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Check prices for these dates

Next weekend
21 Rab. I - 23 Rab. I
In two weeks
28 Rab. I - 30 Rab. I
In one month
11 Rab. II - 13 Rab. II
In two months
9 Jum. I - 11 Jum. I

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

House on the slopes Ski-in/out
Fridge, microwave, oven, stovetop

House on the slopes Ski-in/out

9.6 out of 10, Exceptional, (39)
"Great location for a quick weekend getaway. Amenities were a plus and great access to Wintergreen resort. "
House on the slopes Ski-in/out
Epic Mountain Views, Hot Tub and Privacy at Harvest Moon Lodge and Retreat!
Outdoor spa tub

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

10.0 out of 10, Exceptional, (12)
"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! "
The price is SAR 1,496
SAR 2,801 total
includes taxes & fees
20 Mar - 21 Mar
Epic Mountain Views, Hot Tub and Privacy at Harvest Moon Lodge and Retreat!
Majestic Mtn Cabin w/ quick hiking acess & short distance to overlook!
Smart TV, fireplace, books

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

10.0 out of 10, Exceptional, (2)
"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! "
Majestic Mtn Cabin w/ quick hiking acess & short distance to overlook!
Elk Mountain Overlook: Breathtaking Views
Fireplace

Elk Mountain Overlook: Breathtaking Views

2.0 out of 10, (1)
Elk Mountain Overlook: Breathtaking Views
Opulent Retreat Amidst Blue Ridge's Serenity * Dog Friendly * Hot Tub
Aerial view

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

10.0 out of 10, Exceptional, (9)
"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."
Opulent Retreat Amidst Blue Ridge's Serenity * Dog Friendly * Hot Tub
Luxury Chalet, Best Views in Virginia
Outdoor spa tub

Luxury Chalet, Best Views in Virginia

9.8 out of 10, Exceptional, (27)
"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...
Luxury Chalet, Best Views in Virginia
Fam-Friendly Mountain Chalet: Hot Tub, Sauna, Gameroom, Adventure Bunkbeds
Outdoor dining

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

10.0 out of 10, Exceptional, (3)
"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. "
Fam-Friendly Mountain Chalet: Hot Tub, Sauna, Gameroom, Adventure Bunkbeds
2min to Ski! DogsOK Wood Stove Grill Fire Pit Hike
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (7)
"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."
2min to Ski! DogsOK Wood Stove Grill Fire Pit Hike
Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.
Interior

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

10.0 out of 10, Exceptional, (117)
"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!"
Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.
Wintergreen Ridge Retreat
Exterior

Wintergreen Ridge Retreat

2.0 star property
7.6 out of 10, Good, (4)
"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...
The price is SAR 653
SAR 1,710 total
includes taxes & fees
31 Mar - 1 Apr
Wintergreen Ridge Retreat
Hot Tub EV Charger Golden Tee Gig WiFi Pool Tennis
Exterior

Hot Tub EV Charger Golden Tee Gig WiFi Pool Tennis

10.0 out of 10, Exceptional, (3)
"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. "
Hot Tub EV Charger Golden Tee Gig WiFi Pool Tennis
Sleepy Bear Chalet
Property grounds

Sleepy Bear Chalet

8.0 out of 10, Very Good, (3)
"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. "
Sleepy Bear Chalet
Hot Tub EV Charger Golden Tee Gig WiFi Pool Tennis
Exterior

Hot Tub EV Charger Golden Tee Gig WiFi Pool Tennis

9.4 out of 10, Exceptional, (3)
"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 !!"
Hot Tub EV Charger Golden Tee Gig WiFi Pool Tennis
A charming 2-bedroom chalet with outstanding view in the Shenandoah Valley.
View from property

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

2.0 star property
A charming 2-bedroom chalet with outstanding view in the Shenandoah Valley.
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 property types in Middlebrook

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

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

9.0 out of 10, Wonderful, (267)
"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."
The price is SAR 394
SAR 906 total
includes taxes & fees
18 Mar - 19 Mar
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Valley Extended Suites
Standard Suite | Private kitchen | Full-size fridge, microwave, oven, stovetop

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 SAR 406
SAR 452 total
includes taxes & fees
24 Mar - 25 Mar
Valley Extended Suites
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
2 bedrooms, iron/ironing board, travel crib, free WiFi

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

10.0 out of 10, Exceptional, (35)
"We could not have had a more wonderfully refreshing stay in this beautiful spot on the Piney River in the charming Chestnut House. Maria’s thoughtfulness as a host cannot be understated. The home is supplied with every need and comfort. We slept soundly, enjoyed the fire pit, fishing, naps in the hammock, coffee in the front porch rockers, reading on the deck by the river, hikes from the house, and cooking in the beautifully stocked kitchen. We cannot wait to return! "
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
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.