Photo by Brittany Davidson

Search and Rent Middlebrook Condos

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Condo Rentals 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, (289)
"The condo has just the right amenities, nicely decorated, and yes, a million dollar view."
$216 nightly
The price is $243
Aug 14 - Aug 15
Total includes taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Pool

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

9.6 out of 10, Exceptional, (130)
"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!!"
$219 nightly
The price is $246
Aug 13 - Aug 14
Total includes taxes and fees
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (323)
"I’ve stayed here a few times now with various members of my family and all of us love this place! The accommodations are great, the place is well stocked with careful attention to detail, and we always look forward to returning. Thanks again for a great stay!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Wintergreen. Sunset Vista Villa - Sea of Mountains
Interior

Wintergreen. Sunset Vista Villa - Sea of Mountains

10.0 out of 10, Exceptional, (76)
"Everything was great!"
$243 nightly
The price is $273
Aug 28 - Aug 29
Total includes taxes and fees
Wintergreen. Sunset Vista Villa - Sea of Mountains
Walk to Market/Private community outdoor pool!
Fridge, microwave, oven, stovetop

Walk to Market/Private community outdoor pool!

9.8 out of 10, Exceptional, (71)
"Excellent location. Comfortable and clean."
Walk to Market/Private community outdoor pool!
Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking
Smart TV, fireplace

Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking

10.0 out of 10, Exceptional, (2)
"Exterior of the building is a bit dated, but this unit has a fresh and updated feel to it. Everything we needed was provided. Quiet and very clean. Host was easy to work with. I'll definitely check to see if this unit is available the next time I'm visiting.Note: As mentioned in the description, there are a lot of steps to go down (and then back up)."
Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking
Mountain View Vista: Resort Condo w/ Views
TV, fireplace

Mountain View Vista: Resort Condo w/ Views

10.0 out of 10, Exceptional, (4)
"Beautiful view!"
$259 nightly
The price is $291
Aug 14 - Aug 15
Total includes taxes and fees
Mountain View Vista: Resort Condo w/ Views
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall
Property grounds

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

9.8 out of 10, Exceptional, (48)
"Great place, easy to find, and quick drive to the Wontergreen Resort!"
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
Exterior

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

9.8 out of 10, Exceptional, (50)
"Had a great stay! Easy check-in/departure process. Great views and easy access to the slopes! 10/10 would recommend again. "
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
Time to Book for Spring and Summer...Amazing Views and 5-Star Amenities
Outdoor dining

Time to Book for Spring and Summer...Amazing Views and 5-Star Amenities

10.0 out of 10, Exceptional, (299)
"Amazing stay with everything g we needed. It would be nice to have access to a pool. "
Time to Book for Spring and Summer...Amazing Views and 5-Star Amenities
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
A heated pool

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

9.8 out of 10, Exceptional, (130)
"Great ski-in / ski-out."
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
Ski-In/Ski-Out Comfy Condo
Fridge, microwave, oven, stovetop

Ski-In/Ski-Out Comfy Condo

10.0 out of 10, Exceptional, (24)
"Great place with ski-in ski-out access! Well appointed and photos are accurate. Host was great! We would definitely stay again. "
Ski-In/Ski-Out Comfy Condo
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
Interior

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

10.0 out of 10, Exceptional, (71)
"What a beautiful view and location! We appreciated the details Della shared prior to our arrival and made navigating our weekend getaway super simple and enjoyable! Beautiful view! "
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
New! Downtown Loft - Walk to WLU & VMI
Fridge, microwave, oven, stovetop

New! Downtown Loft - Walk to WLU & VMI

10.0 out of 10, Exceptional, (9)
"This apartment was conveniently located in downtown Lexington, Virginia. It was extremely clean and had very nice accommodations. I will definitely stay there again in the future."
$405 nightly
The price is $431
Aug 20 - Aug 21
Total includes taxes and fees
New! Downtown Loft - Walk to WLU & VMI
Laptop-Friendly Lexington Condo w/ Free WiFi
Exterior

Laptop-Friendly Lexington Condo w/ Free WiFi

9.4 out of 10, Exceptional, (13)
"Clean, comfortable and had all the essentials"
Laptop-Friendly Lexington Condo w/ Free WiFi
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
Smart TV, fireplace, books

Stylish-Updated-Central -Walk to Slopes-Dogs OK!

9.8 out of 10, Exceptional, (20)
"Clean, convenient to everything. Great place!"
$211 nightly
The price is $237
Aug 14 - Aug 15
Total includes taxes and fees
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
Panoramic Peak: Wintergreen Condo with Views
TV, fireplace

Panoramic Peak: Wintergreen Condo with Views

9.6 out of 10, Exceptional, (26)
"With its breathtaking views, this property is a hidden gem. It is also very well maintained. "
$259 nightly
The price is $291
Aug 13 - Aug 14
Total includes taxes and fees
Panoramic Peak: Wintergreen Condo with Views
Prime Spring Retreat: Walk, Sip, Hike, Relax, Explore at Dobie Slopeside
Pool

Prime Spring Retreat: Walk, Sip, Hike, Relax, Explore at Dobie Slopeside

10.0 out of 10, Exceptional, (16)
"Our stay was fantastic. All the little details made the stay even better. Hand soap, bathroom and kitchen supplies, extra blankets. Beds were very comfortable too! Will definitely stay here again. "
Prime Spring Retreat: Walk, Sip, Hike, Relax, Explore at Dobie Slopeside
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Fridge, microwave, oven, stovetop

Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

9.6 out of 10, Exceptional, (44)
"We took our two kids and our poodle, Rocky, for a few days of hiking and unplugging! It was the perfect spot!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Wintergreen Condo -Steps to Ski and restaurants
Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

9.8 out of 10, Exceptional, (22)
"My brother and his friend stayed here to go snow skiing and loved it "
$234 nightly
The price is $263
Aug 20 - Aug 21
Total includes taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlebrook Hotel Reviews

Wingate by Wyndham Lexington

Wingate by Wyndham Lexington

10/10 Excellent
"Breakfast was part of the overnight stays. The coffee was good, but the food was underwhelming. Not a large selection of anything. More fresh fruit, some fresh pastries or muffins would have been appreciated. "
Anonymous traveler 1-night trip
Posted 1 day ago
Wingate by Wyndham Lexington