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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, (285)
"We really enjoyed our stay Host Scott was very informative and has very clear information. The house is very family friendly. We loved being able to use the fireplace. The hot tub was spectacular my wife usually never likes Hot Tubs but used this one twice. Kids loved the indoor basketball hoops and pac-man . My wife grew up with pac-man so she really loved it. We booked the house for my BD and we had some great memories. We were very lucky ski resort was open so the kids loved that. Thank so...
The price is SAR 560
SAR 1,443 total
includes taxes & fees
13 Jan - 14 January 2025
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Newtown Retreat: Award-Winning Renovation + Ideal Location

10.0 out of 10, Exceptional, (18)
"My family and I enjoyed our stay. The home was well equipped with everything we needed and more making our stay very enjoyable and stress free. My kids loved having a variety of games to choose from as well. We stayed in and cooked most evenings in the spacious kitchen that was stocked with all essentials. I highly recommend this property! "
The price is SAR 1,427
SAR 2,268 total
includes taxes & fees
18 Jan - 19 January 2025
Newtown Retreat: Award-Winning Renovation + Ideal Location

Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!

10.0 out of 10, Exceptional, (1)
"- House is well taken care of. - House rule not wearing shoes inside and providing sleepers keeps the house clean. We liked it, but should mention that on VRBO listing. (It is listed on the competitors listing among the other info) Also, be better if the closed in shoes cabinet is available to protect the shoes from the weather. - Would be better if the property manager sent check-in info at least a day earlier than the middle of the day of check-in."
The price is SAR 1,878
SAR 3,856 total
includes taxes & fees
28 Dec - 29 Dec
Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!

Restored 1840 House with Gardens in Historic Downtown

9.8 out of 10, Exceptional, (128)
"We were in town to attend a Washington and Lee football game . This rental was perfect. The charm, decor and well stocked kitchen made the rental a solid 10. The location, parking, dog friendly atmosphere ,comfy bed, and vintage decor made it hard to check out. We will be back!"
Restored 1840 House with Gardens in Historic Downtown

White Rock Cabin

10.0 out of 10, Exceptional, (195)
"Absolutely beautiful location nice and tucked away. The hot tub was clean and a wonderful addition to the cute cabin feel. You can also hear the river from the hot tub :)"
White Rock Cabin

Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

9.8 out of 10, Exceptional, (68)
"We had a wonderful time at this home. Everything was accurate in its description. The driveway is extremely steep so I would be suspect in the winter of how to get up, but we had no problem this time of year."
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

4 BR cabin mins to trails & breweries pets welcome

9.6 out of 10, Exceptional, (20)
"A group of friends and I surprised my husband with a birthday get away trip. We all LOVED the house! It was clean and spacious. The host was super responsive. We even talked about booking this same house again in the future."
The price is SAR 1,052
SAR 2,696 total
includes taxes & fees
24 Dec - 25 Dec
4 BR cabin mins to trails & breweries pets welcome

Wintergreen Home w/ Hot Tub, Deck & Mountain Views

9.6 out of 10, Exceptional, (186)
"My husband and I met our son who goes to school in NC at this cabin to celebrate Thanksgiving together. The cabin was perfect and the views were amazing. I was able to cook us a Thanksgiving dinner while my Husband and son enjoyed the hot tub. We enjoyed our stay and would definitely book again!"
Wintergreen Home w/ Hot Tub, Deck & Mountain Views

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

10.0 out of 10, Exceptional, (38)
"We had an amazing stay and the home was perfect!! Everything was exactly as described and the place was well equipped for most anything you could ever need. We look forward to returning there soon for another relaxing getaway. "
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

COZY SKI COTTAGE--SKI IN SKI OUT

9.6 out of 10, Exceptional, (86)
"The house was great. We rented this ski in ski out for convenience with the kids being able to come and go. Because there was no snow, we had to drive to the lodge. This would have been a great location if this slope had been open. The owner was great and we would stay again."
COZY SKI COTTAGE--SKI IN SKI OUT

Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

9.8 out of 10, Exceptional, (170)
"Amazing views along the blue ridge trail in wintergreen. Host was communicative and check in was easy! Plentry of room for our stay and guests. We thouroughly enjoyed our stay!"
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

Spacious Lexington Home w/ Breathtaking Views

10.0 out of 10, Exceptional, (28)
"We loved it!"
Spacious Lexington Home w/ Breathtaking Views

HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome

10.0 out of 10, Exceptional, (82)
"The house in itself was absolutely perfect. Within a short trip to hikes and the Natural Bridge which was amazing. The owners were so nice and accommodating and in contact with us to make sure our stay was amazing. We will be booking a trip here again. "
HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome

Oak Tree Cottage: Beautiful farm with mountain views.

10.0 out of 10, Exceptional, (57)
"My family has stayed at this property a couple of times now and it is always a great experience! Clean and cozy and in a quiet location that is still convenient to shopping and activities. Highly recommend "
Oak Tree Cottage: Beautiful farm with mountain views.

Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

9.8 out of 10, Exceptional, (25)
"We have stay at Wintergreen many times, But this is the first time at this house. The owners were very responsive to questions we had and the house was in great shape and a joy to stay in. The views out the back were beautiful and the house inside very comfortable. Everything we could ask for. "
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

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

9.4 out of 10, Exceptional, (77)
"We loved staying in the treehouse! It was cozy and had everything we needed to make a perfect Thanksgiving meal! Everyone enjoyed the hiking and we even had a bit of snow on one of our hikes:) Thank you for helping us all enjoy our time together."
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

The Maury River House: A Luxury Country Experience

10.0 out of 10, Exceptional, (28)
"Our stay at the Maury House was exceptional. Thehost was accommodating ( we arrived an hour early) and available. The host responded to my questions immediately. The house is beautiful, well appointed, and had everything we needed in the kitchen, bathrooms, and bedrooms. There were seven in my group and the house could have held many more a d be very comfortable. Highly recommend! . .."
The Maury River House: A Luxury Country Experience

Nona's Cottage-Waynesboro/Shenandoah Valley, VA

10.0 out of 10, Exceptional, (17)
"Perfect for our visit to Waynesboro! Very clean and so close to downtown. We enjoyed the quiet neighborhood and nearness to the mountain hiking."
Nona's Cottage-Waynesboro/Shenandoah Valley, VA

Historic Raphine Retreat Near Brownsburg Village!

9.2 out of 10, Wonderful, (5)
"What a lovely, historic farmhouse! Our family enjoyed the beautiful setting and landscapes surrounding this adorable farmhouse. We were witness to beautiful sunrises and sunsets and our kiddos absolutely loved watching the cows move about on the fields around us. Highly recommend this little piece of serene history in the hills. "
Historic Raphine Retreat Near Brownsburg Village!

Spacious + Serene Mtn Top Escape, 4 En Suites

10.0 out of 10, Exceptional, (30)
"I enjoyed my stay here with family thoroughly. There are two balconies with beautiful views of the mountain. My 4 yo loved the muriel of the blue ridge on his bedroom wall. I loved that all bedrooms had an ensuite. Host was very responsive and accommodated our request."
The price is SAR 893
SAR 2,099 total
includes taxes & fees
22 Jan - 23 January 2025
Spacious + Serene Mtn Top Escape, 4 En Suites
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

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

9.0 out of 10, Wonderful, (256)
"My wife Teresa and I have been staying here for 11 years now. Every year for the last eleven years we have stayed the last week of Oct. The view is incredible. It never gets old. Something else that is very important to my wife and I is that the foyer door is only about 15 feet from the parking lot and its a flat walkway. Also, once in the foyer, its literally 2 steps to the stairs which are only 9 stairs. Most condos at Wintergreen are a hike just getting to the front door of the unit. Not...
The price is SAR 394
SAR 911 total
includes taxes & fees
5 Jan - 6 January 2025
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

9.6 out of 10, Exceptional, (285)
"We really enjoyed our stay Host Scott was very informative and has very clear information. The house is very family friendly. We loved being able to use the fireplace. The hot tub was spectacular my wife usually never likes Hot Tubs but used this one twice. Kids loved the indoor basketball hoops and pac-man . My wife grew up with pac-man so she really loved it. We booked the house for my BD and we had some great memories. We were very lucky ski resort was open so the kids loved that. Thank so...
The price is SAR 560
SAR 1,443 total
includes taxes & fees
13 Jan - 14 January 2025
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

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

10.0 out of 10, Exceptional, (298)
"This house was so beautiful! It was the best stocked vrbo we've stayed in with everything for the kitchen, bath, games and even a few dog toys! The hosts have thought of every little detail. Highly recommend. "
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
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.