Holiday Homes in Middlebrook

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Middlebrook holiday homes

Beautiful 3-bedroom house with AC in charming Middlebrook

Beautiful 3-bedroom house with AC in charming Middlebrook
Middlebrook
The price is €269
includes taxes & fees
5 May - 6 May
Beautiful 3-bedroom house with AC in charming Middlebrook

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (58 reviews)
"The room was very clean and conveniently located for us."
United States
Jeanell S.
The price is €102
includes taxes & fees
4 May - 5 May
The Firefly Springhouse

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

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Waynesboro
10.0 out of 10, Exceptional, (20 reviews)
"The perfect stay for a wedding weekend in Waynesboro. It was very warm and accommodating and I can’t say enough good things about it. Thank you for a great weekend"
United States
Michael W.
The price is €177
includes taxes & fees
3 Jun - 4 Jun
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

NEW! Cheerful 2 bd bungalow with hot tub. Must see!

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.8 out of 10, Exceptional, (55 reviews)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
The price is €191
includes taxes & fees
3 Jun - 4 Jun
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (56 reviews)
"The place was very clean and spacious. The communication from the hosts was helpful. We had a very pleasant stay."
United States
James S.
The price is €323
includes taxes & fees
4 May - 5 May
Spacious + Serene Mtn Top Escape, 4 En Suites

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Buena Vista
9.0 out of 10, Wonderful, (37 reviews)
"Great stay. Nice property in a very quiet neighborhood. "
United States
Kurtis W.
The price is €176
includes taxes & fees
10 May - 11 May
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI

Fox Hill: Hot Tub, Views, Pet Friendly!

Fox Hill: Hot Tub, Views, Pet Friendly!
Afton
10.0 out of 10, Exceptional, (15 reviews)
"Everything was perfect. We needed a night away and this was the perfect place to end up."
United States
Dave D.
The price is €403
includes taxes & fees
4 May - 5 May
Fox Hill: Hot Tub, Views, Pet Friendly!

Jade Dragon Guest House - Deerfield, VA. - Hamilton Branch River

Jade Dragon Guest House - Deerfield, VA. - Hamilton Branch River
Deerfield
9.6 out of 10, Exceptional, (9 reviews)
"was a great stay! "
United States
Lane R.
The price is €158
includes taxes & fees
4 May - 5 May
Jade Dragon Guest House - Deerfield, VA. - Hamilton Branch River

The Farmhouse at Wellington: Waynesboro, Sleeps 12

The Farmhouse at Wellington: Waynesboro, Sleeps 12
Waynesboro
9.6 out of 10, Exceptional, (8 reviews)
"The house was convenient and the downstairs was big. Kitchen was wwkl stocked. Besrooms were just what we needed."
United States
Becky R.
The Farmhouse at Wellington: Waynesboro, Sleeps 12

Yurt at Stillhouse Farm *Wifi *Creek *Private *Less than 5 miles from VMI + W&L

Yurt at Stillhouse Farm *Wifi *Creek *Private *Less than 5 miles from VMI + W&L
Lexington
10.0 out of 10, Exceptional, (55 reviews)
"What a beautiful place! The hosts were wonderful and the yurt was welcoming, warm, and cozy. My family had a great time playing games and just spending quality time together. Definitely a place we’d visit again."
United States
Christina B.
The price is €263
includes taxes & fees
4 May - 5 May
Yurt at Stillhouse Farm *Wifi *Creek *Private *Less than 5 miles from VMI + W&L

"Glass & Pine" Home close to Bold Rock & Vineyards

"Glass & Pine" Home close to Bold Rock & Vineyards
Nellysford
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wished we could have stayed longer! The place was super clean and the views were beautiful once the rain finally stopped! Close to our favorite brewery and cidery. There were issues with TV reception (buffering) which may just be the area. Not much time for TV watching anyway with all the beautiful things to explore. We enjoyed our stay. "
United States
Robert H.
The price is €349
includes taxes & fees
6 May - 7 May
"Glass & Pine" Home close to Bold Rock & Vineyards

Hunker Down: Fenced in Yard, Pet Friendly!

Hunker Down: Fenced in Yard, Pet Friendly!
Staunton
9.0 out of 10, Wonderful, (13 reviews)
"We stayed here with our two kids (age 2 and 3) and would stay again! The apartment was incredibly clean with plenty of space and everything we needed. We sleep with white noise machines and had no issues with noise at all. Check in and parking was easy and the hosts were very responsive. "
United States
Michelle S.
Hunker Down: Fenced in Yard, Pet Friendly!

Oma's Garden Oasis: Spacious, Walk to Park

Oma's Garden Oasis: Spacious, Walk to Park
Staunton
9.8 out of 10, Exceptional, (31 reviews)
"Perfect location, comfortable bedding, and beautiful home! We absolutely loved our stay. We picked the perfect weekend to visit and enjoyed leaf pepping, downtown coffee shops, and Romeo and Juliet! "
United States
Crystal B.
The price is €359
includes taxes & fees
4 May - 5 May
Oma's Garden Oasis: Spacious, Walk to Park

Farmhouse at the foot of the Blue Ridge Mountains

Farmhouse at the foot of the Blue Ridge Mountains
Waynesboro
9.8 out of 10, Exceptional, (38 reviews)
"Great stay, my dog loved running around in the fenced backyard. "
United States
Caitlin P.
The price is €229
includes taxes & fees
6 May - 7 May
Farmhouse at the foot of the Blue Ridge Mountains

Beautiful 4-season Mountain Home- New Listing

Beautiful 4-season Mountain Home- New Listing
Wintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"The house was full of modern appliances, clean and very cozy. Plenty of space and in a great location. "
United States
Scott D.
Beautiful 4-season Mountain Home- New Listing

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (32 reviews)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!

Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
Vesuvius
9.8 out of 10, Exceptional, (46 reviews)
"Nice getaway, clean and well stocked. "
United States
Samuel
The price is €276
includes taxes & fees
4 May - 5 May
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!

Water Trough Hill - Views of Lexington

Water Trough Hill - Views of Lexington
Buena Vista
10.0 out of 10, Exceptional, (58 reviews)
"Everything was wonderful, thank you"
United States
Patricia F.
Water Trough Hill - Views of Lexington

Hike. Soak. Play. - Hot Tub, Sauna, Fire Pit & Game-Filled Fam Friendly Cabin

Hike. Soak. Play. - Hot Tub, Sauna, Fire Pit & Game-Filled Fam Friendly Cabin
Chestnut Springs
10.0 out of 10, Exceptional, (17 reviews)
"Perfect spot for a family retreat - highly recommend "
United States
Greg B.
Hike. Soak. Play. - Hot Tub, Sauna, Fire Pit & Game-Filled Fam Friendly Cabin

The Storefront

The Storefront
3.5 star property
Staunton
8.8 out of 10, Excellent, (58 reviews)
"Great location, fun place to stay!"
United States
Carol
The price is €194
includes taxes & fees
4 May - 5 May
The Storefront
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middlebrook Hotel Reviews

Find out more about Middlebrook

Middlebrook Holiday Homes information

Number of reviews
650
Accommodation
337 Holiday Homes
Lowest Price
€102
Highest Price
€403