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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

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

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

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

10.0 out of 10, Exceptional, (23)
"Great place for me, while dealing with a home issue. "
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
Alone Mill Schoolhouse - A paradise for outdoor lovers
Exterior

Alone Mill Schoolhouse - A paradise for outdoor lovers

9.6 out of 10, Exceptional, (191)
"Very fun getaway property. Well equipped kitchen, comfy beds, coffee makers and well heated/insulated in the wintry weather. Property is lovely for walks and must be amazing in all seasons. Close enough to Lexington for errands, far enough away to be secluded and quiet. Pool Table was a big hit!"
Alone Mill Schoolhouse - A paradise for outdoor lovers
Wintergreen Resort Post & Beam Home Beauty
Smart TV, fireplace, offices

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
Exterior

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

9.6 out of 10, Exceptional, (4)
"Clean, well stocked kitchen. Beds are queens and probably need new mattresses. Bedside tables are tiny. There is one bathroom upstairs with a small shower and one half bathroom downstairs. The A/C works well despite the high 90s each day. The large kitchen/dining area and TV area were perfect for our couples get together."
The price is SAR 532
SAR 1,441 total
includes taxes & fees
26 Mar - 27 Mar
Stay in Downtown Lex, Hot Tub, Walk to VMI, W&L
The Landmark: Luxury In Downtown Staunton
Fridge, microwave, oven, dishwasher

The Landmark: Luxury In Downtown Staunton

10.0 out of 10, Exceptional, (17)
"Great place for a group stay. Everything you need to cook if you wish. Street is a bit busy, parking limited to 2 vehicles."
The Landmark: Luxury In Downtown Staunton
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Terrace/patio

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

9.6 out of 10, Exceptional, (298)
"Our girls getaway was perfect! The house was just as described and very clean!!! I’m a stickler for clean and every nook and cranny was spotless. There was only one tiny inconvenience with the hot hub not being filled quite enough and maybe not cleaned before we came because of a film on the surface. But the owner/host responded immediately. We had everything we needed to fix the issue. The house is in a perfect location and located on a cul de sac, so very private. Would highly recommend and we...
The price is SAR 671
SAR 1,584 total
includes taxes & fees
13 Apr - 14 Apr
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub
Property grounds

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

9.0 out of 10, Wonderful, (2)
"The property is about a 5-7 minute drive to the Wintergreen resort. It was an excellent choice for multiple families who have kids. The downstairs area is full of entertaining games such as foosball, basketball, and darts. It also includes arcade games and multiple TVs. This area kept all the kids entertained whenever the adults were upstairs. "
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub
The All-American Cottage Seconds from Gypsy Hill Park! Kid and Pet friendly!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (11)
"Such a great property and the owners are great! The house is super close to everything and the neighborhood is great. We can’t wait to book again! "
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
Terrace/patio

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

10.0 out of 10, Exceptional, (88)
"The host was extremely responsive and very helpful with all questions prior to our arrival. Check in was easy with keyless access using a code provided and the space was very clean and comfortable. Kitchen was fully stocked with everything we would have needed, even some spices left by prior guests. The views from the screened in porch during a thunder storm were wonderful and the hot tub was very clean and great to have. We hiked around Natural Bridge one day then drove to Smith Mountain...
HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome
Insane Mountain Views - New Listing
Smart TV, fireplace, DVD player, books

Insane Mountain Views - New Listing

10.0 out of 10, Exceptional, (26)
"Imagine a house for 7 adult couples to relax, drink and be merry without feeling cramped. This house was absolutely astonishing. Each couple had a room with bathroom. The decor and upgrades, in every single room, offers inspiration and is 1,000% upscale.The great room view is breathtaking and the home is in close proximity to the slopes.This was my first time using VRBO and the owner was very responsive to all messages throughout the process. He has set the bar high.We will visit again!"
Insane Mountain Views - New Listing
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Outdoor spa tub

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!
Fridge, microwave, oven, stovetop

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
Exterior

Cozy Craftsman: Newly Renovated/Downtown Staunton

9.8 out of 10, Exceptional, (16)
"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 521
SAR 1,307 total
includes taxes & fees
1 Apr - 2 Apr
Cozy Craftsman: Newly Renovated/Downtown Staunton
The Firefly Springhouse
Exterior

The Firefly Springhouse

10.0 out of 10, Exceptional, (23)
"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."
The price is SAR 345
SAR 468 total
includes taxes & fees
26 Mar - 27 Mar
The Firefly Springhouse
Restored 1840 House with Gardens in Historic Downtown
Interior

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
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (59)
"Beautiful property a short drive from downtown. Very well equipped (so much coffee!), spacious, and comfortable. Lots of space indoors and out. Host was very responsive and helpful. Had a great time!"
Modern Farmhouse near VMI, W&L, SVU & VA Horse Ctr
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Terrace/patio

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

10.0 out of 10, Exceptional, (15)
"The property is in a quiet neighborhood close to town and all Waynesboro attractions. The home is stylishly decorated and the furnishings evoke memories of my younger years. Some even gave me a good laugh! The owners were responsive to our needs. The rental does not have a full kitchen, only a microwave and refrigerator, but is supplied with plates, cups, dinnerware and essential toiletries. The apartment is roomy and the bed was quite comfortable. The Loriann provided everything we needed for...
The price is SAR 341
SAR 610 total
includes taxes & fees
26 Mar - 27 Mar
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
White Rock Cabin
Property grounds

White Rock Cabin

10.0 out of 10, Exceptional, (202)
"Scott & Christie are excellent hosts. Everything was beyond expectations."
White Rock Cabin
Charming Basement apartment! Great for Families.
Interior

Charming Basement apartment! Great for Families.

10.0 out of 10, Exceptional, (1)
"The owner was amazing"
The price is SAR 371
SAR 559 total
includes taxes & fees
26 Mar - 27 Mar
Charming Basement apartment! Great for Families.
Spacious 5-bedroom house in a mountain hollow in Wintergreen Resort.
Fridge, microwave, oven, stovetop

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

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.

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

9.0 out of 10, Wonderful, (268)
"The date of my stay was Sun Feb 9 - Tues Feb 11, 2025. It was a great place to stay with beautiful views. Our stay was short. We were there for my son to participate in WASI- Wintergreen Alpine Special Invitational. Travel to the Mountain Inn for ski competition and celebration was easy. I really enjoyed having the full kitchen so we could make breakfast each day. The washer and dryer were helpful for keeping ski bibs clean and dry."
The price is SAR 394
SAR 910 total
includes taxes & fees
30 Mar - 31 Mar
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
2 bedrooms, iron/ironing board, travel crib, free WiFi

Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

10.0 out of 10, Exceptional, (36)
"We had such a nice getaway weekend at The Chestnut House. The Heiston’s went above and beyond to make our stay exceptional. The house was beautiful, cozy, and quiet. While sitting outside, the only thing we could hear was the relaxing sound of the river running through the backyard. The hosts made us feel very welcome and made it a wonderful experience. We would definitely book this home again. 10/10 recommend!"
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
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, (176)
"Area was nice, property grounds were clean, room was clean and laid out well. "
The price is SAR 398
SAR 443 total
includes taxes & fees
6 Apr - 7 Apr
Valley Extended 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.