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

House on the slopes Ski-in/out

9.4 out of 10, Exceptional, (41)
"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!

10.0 out of 10, Exceptional, (13)
"We had a wonderful time at the Harvest Moon. Good location for a mountain getaway. The house is decorated nicely and is cozy. Basement is a plus with the pool table, air hockey and hot tub. The owners were easy to reach and answered all my questions in a timely manner. I hope to go again one day!"
The price is AED 1,466
AED 2,735 total
includes taxes & fees
21 May - 22 May
Epic Mountain Views, Hot Tub and Privacy at Harvest Moon Lodge and Retreat!

Wintergreen Ridge Retreat

2.0 star property
9.4 out of 10, Exceptional, (3)
"This house was very spacious and well stocked. It was close to all of our activities. "
The price is AED 1,153
AED 2,331 total
includes taxes & fees
20 May - 21 May
Wintergreen Ridge Retreat

Hansel 'n Gretel: Wood Stove Grill Firepit Dogs OK

9.8 out of 10, Exceptional, (9)
"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."
Hansel 'n Gretel: Wood Stove Grill Firepit Dogs OK

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

10.0 out of 10, Exceptional, (3)
"We had a pleasant stay at the property. It was quiet and peaceful, exactly what we needed since we had a busy event scheduled."
Majestic Mtn Cabin w quick hiking access & short distance to overlook!

Elk Mountain Overlook: Breathtaking Views

2.0 out of 10, (1)
"The location and view (and privacy) were outstanding. The house is cute, easily accommodates 2 people (4 would be ok, but bathroom sharing amongst 4 could be a challenge), and has all of the amenneties to ensure maximimum comfort (blue tooth speaker, decently stocked kitchen, coffee and related items, cute decor, and plenty of towels and hot water."
Elk Mountain Overlook: Breathtaking Views

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

10.0 out of 10, Exceptional, (9)
"Just like the pictures, don't hesitate! Just book!!"
Opulent Retreat Amidst Blue Ridge's Serenity * Dog Friendly * Hot Tub

Luxury Chalet, Best Views in Virginia

9.8 out of 10, Exceptional, (28)
"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

10.0 out of 10, Exceptional, (3)
"My family and I recently spent a long weekend in August at this family-friendly chalet in Wintergreen and loved every moment. The owners really thought of everything! Highly recommend! "
Fam-Friendly Mountain Chalet: Hot Tub, Sauna, Gameroom, Adventure Bunkbeds

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

10.0 out of 10, Exceptional, (117)
"We had a fantastic stay! Location is great, very clean and comfortable. Would not hesitate to return! "
Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.

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

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

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
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

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (181)
"Liked the kitchen, but towels, hangers were not plentiful & had to ask at desk. Shower/tub needs safety grab bars. Shower curtain was impossibly long in shower & dangerous.. but "
The price is AED 368
AED 410 total
includes taxes & fees
25 May - 26 May
Valley Extended Suites

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

10.0 out of 10, Exceptional, (20)
"Love how we were surrounded by nature and the sound of the little river near us was so peaceful! Very clean and cozy."
The price is AED 533
AED 829 total
includes taxes & fees
19 May - 20 May
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

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

9.6 out of 10, Exceptional, (126)
"This property is one of the best prperties we have ever stayed at. The owner is very responsive and goes the extra mile. We will definitely rent this property again!!"
The price is AED 404
AED 907 total
includes taxes & fees
19 May - 20 May
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
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.