Photo by Brittany Davidson

Search Vacation Homes in Middlebrook

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 286 Vacation Homes in Middlebrook with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (294)
"Cozy, Clean and Convenient!"
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

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

10.0 out of 10, Exceptional, (49)
"We had a great family ski trip with the convenience of the cabin. After skiing it is nice to come back to a warm, comfy cabin that has nice kitchen, warm fireplaces and hot tub to relax. We would highly recommend! "
The price is SAR 1,500
SAR 2,687 total
includes taxes & fees
2 Mar - 3 Mar
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

10.0 out of 10, Exceptional, (63)
"We thoroughly enjoyed our stay in this quiet home in the woods. It is an ideal size for 2 couples or a small family. The layout makes it perfect for visiting and it has everything you need. The host responded immediately to any questions and check in was a breeze. It is just a short drive to the outdoor pool and there are incredible trails throughout Wintergreen. Lovely decks (upper and lower) are surrounded by trees and a forest of ferns. The beds are very comfortable. Overall we had a lovely...
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

Wintergreen Resort Post & Beam Home Beauty

9.8 out of 10, Exceptional, (16)
"Everything about the listing and the location was spot on. We have stayed in numerous VRBO-units all over, and this was one of the most well-stocked homes I’ve seen. The house was very convenient to Wintergreen for fun winter activities, and the three bedrooms bathrooms were perfect for our family of 5. The kids loved the little loft space for playing card games, and we loved the view from the main living room. The only thing I’d suggest to the owner would be a handy-man to tighten the...
Wintergreen Resort Post & Beam Home Beauty

Alone Mill Schoolhouse - A paradise for outdoor lovers

9.6 out of 10, Exceptional, (190)
"Very fun getaway property. Well equipped kitchen, comfy beds, coffee makers and well heated/insulated in the wintry weather. Property is lovely for walks and must be amazing in all seasons. Close enough to Lexington for errands, far enough away to be secluded and quiet. Pool Table was a big hit!"
Alone Mill Schoolhouse - A paradise for outdoor lovers

Hilltop Escape At Wintergreen

2.0 star property
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our time in the house! We loved the family room and fireplace. The kitchen was also very well stocked. We appreciated so much all the extra amenities of soap, shampoo and body wash. As well as firewood for the fireplace. The hot tub was broken… but the property manager was exceptional! He tried his best to get it up and running but was unsuccessful. He was very responsive and kind. "
Hilltop Escape At Wintergreen

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

9.4 out of 10, Exceptional, (82)
"Beautiful area and beautiful home."
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, (173)
"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!

Cooler in the mountains, with hot tub.

9.8 out of 10, Exceptional, (65)
"House was perfect for a weekend of skiing. You’re able to walk to the resort from the house which was a huge plus since it was a packed weekend. Overall great stay! "
Cooler in the mountains, with hot tub.

Red White & WTG: Game Room + Hot Tub

The price is SAR 1,346
SAR 3,411 total
includes taxes & fees
25 Feb - 26 Feb
Red White & WTG: Game Room + Hot Tub

3 BR house with hot tub near Lexington and surrounding attractions!

9.8 out of 10, Exceptional, (42)
"The place is really nice with a Jacuzzi, large covered patio, comfortable beds with fans! However, I had trouble finding and accessing messages from the owner that she sent through VRBO. All previous hosts had communicated directly with me via text or emails (which is simple and reliable). I called VRBO service when I got no text or emails from this owner, and they sent me a text stating how to get into the house, but no more info. Via text, she told me that the detailed info for guests was...
The price is SAR 589
SAR 1,124 total
includes taxes & fees
25 Feb - 26 Feb
3 BR house with hot tub near Lexington and surrounding attractions!

Restored 1840 House with Gardens in Historic Downtown

9.8 out of 10, Exceptional, (130)
"We enjoyed a wonderful return to the Lexington area made perfect with this lovely home. Excellent Location. Spacious. Clean. Spacious. We hope to return again someday!"
Restored 1840 House with Gardens in Historic Downtown

4min to Ski! Mntn Views Hot Tub Fireplace 52" Roku

9.4 out of 10, Exceptional, (3)
"The property was well stocked and the location was excellent. There was plenty of firewood for the fireplace and the hot tub was perfect after a long day of skiing at the resort. "
4min to Ski! Mntn Views Hot Tub Fireplace 52" Roku

Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

10.0 out of 10, Exceptional, (42)
"Everything was as advertised- family of 6 was well accommodated for a Thanksgiving weekend. Very cold windy and snowy outside but house was warm and comfortable. Very large kitchen was well suited for preparing Thanksgiving dinner. "
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

Secluded winter getaway, Nelson 151, MTN views!

10.0 out of 10, Exceptional, (13)
"Great stay. I only wish the 2 days of rain had been snow!"
Secluded winter getaway, Nelson 151, MTN views!

3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

10.0 out of 10, Exceptional, (55)
"This was the prefect house for the holiday. Plenty of space for our family yet very cozy. The temps were cold and we had the fire place going every night. The views from the main room and master suite were breathtaking. The owners were very responsive and communicative. Highly recommend this home to anyone wanting a mountain getaway to Wintergreen resort!"
3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

White Rock Cabin

10.0 out of 10, Exceptional, (199)
"Above and beyond on everything highly recommend staying here"
White Rock Cabin

Cozy Craftsman: Newly Renovated/Downtown Staunton

9.6 out of 10, Exceptional, (15)
"We had a wonderful stay at the Cozy Craftsman! The home is beautiful and clean, great kitchen, two full bathrooms, and lots of space. It is super close to downtown (15 minute walk or a few minutes drive). We would definitely stay here again and would recommend to everyone!"
The price is SAR 521
SAR 1,311 total
includes taxes & fees
24 Feb - 25 Feb
Cozy Craftsman: Newly Renovated/Downtown Staunton

Historic House with Gardens Near Universities & Downtown

9.4 out of 10, Exceptional, (49)
"Great place will stay there again. Need to book it "
Historic House with Gardens Near Universities & Downtown

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
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.
Don't see what you're looking for?
See all available properties in Middlebrook
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Middlebrook

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

9.0 out of 10, Wonderful, (265)
"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 SAR 394
SAR 914 total
includes taxes & fees
24 Feb - 25 Feb
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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 SAR 406
SAR 452 total
includes taxes & fees
26 Mar - 27 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)
"Cozy, Clean and Convenient!"
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
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.