a foot of snow dumped on us so the wood burning fireplace and board games were a hit as night creeped in. We are very thankful for heather and her VRBO and highly recommend....
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (58)
"The property was great and exactly as advertised. I’ve stayed at four places around Wintergreen, and this was definitely the best. The communication and responsiveness from the hosts was perfect."
The price is AU$656
includes taxes & fees
18 Feb - 19 Feb
Endless Mountain Top Views from All The Way Up!

Luxury cabin in the woods, 2 bedrooms plus loft

10.0 out of 10, Exceptional, (158)
"Excellent cabin with a lot of space to stretch out, very private and well-appointed. A great place to escape for a few days. Wonderful hosts! "
Luxury cabin in the woods, 2 bedrooms plus loft

Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

10.0 out of 10, Exceptional, (62)
"The house is perfect and only 10 minutes from the slopes."
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

9.4 out of 10, Exceptional, (80)
"We had a great time. House was lovely and had everything we needed. The living area was spacious and accommodated large family gatherings for dinner and relaxing. The young adults liked the proximity to the slopes for snowboarding. We would definitely stay again. "
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

9.8 out of 10, Exceptional, (172)
"Excellent stay overall. Weather kept us from enjoying the outside much but the cozy fireplace inside was super nice, especially with the supplied wood. Furniture was comfy and the smart TVs and streaming/cable was fabulous! "
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

Wintergreen Resort Post & Beam Home Beauty

9.6 out of 10, Exceptional, (15)
"Our pre-Thanksgiving in the mountains could not have been more perfect. This home was lovely, comfortable, and well-appointed in every way. We had a one-year-old plus 3 couples and loved that we all had privacy, separate bathrooms, and a cozy family space. I highly recommend this home for your next mountain getaway!"
Wintergreen Resort Post & Beam Home Beauty

The newest and largest edition to the Wintergreen Retreat portfolio!

9.6 out of 10, Exceptional, (38)
"Loved staying here…felt like home away from home! Nathan was super helpful and friendly. He even put up a Christmas tree for us. Fantastic stay! "
The newest and largest edition to the Wintergreen Retreat portfolio!

Ski-In/Ski-Out Comfy Condo

10.0 out of 10, Exceptional, (20)
"The condo was clean, cute and well stocked. The ski out location was just perfect for our ski trip to wintergreen "
Ski-In/Ski-Out Comfy Condo

Panoramic Peak: Wintergreen Condo with Views

9.6 out of 10, Exceptional, (20)
"Very nice condo with great views."
The price is AU$487
includes taxes & fees
4 Feb - 5 Feb
Panoramic Peak: Wintergreen Condo with Views

Relaxing Wintergreen Chalet

8.0 out of 10, Very good, (21)
"Our stay was great. I think, It’s located within the wintergreen resort properties. so it’s secluded yet lots of cabins around to make you feel safe. The house itself is well stocked with kitchen gadgets, from basics like coffee maker to air fryer, grinder etc. All the bedrooms are in the lower floor and they could use some updates. The bedrooms had a musty smell when entering. But there are air purifiers in the room, which was helpful to remove the smell. Apart from that we had a great stay....
Relaxing Wintergreen Chalet

Wintergreen Resort Vacation Rental w/ Pool Access!

10.0 out of 10, Exceptional, (13)
"The place was clean and cozy. The master bedroom mattress is very firm (arm kept falling asleep) and the unit is a bit drafty. Short drive to the slopes and walkable to the clubhouse\pool. Overall, I would stay again."
Wintergreen Resort Vacation Rental w/ Pool Access!

Wintergreen Condo w/ Balcony + Mountain Views!

9.8 out of 10, Exceptional, (28)
"Great views of the mountains. Beautiful place."
Wintergreen Condo w/ Balcony + Mountain Views!
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

Motel 6 Staunton, VA

2.0 star property
8.2 out of 10, Very good, (1004)
"Great place to stay!!!"
The price is AU$103
includes taxes & fees
6 Feb - 7 Feb
Motel 6 Staunton, VA

Wingate by Wyndham Waynesboro

2.5 star property
8.6 out of 10, Excellent, (766)
"Stayed here with my boys for a quick one night and it was great. The pool was great, water was warm and area was clean. Room was clean and comfortable. Staff was pleasant."
The price is AU$123
includes taxes & fees
9 Feb - 10 Feb
Wingate by Wyndham Waynesboro

Hotel 24 South

3.0 star property
9.4 out of 10, Exceptional, (1009)
"Very nice hotel in a great location."
The price is AU$190
includes taxes & fees
28 Feb - 1 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.