Photo by Brittany Davidson

Search Condo Rentals 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 305 Condo Rentals in Middlebrook with updated reviews, rates, and availability.

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, (271)
"Overall it was great. Location is stunning and perfect for our hiking plans. Kitchen equipment needs to be replaced so if you plan to cook bring your own. "
The price is SAR 360
SAR 851 total
includes taxes & fees
17 Apr - 18 Apr
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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

10.0 out of 10, Exceptional, (312)
"Great stay, highly recommended"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
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, (124)
"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 SAR 413
SAR 906 total
includes taxes & fees
30 Apr - 1 May
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
Interior

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

10.0 out of 10, Exceptional, (61)
"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
Wintergreen Condo -Steps to Ski and restaurants
Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

10.0 out of 10, Exceptional, (15)
"Cozy and clean. Fire place was lovely. Would return again! Thank you!"
The price is SAR 356
SAR 885 total
includes taxes & fees
21 Apr - 22 Apr
Wintergreen Condo -Steps to Ski and restaurants
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️
Property grounds

Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

10.0 out of 10, Exceptional, (169)
"We've wanted to stay in the Dobies for a while now. We have been in most every property from Eagles Court to the Cliffs to the Timbers and Diamond Hill. Location is perfect. This unit is clean and well kept. It has a great view at sunrise and entertaining view all day watching the lift. So convenient to ski lessons and food for our children. Couldn't have had a better time. The PM is awesome! Great customer service skills. Highly recommend this place. It was so great we booked it...
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️
Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
Smart TV, fireplace, books

Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo

10.0 out of 10, Exceptional, (4)
"We loved the condo, great location, overlooking slopes, parking ri"
Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
Endless Mountain Top Views from All The Way Up!
Property grounds

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (70)
"Lovely place with beautiful views!"
Endless Mountain Top Views from All The Way Up!
View from the Top
Smart TV, fireplace, DVD player, books

View from the Top

10.0 out of 10, Exceptional, (54)
"Clean and convenient"
View from the Top
Wintergreen. Minutes from ski slopes Sunset Vista Villa - Sea of Mountains
Interior

Wintergreen. Minutes from ski slopes Sunset Vista Villa - Sea of Mountains

10.0 out of 10, Exceptional, (66)
"We really enjoyed staying here! The location was great and perfect for a long weekend. "
The price is SAR 488
SAR 1,041 total
includes taxes & fees
21 Apr - 22 Apr
Wintergreen. Minutes from ski slopes Sunset Vista Villa - Sea of Mountains
Downtown Loft - King Beds - Walk to WLU & VMI!
Fridge, microwave, oven, stovetop

Downtown Loft - King Beds - Walk to WLU & VMI!

9.8 out of 10, Exceptional, (7)
"Great space! Plenty of room. Clean and comfortable. Had everything you could need.Thank you! "
The price is SAR 814
SAR 1,806 total
includes taxes & fees
12 May - 13 May
Downtown Loft - King Beds - Walk to WLU & VMI!
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Outdoor dining

Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

9.6 out of 10, Exceptional, (26)
"We loved this condo. It was in the perfect location for our stay at Wintergreen. We could walk to the resort. Very well stocked with everything you need! We will book this place again!"
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Walk to Market/Private community outdoor pool!
Fridge, microwave, oven, stovetop

Walk to Market/Private community outdoor pool!

9.6 out of 10, Exceptional, (67)
"Condo was great. Easy walk to slopes and I am old. I would stay again. One issue, hot water only good for 1 shower. I think there is issue with hot water heater as it is big enough. 1 shower and water was cold. Otherwise great stay."
Walk to Market/Private community outdoor pool!
Walk to Lifts: Wintergreen Resort Condo
Exterior

Walk to Lifts: Wintergreen Resort Condo

7.6 out of 10, Good, (5)
"We love being close to the Market and the slopes. The property was clean, comfortable and perfect for our weekend trip! "
Walk to Lifts: Wintergreen Resort Condo
Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views
Miscellaneous

Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views

9.8 out of 10, Exceptional, (46)
"I was really disappointed with the hidden giant deposit charge when I booked the rental. We did not get it refunded until weeks after staying at the property."
Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views
Wintergreen Resort Vacation Rental w/ Pool Access!
Property grounds

Wintergreen Resort Vacation Rental w/ Pool Access!

10.0 out of 10, Exceptional, (16)
"Nice place, as described. Easy checkin and out. "
Wintergreen Resort Vacation Rental w/ Pool Access!
Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.
Property grounds

Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

10.0 out of 10, Exceptional, (141)
"Wonderful experience close to all of the action at Wintergreen. Everything you need is in the condo and the 2 min walk to the market is super convenient! Will come again for sure."
Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.
Mountain Dreams Condo with Aspen Suite & 2 Floors
TV, fireplace, books

Mountain Dreams Condo with Aspen Suite & 2 Floors

10.0 out of 10, Exceptional, (65)
"The perfect spot for an excellent ski weekend. Condo has incredible views of the slopes and mountains. Perfect layout for families. Well stocked with everything we needed. Walking across the street for some great pizza or an easy walk/drive to the lodge. "
The price is SAR 574
SAR 1,477 total
includes taxes & fees
21 Apr - 22 Apr
Mountain Dreams Condo with Aspen Suite & 2 Floors
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Miscellaneous

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

9.4 out of 10, Exceptional, (10)
"Everything was wonderful! My only complaint is that I wish check out was later, because it was so peaceful and relaxing. The little touches were great, and we had an excellent stay! If we’re in need of a place to stay in the area again without the kids, we will definitely be back. "
The price is SAR 371
SAR 822 total
includes taxes & fees
21 Apr - 22 Apr
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Ski-In Ski-Out Wintergreen Condo w/ Balcony
Interior

Ski-In Ski-Out Wintergreen Condo w/ Balcony

9.6 out of 10, Exceptional, (42)
"Would stay here again"
Ski-In Ski-Out Wintergreen Condo w/ Balcony
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
Sign in
Sign up, it's free

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, (271)
"Overall it was great. Location is stunning and perfect for our hiking plans. Kitchen equipment needs to be replaced so if you plan to cook bring your own. "
The price is SAR 360
SAR 851 total
includes taxes & fees
17 Apr - 18 Apr
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, (177)
"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 355
SAR 395 total
includes taxes & fees
21 Apr - 22 Apr
Valley Extended Suites
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
Exterior

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

10.0 out of 10, Exceptional, (40)
"The cabin was incredibly cozy and a complete joy to stay in. What an incredibly historical place"
The price is SAR 518
SAR 894 total
includes taxes & fees
24 Apr - 25 Apr
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
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.

Frequently asked questions

Why book your condo in Middlebrook with Expedia?
Use Expedia to find your ideal condo in Middlebrook. After a luxury escape? Make your way to the filters to search for properties with a 5-star rating. If you have a fixed budget, select how much you want to spend and then browse our amazing options. We’ll help you find a suitable stay whatever your getaway looks like.
How can I find cheap condos in Middlebrook?
With Expedia’s handy filter tool, booking cheap condos in Middlebrook is a cinch. To discover properties that are easy on the wallet, narrow your search by budget, amenities and star rating.