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

Next weekend
In two weeks
In one month
In two months

Compare 288 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, (291)
"Fun, fun times in a short stay. Location was perfect ! "
The price is AED 555
AED 1,415 total
includes taxes & fees
19 Feb - 20 Feb
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, (46)
"Great ski in ski out house at Wintergreen. Our family had a blast skiing and hanging at this great house. We enjoyed games, hot tub, great kitchen for cooking in. Danessa was extremely hospitable and commmnicated with us very well! Highly recommend. "
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)
"The house is perfect and only 10 minutes from the slopes."
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, (189)
"Another mom and I spent two nights in the Alone Mill Schoolhouse while our sons enjoyed a weekend tour of VMI. The house was close to campus and offered all the conveniences we needed. The setting was beautiful! I wish we would have had more time to enjoy our surroundings! Maybe we will stay here again if our boys become cadets!"
Alone Mill Schoolhouse - A paradise for outdoor lovers

Hilltop Escape At Wintergreen

2.0 star property
8.8 out of 10, Excellent, (3)
"This is not a 5-bedroom home. This is a 4-bedroom home with a less than double bed futon in the main living space with no door or separation; this was a problem for our family. The home overall is very nice with comfortable beds and pleasant gathering space. "
Hilltop Escape At Wintergreen

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

9.4 out of 10, Exceptional, (81)
"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, (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!

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 AED 1,466
AED 3,482 total
includes taxes & fees
10 Feb - 11 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 AED 577
AED 1,101 total
includes taxes & fees
11 Feb - 12 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, (129)
"Really ideally located in downtown Lexington "
Restored 1840 House with Gardens in Historic Downtown

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

8.0 out of 10, Very Good, (1)
"The property was gorgeous and just as described. The views were absolutely beautiful. The hot tub didn’t looked to have been serviced recently but really the only negative was the stairs. The stairs from the driveway to the front door had tons of leaves daily, a leaf blower would have been great. The lighting at the top of the stairs didn’t work at all, it is very dangerous at night. Overall it was a great property and ideal for peak fall foliage week! "
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, (12)
"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

9.8 out of 10, Exceptional, (13)
"Great communication with host. Spotless. Well done renovation with modern amenities. "
The price is AED 511
AED 1,267 total
includes taxes & fees
10 Feb - 11 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, (263)
"We really appreciate the cleanliness and location of this property! We had a great stay and look forward to returning! Ps love the art!! "
The price is AED 386
AED 895 total
includes taxes & fees
11 Feb - 12 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 AED 674
AED 977 total
includes taxes & fees
10 Feb - 11 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, (291)
"Fun, fun times in a short stay. Location was perfect ! "
The price is AED 555
AED 1,415 total
includes taxes & fees
19 Feb - 20 Feb
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.