Middlebrook, VA Chalets from SAR 653

Check prices for these dates

Next weekend

28 Rab. I - 30 Rab. I

In two weeks

4 Rab. II - 6 Rab. II

In one month

18 Rab. II - 20 Rab. II

In two months

16 Jum. I - 18 Jum. I

Compare 14 Chalets in Middlebrook with updated reviews, rates, and availability.

"We’ve stayed in over a dozen rentals in the area throughout the last few years and this property was without a doubt one of our favorites. Very clean, has everything you could need and more. Waking up every morning and walking out into the living room to the most beautiful and unreal views of the blue ridge mountains was the highlight of the trip! "

SAR 4,364 total

includes taxes & fees

20 Apr - 21 Apr

"We had a great two day stay at the cabin with our family and friends! The property was clean, had ample sleeping space and in a great location-5 min drive to Wintergreen Resort. The host was responsive when we had questions during the stay and even beforehand. Would recommend for those with families! "

"We all loved the home. We were so comfortable and enjoyed all of the upgrades throughout the house. It was perfect for our gathering, and we hated to leave. The host was remarkably responsive, and went out of his way to ensure that we had a pleasant stay."

"Quiet neighborhood with a heavenly view. It snowed while we were there, and the area roads management was impressive.Property is reasonably well-appointed. Perhaps geared more toward an adult party venue, we did find family-oriented supplies limited. Bring your own games, books. I would not recommend this property for families with young children for obvious reasons. The price of the view is a higher risk of slip/falls on the back incline, especially in snow.This rental is a special blessing...

"I loved this place! There was plenty of space for family and the cabin was beautiful! We enjoyed the porch and firepit and the fireplace inside. The cabin was easy to find. I would stay here again."

"Chris was a wonderful host. The house is clean and very well proportioned. Our kids had a blast playing games and enjoying the other amenities. "

"We stayed with another family, 8 people total. The layout of the house was perfect and very accommodating for 4 teenagers. The house was clean. The kitchen was well stocked. The beds were very comfortable. We all enjoyed the hot tub. Holly was very kind and quick to respond to my messages. The only thing that was a little confusing, was the place was advertised as “ski in/ski out”. We did not ever see where that was possible? The house was not close enough to the slope to be considered ski...

SAR 1,711 total

includes taxes & fees

31 Mar - 1 Apr

"The cabin is exactly as pictured- it is beautiful, spacious yet cozy, and very clean. The host was attentive and pleasant. Three generations were in the house and all were very pleased. We thoroughly enjoyed our stay!"

"The communication was excellent before and during the stay - they checked in and followed up with us. The property had everything we needed for a great weekend. A quick 2 minute drive to the Wintergreen restaurants and small store. "

"The location was great for a ski vacation - an easy walk to the main lodge even with kids.The property itself is dated and could use a number of upgrades. Very basic amenities and light blankets on the beds - would definitely recommend bringing extra blankets (and towels) if you plan to stay for a cold weekend. The listing noted that there is access to an indoor pool which we found out was not the case and the property does not have resort access. "

"We live locally but had friends and family coming to town for my birthday so we rented Riley’s retreat. Our weekend was filled with visits to all the food and beverages on 151. I loved the fun amenities at the house ( hot tub, pool table, games, etc). My initial investigation I didn’t realize we we so far up Wintergreen but in the end it did not matter and was a perfect house for the weekend ! Thank you !!"

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Other property types in Middlebrook

"The date of my stay was Sun Feb 9 - Tues Feb 11, 2025. It was a great place to stay with beautiful views. Our stay was short. We were there for my son to participate in WASI- Wintergreen Alpine Special Invitational. Travel to the Mountain Inn for ski competition and celebration was easy. I really enjoyed having the full kitchen so we could make breakfast each day. The washer and dryer were helpful for keeping ski bibs clean and dry."

SAR 910 total

includes taxes & fees

23 Mar - 24 Mar

Standard Suite | Private kitchen | Full-size fridge, microwave, oven, stovetop

"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)"

SAR 447 total

includes taxes & fees

2 Apr - 3 Apr

2 bedrooms, iron/ironing board, travel crib, free WiFi

"We had such a nice getaway weekend at The Chestnut House. The Heiston’s went above and beyond to make our stay exceptional. The house was beautiful, cozy, and quiet. While sitting outside, the only thing we could hear was the relaxing sound of the river running through the backyard. The hosts made us feel very welcome and made it a wonderful experience. We would definitely book this home again. 10/10 recommend!"

Recent reviews of Middlebrook hotels

5/5 Excellent

Highly recommend.

"Great experience, everything about my stay was great. "

A verified traveler stayed at Hotel 24 South

Posted 2 days ago

Holiday Inn Staunton Conference Center by IHG

5/5 Excellent

Awesome Hotel

"Great hotel! Very large and clean. Staff is super friendly. They have a restaurant and bar, which we did not partake of. Breakfast is not free. Not sure what the restaurant serves or how much it costs as there is no menu anywhere. Rooms are spacious and clean. No problems at all. The hotel also has an indoor pool although it wasn't warm in the room when we visited. It is connected to the bar. There is also an outdoor pool. There are three conference rooms which can be joined for a presidential ballroom. We couldn't see inside since the doors were locked. Prob the best hotel we stayed at during our travels."

A verified traveler stayed at Holiday Inn Staunton Conference Center by IHG

Posted 2 days ago

Search Chalets in Middlebrook

Plan, book, stay with confidence

Check prices for these dates

Compare 14 Chalets in Middlebrook with updated reviews, rates, and availability.

Epic Mountain Views, Hot Tub and Privacy at Harvest Moon Lodge and Retreat!

Majestic Mtn Cabin w/ quick hiking acess & short distance to overlook!

Elk Mountain Overlook: Breathtaking Views

Opulent Retreat Amidst Blue Ridge's Serenity * Dog Friendly * Hot Tub

Luxury Chalet, Best Views in Virginia

2min to Ski! DogsOK Wood Stove Grill Fire Pit Hike

Fam-Friendly Mountain Chalet: Hot Tub, Sauna, Gameroom, Adventure Bunkbeds

Wintergreen Ridge Retreat

Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.

Hot Tub EV Charger Golden Tee Gig WiFi Pool Tennis

Sleepy Bear Chalet

Hot Tub EV Charger Golden Tee Gig WiFi Pool Tennis

A charming 2-bedroom chalet with outstanding view in the Shenandoah Valley.

Other property types in Middlebrook

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

Valley Extended Suites

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

Recent reviews of Middlebrook hotels

Hotel 24 South

Holiday Inn Staunton Conference Center by IHG

Holiday Inn Express And Suites Staunton by IHG

Holiday Inn Express And Suites Waynesboro East by IHG

Best Western Plus Inn at Hunt Ridge

The Blackburn Inn and Conference Center

Clarion Pointe Staunton East

Hampton Inn Lexington-Historic District

Sleep Inn Staunton

Explore a world of travel with Expedia

Popular Destinations

More Accommodation Types in Middlebrook