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Compare 67 Cottages in Middlebrook with updated reviews, rates, and availability.

LONG TERM RENTAL ONLY: MIN.30 NITE STAY. VMI & W&L & VA HORSE CENTER - WELCOME!

10.0 out of 10, Exceptional, (52)
"My friends and I stayed here recently while in town for our college reunion. The location can’t be beat- easy access to downtown Lexington, W&L, VMI, the Chessie Trail, etc. We will be back!"
LONG TERM RENTAL ONLY: MIN.30 NITE STAY. VMI & W&L & VA HORSE CENTER - WELCOME!

Riverside Cottage with Canoe

9.8 out of 10, Exceptional, (43)
"Loved our time at the Riverside Cottage. Thank you for hosting us."
Riverside Cottage with Canoe

Cozy 'Nonny Cottage' Near Appalachian Trail!

9.6 out of 10, Exceptional, (16)
"My daughter and I absolutely loved our stay at Nonny Cottage. It was so peaceful to sit on the porch each morning and enjoy coffee while watching the deer! We took full advantage of the property's proximity to several trailheads. We love Crabtree Falls and even ventured to the Natural Bridge in Lexington. It was so nice to enjoy such a peaceful escape. The cottage was comfy, the kitchen had everything we needed, and loved being able to sleep with the windows open! Thank you fo a beautiful stay....
Cozy 'Nonny Cottage' Near Appalachian Trail!

Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.

10.0 out of 10, Exceptional, (9)
"We absolutely loved our stay at this charming cottage in Tyro, VA! The property is a true retreat, with a tranquil stream running through the yard and a spacious, fenced-in area that was perfect for enjoying the outdoors in privacy. The cottage itself was cozy, clean, and thoughtfully equipped with everything we needed for a relaxing getaway. The highlight was definitely the serene surroundings. Waking up to the sound of the stream and spending evenings in the large yard made us feel completely...
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.

The Firefly Cottage

9.8 out of 10, Exceptional, (25)
"Had a wonderful getaway! So enjoyed our time together, exploring Staunton, and spending quiet time on the property watching the farm animals. "
The Firefly Cottage

Breathtaking Views & Cozy Studio

10.0 out of 10, Exceptional, (5)
"Cute little cottage, exactly as in pictures. We never saw another person there for two days. The door was unlocked and we were on our own. It was exactly what we wanted."
Breathtaking Views & Cozy Studio

Deerfield Honeymoon Cottage at Autumn Ridge

10.0 out of 10, Exceptional, (34)
"Heather and the Autumn Ridge staff were amazing as always. This is my fifth or sixth stay over the last two years and I will miss this little slice of paradise!"
The price is SAR 845
SAR 1,468 total
includes taxes & fees
24 Dec - 25 Dec
Deerfield Honeymoon Cottage at Autumn Ridge

Serene Roseland Retreat Near Wintergreen Resort!

3.0 star property
Serene Roseland Retreat Near Wintergreen Resort!

Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

9.8 out of 10, Exceptional, (125)
"Absolutely perfect in every way! We brought our whole family to enjoy Thanksgiving a new way. "
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

HISTORIC MILL KEEPER'S HOUSE, FRONTING ALONG BUFFALO CREEK, ROCKBRIDGE CO. , VA

HISTORIC MILL KEEPER'S HOUSE, FRONTING ALONG BUFFALO CREEK, ROCKBRIDGE CO. , VA

Red Roof Cottage, a romantic mountain getaway. Great hiking and fishing.

10.0 out of 10, Exceptional, (30)
"Great for a couple or two. Literally had everything you could want. Very welcoming. Stayed in the fall before it got cold. Would love to be there in the winter with the fire burning!"
Red Roof Cottage, a romantic mountain getaway. Great hiking and fishing.

Make memories to last a lifetime.

10.0 out of 10, Exceptional, (113)
"Wonderful place to stay for cadet families!"
Make memories to last a lifetime.

"The Sparrow" at Historic Downtown Staunton

10.0 out of 10, Exceptional, (12)
"Adorable house, lovely host, wonderful location."
"The Sparrow" at Historic Downtown Staunton

Mountain Mindset: Hot Tub + 0.6 mile from Slopes

9.6 out of 10, Exceptional, (4)
"We enjoyed the impeccable details in the renovated space. Very comfortable and upscale. Highly recommend to others!"
Mountain Mindset: Hot Tub + 0.6 mile from Slopes

Autumn Ridge Cottages

2.5 star property
9.0 out of 10, Wonderful, (179)
"Very nicely appointed, clean, quiet, quaint, and close to family. "
The price is SAR 995
SAR 1,957 total
includes taxes & fees
29 Dec - 30 Dec
Autumn Ridge Cottages

Peaceful Raphine Cottage w/ Deck & Fireplace!

9.6 out of 10, Exceptional, (9)
"We enjoyed ourselves very much. Communication with the owner was seamless and easy. Property was a wonderful location with the backdrop of the mountains. Our family loved the house. It Provided a perfect Place for us to call home for a few days stay in Shenandoah Area. We look forward to an opportunity to stay here in the future. "
Peaceful Raphine Cottage w/ Deck & Fireplace!

Rustic Romantic Bayberry Cottage at Autumn Ridge

9.8 out of 10, Exceptional, (21)
"Very nice. Well equipped. Enjoyed our get away. "
The price is SAR 864
SAR 1,490 total
includes taxes & fees
24 Dec - 25 Dec
Rustic Romantic Bayberry Cottage at Autumn Ridge

Hot Tub! Charming Cottage hosted by Heather

10.0 out of 10, Exceptional, (1)
"Beds are comfortable. Rooms are clean and space is great for a group. We had all kitchen items needed for Thanksgiving. Loved the horses next door."
Hot Tub! Charming Cottage hosted by Heather

Twinleaf Honeymoon Cottage at Autumn Ridge

9.8 out of 10, Exceptional, (13)
"Closer than you think, no more than 10 minutes to anything!"
The price is SAR 845
SAR 1,468 total
includes taxes & fees
29 Dec - 30 Dec
Twinleaf Honeymoon Cottage at Autumn Ridge

Cottage on the Farm

10.0 out of 10, Exceptional, (2)
"It was so cute."
Cottage on the Farm
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.

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