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Compare 349 Vacation Homes in Middlebrook with updated reviews, rates, and availability.

Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

10.0 out of 10, Exceptional, (24)
"Enjoyed our stay. The sunrises and sunsets were great. House was fun. Don’t miss visiting the dairy farm across the street. Lovely. Perfect place for a relaxing time. "
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

Alone Mill Schoolhouse - A paradise for outdoor lovers

9.6 out of 10, Exceptional, (192)
"The location of the property is secluded just as we'd hope for. There's a really cute creek and fire pit to sit and enjoy nature and silence. There's plenty of space indoors for everyone not to feel too cramped together if your traveling with company. The fact we could bring our dogs with us was a huge bonus. I read reviews saying the beds were awful, they are not .they are traditional mattresses, but even my picky sleeper husband slept just fine with no a"
Alone Mill Schoolhouse - A paradise for outdoor lovers

Wintergreen Resort Post & Beam Home Beauty

9.8 out of 10, Exceptional, (18)
"Terrific, well appointed, every thing we needed. "
Wintergreen Resort Post & Beam Home Beauty

Stay in Downtown Lex, Hot Tub, Walk to VMI, W&L

9.6 out of 10, Exceptional, (5)
"if you desire to stay in downtown Lexington, I highly recommend this property. It is clean, spacious, and has any amenity needed to enjoy a great getaway experience. The check-in was super easy, and the staff quick to respond to any question. Last but not least, the property possesses an interesting history! We hope to enjoy a repeat in the near future."
The price is SAR 716
SAR 1,680 total
includes taxes & fees
21 Apr - 22 Apr
Stay in Downtown Lex, Hot Tub, Walk to VMI, W&L

The Landmark: Luxury In Downtown Staunton

10.0 out of 10, Exceptional, (18)
"We had a great stay at the Landmark. The home is lovely, well appointed, and was (thankfully!) very clean. Check in/out and communication were fast and easy!"
The Landmark: Luxury In Downtown Staunton

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

9.6 out of 10, Exceptional, (300)
"Exactly as advertised. Clean, everything worked, great location."
The price is SAR 672
SAR 1,584 total
includes taxes & fees
18 Apr - 19 Apr
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub

9.6 out of 10, Exceptional, (4)
"The house was very clean and a great location for eats and drinks. "
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub

The All-American Cottage Seconds from Gypsy Hill Park! Kid and Pet friendly!

10.0 out of 10, Exceptional, (12)
"My mother and I had a delightful weekend stay at this charming cottage while attending my daughter's baby shower. The cottage was everything we needed-clean, comfortable, and well-equipped. It was a one-level home with a front entrance ramp which made it especially convenient for my elderly mother to navigate. We felt right at home in the peaceful atmosphere. The hosts were welcoming and attentive, ensuring we had everything we needed for a comfortable visit. We would definitely recommend...
The All-American Cottage Seconds from Gypsy Hill Park! Kid and Pet friendly!

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

10.0 out of 10, Exceptional, (90)
"We had a wonderful getaway at Deer Ridge. What a comfortable snd impeccably clean home! Highlights were morning coffee on the screened porch, evenings by the fire pit, and relaxing in the hot tub. Alex is a star host whose hospitality made our stay memorable. "
HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome

Insane Mountain Views - New Listing

10.0 out of 10, Exceptional, (27)
"There are not enough adjectives in the dictionary to describe this AMAZING home! The views are literally the best in the area! The home was stunning- the layout, convenience, furniture, fixtures, amenities-it was as close to perfection as you can get. Our large Italian family travels a lot and have rented some lavish homes, but we all agreed this was THE BEST OVERALL we have ever stayed in! The owner was also super informative and super quick to respond to messages- and even let us have one...
Insane Mountain Views - New Listing

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!!!

Book for Spring! Nelson 151, MTN views!

10.0 out of 10, Exceptional, (14)
"We had such a nice relaxing vacation. The views were beautiful. Great resource provided for local activities, trails, restaurants, etc."
Book for Spring! Nelson 151, MTN views!

Cozy Craftsman: Newly Renovated/Downtown Staunton

9.8 out of 10, Exceptional, (17)
"The Cozy Cottage was the perfect home for my husband & I and our friends who joined us for a last minute weekend antique shopping in the area. The location was so close to all the dining & shopping downtown. The home was extremely clean & had everything we needed to feel right at home. We enjoyed our time there and will definitely be back. If we had known this home was so comfortable we would have added an extra day to our trip to simply enjoy a day at home relaxing! "
The price is SAR 522
SAR 1,315 total
includes taxes & fees
21 Apr - 22 Apr
Cozy Craftsman: Newly Renovated/Downtown Staunton

The Firefly Springhouse

10.0 out of 10, Exceptional, (24)
"Exactly as described. Nice property and a short distance from downtown and hiking. Enjoyed the animals on property as well as interaction w hosts."
The price is SAR 345
SAR 468 total
includes taxes & fees
19 Apr - 20 Apr
The Firefly Springhouse

Restored 1840 House with Gardens in Historic Downtown

9.8 out of 10, Exceptional, (132)
"This home is perfect for a larger group staying in Lexington. The home was very clean, well equipped and the beds were very comfortable. I would love to visit in the warmer months to take advantage of the porch and garden area. Being within walking distance of everything in town was so convenient. Peter was quick to reply when I contacted with questions. I highly recommended property!"
Restored 1840 House with Gardens in Historic Downtown

Modern Farmhouse near VMI, W&L, SVU & VA Horse Ctr

9.8 out of 10, Exceptional, (60)
"We loved our stay here! The house itself is charming and clean. And we loved the porch with the rocking chairs and the view. My daughter loved the goats, chickens and swim. We all enjoyed the hammock and fire pit. It was a fantastic stay and we hope to come back again. "
Modern Farmhouse near VMI, W&L, SVU & VA Horse Ctr

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

10.0 out of 10, Exceptional, (16)
"Amazing! I could spend hours at examining the decorations that each seem to have a story of their own. No detail overlooked! Felt like a step into the past ☺️"
The price is SAR 450
SAR 731 total
includes taxes & fees
20 Apr - 21 Apr
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

White Rock Cabin

10.0 out of 10, Exceptional, (204)
"We recently stayed here in early April 2025. We got to experience amazing spring blooms from native flowers, a beautiful and remote home, quiet atmosphere and surroundings, complete with excellent proximity to a number of outdoor activities.Our hosts were very thoughtful, helpful, and provided plenty of suggestions and tips for the area as well as a clean home with board games, views, amenities, etc.I couldn't recommend this home more and we will assuredly make it a point to return to this home,...
White Rock Cabin

Charming Basement apartment! Great for Families.

8.0 out of 10, Very Good, (2)
"The owner was amazing"
The price is SAR 371
SAR 560 total
includes taxes & fees
21 Apr - 22 Apr
Charming Basement apartment! Great for Families.

Spacious 5-bedroom house in a mountain hollow in Wintergreen Resort.

10.0 out of 10, Exceptional, (3)
"From the moment I stepped into this spacious, yet cozy property I knew it was going to be a wonderful weekend. I had arranged this weekend to celebrate a soon to be “mother of the bride” and mutual friends. The home was absolutely immaculate! No musty mountain smell that I have experienced in other homes located among the trees. Furnishings were updated and comfortable. The kitchen was very well stocked with lots of dish-ware, cookware, and utensils. The linens and towels are hotel quality. Such...
Spacious 5-bedroom house in a mountain hollow in Wintergreen Resort.
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, (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
21 Apr - 22 Apr
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

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
20 Apr - 21 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.