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Search Vacation Homes in Middlebrook

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Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Middlebrook vacation homes

Fridge, microwave, oven, stovetop
Simple & spacious 1-bedroom basement living in Lexington. Close to W&L and VMI

Vacation Home in Lexington

Simple & spacious 1-bedroom basement living in Lexington. Close to W&L and VMI
10.0 out of 10, Exceptional, (4)
"Great location, cozy, quiet. Great accommodations "
United States
Kristen H.
$125 nightly
The price is $142
Dec 23 - Dec 24
Total with taxes and fees
Simple & spacious 1-bedroom basement living in Lexington. Close to W&L and VMI
Interior
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

Vacation Home in Waynesboro

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
10.0 out of 10, Exceptional, (19)
"Beautiful home, very comfortable, and uniquely fun decor. Highly recommend!"
United States
Melissa
$171 nightly
The price is $191
Dec 28 - Dec 29
Total with taxes and fees
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Fridge, microwave, oven, stovetop
Century old 4 bedroom close to SVU, sleeps 8.

Vacation Home in Buena Vista

Century old 4 bedroom close to SVU, sleeps 8.
9.4 out of 10, Exceptional, (29)
"Wonderful and charming home in Buena Vista."
United States
Natalie C.
$312 nightly
The price is $347
Jan 4 - Jan 5, 2026
Total with taxes and fees
Century old 4 bedroom close to SVU, sleeps 8.
Property grounds
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI

Vacation Home in Buena Vista

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
9.0 out of 10, Wonderful, (33)
"I didn’t realize that this was an entire house with full kitchen, and two bedrooms. A wonderful place near Buena Vista and Lexington."
United States
Matthew
$184 nightly
The price is $212
Dec 22 - Dec 23
Total with taxes and fees
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Exterior
The Firefly Springhouse

Vacation Home in Staunton

The Firefly Springhouse
9.8 out of 10, Exceptional, (44)
"Great cottage for 2 and peaceful setting. Host was helpful with great dinner recommendations "
United States
Joseph
$103 nightly
The price is $114
Dec 22 - Dec 23
Total with taxes and fees
The Firefly Springhouse
Terrace/patio
Stay in Downtown Lex, Hot Tub, Walk to VMI, W&L

Vacation Home in Lexington

Stay in Downtown Lex, Hot Tub, Walk to VMI, W&L
10.0 out of 10, Exceptional, (14)
"Great for trip to Lexington!"
United States
Matt T.
$379 nightly
The price is $430
Dec 22 - Dec 23
Total with taxes and fees
Stay in Downtown Lex, Hot Tub, Walk to VMI, W&L
Smart TV
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Vacation Home in Waynesboro

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
9.6 out of 10, Exceptional, (45)
"We enjoyed this cozy home during our annual trip to the area. Loved the charming, private backyard. Nearby vineyards and Blue Ridge Parkway were an added bonus. "
United States
Virginia W.
$198 nightly
The price is $220
Jan 6 - Jan 7, 2026
Total with taxes and fees
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Outdoor pool
Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!

Vacation Home in Waynesboro

Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!
10.0 out of 10, Exceptional, (8)
"Wonderful day we really enjoyed the pool and hot tub during our stay! This is centrally located and well furnished! The hosts were great with communication!"
United States
Cameron V.
$498 nightly
The price is $555
Dec 29 - Dec 30
Total with taxes and fees
Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!
Property grounds
Jade Dragon Guest House - Deerfield, VA. - Hamilton Branch River

Vacation Home in Deerfield

Jade Dragon Guest House - Deerfield, VA. - Hamilton Branch River
9.6 out of 10, Exceptional, (7)
"A nice clean, relaxing place to stay."
United States
Benjamin C.
$145 nightly
The price is $161
Jan 5 - Jan 6, 2026
Total with taxes and fees
Jade Dragon Guest House - Deerfield, VA. - Hamilton Branch River
Interior
Water Trough Hill - Views of Lexington

Vacation Home in Buena Vista

Water Trough Hill - Views of Lexington
10.0 out of 10, Exceptional, (54)
"Beautiful location! We loved watching the sunset views of the hills. The home is extremely clean, always a bonus!"
United States
Julie P.
$234 nightly
The price is $269
Dec 23 - Dec 24
Total with taxes and fees
Water Trough Hill - Views of Lexington
Dining
Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge

Vacation Home in Fairfield

Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge
2.0 star property
10.0 out of 10, Exceptional, (10)
"We had a great little break from the hustle and bustle of life. We are locals and it was nice to just get away for a few days"
United States
Don P.
$440 nightly
The price is $507
Dec 22 - Dec 23
Total with taxes and fees
Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge
Fridge, microwave, oven, stovetop
The Hawksbill Haus (w/ hot tub)

Vacation Home in Waynesboro

The Hawksbill Haus (w/ hot tub)
9.6 out of 10, Exceptional, (10)
"Home was as described. Location was close enough to stores and attractions. Hot tub was nice."
United States
Catherine D.
$304 nightly
The price is $338
Jan 7 - Jan 8, 2026
Total with taxes and fees
The Hawksbill Haus (w/ hot tub)
Fridge, microwave, oven, stovetop
Green on New - Central Location and Staunton Charm

Vacation Home in Staunton

Green on New - Central Location and Staunton Charm
9.4 out of 10, Exceptional, (13)
"Really enjoyed our stay! Very clean and quaint little place. Would stay again. "
United States
JANIE M.
$225 nightly
The price is $252
Jan 6 - Jan 7, 2026
Total with taxes and fees
Green on New - Central Location and Staunton Charm
Exterior detail
The Hunker Down: Cheerful 2 Bed and Pet Friendly

Vacation Home in Staunton

The Hunker Down: Cheerful 2 Bed and Pet Friendly
9.0 out of 10, Wonderful, (13)
"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.
$220 nightly
The price is $246
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Hunker Down: Cheerful 2 Bed and Pet Friendly
TV
Hays Creek Cottage: Waterfront Home Near Mountains

Vacation Home in Rockbridge Baths

Hays Creek Cottage: Waterfront Home Near Mountains
9.4 out of 10, Exceptional, (3)
"Very nice getaway. Clean peaceful, everything I wanted."
United States
Steve H.
$366 nightly
The price is $422
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hays Creek Cottage: Waterfront Home Near Mountains
Exterior
Cozy Cottage in the Woods-Firepit-BBQ-Games-Smores

Vacation Home in Millboro

Cozy Cottage in the Woods-Firepit-BBQ-Games-Smores
2.0 star property
8.6 out of 10, Excellent, (8)
"Great and peaceful place for a great getaway. "
United States
Renee P.
$336 nightly
The price is $367
Dec 22 - Dec 23
Total with taxes and fees
Cozy Cottage in the Woods-Firepit-BBQ-Games-Smores
Exterior
Charming downtown Lex cottage, walk to WLU, VMI

Vacation Home in Lexington

Charming downtown Lex cottage, walk to WLU, VMI
10.0 out of 10, Exceptional, (9)
"Super quaint and charming! Great location. Can walk to everything. "
United States
lori b.
$321 nightly
The price is $364
Jan 19 - Jan 20, 2026
Total with taxes and fees
Charming downtown Lex cottage, walk to WLU, VMI
Outdoor spa tub
Fox Hill: 151 Cottage w/Hot Tub + Mountain Views

Vacation Home in Afton

Fox Hill: 151 Cottage w/Hot Tub + Mountain Views
10.0 out of 10, Exceptional, (14)
"We had a wonderful stay! The long driveway made us feel tucked away in a forest. The home has an open floor plan on the first floor giving it a great feel. Beds were comfortable. We enjoyed the visit."
United States
Marisa R.
$455 nightly
The price is $511
Jan 13 - Jan 14, 2026
Total with taxes and fees
Fox Hill: 151 Cottage w/Hot Tub + Mountain Views
Exterior
Ridgeview Retreat: Mountain Views and Pet Friendly

Vacation Home in Staunton

Ridgeview Retreat: Mountain Views and Pet Friendly
10.0 out of 10, Exceptional, (12)
"Beautiful setting, very serene and quiet. "
United States
Beth H.
$399 nightly
The price is $444
Jan 5 - Jan 6, 2026
Total with taxes and fees
Ridgeview Retreat: Mountain Views and Pet Friendly
Interior
Yurt at Stillhouse Farm *Wifi *Creek *Private *Less than 5 miles from VMI + W&L

Vacation Home in Lexington

Yurt at Stillhouse Farm *Wifi *Creek *Private *Less than 5 miles from VMI + W&L
10.0 out of 10, Exceptional, (53)
"We really enjoyed our stay. Hope to return soon! "
United States
Denise W.
$271 nightly
The price is $312
Dec 22 - Dec 23
Total with taxes and fees
Yurt at Stillhouse Farm *Wifi *Creek *Private *Less than 5 miles from VMI + W&L
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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Top Middlebrook Hotel Reviews

Hotel 24 South

Hotel 24 South

10/10 Excellent
"Friendly staff, beautiful and clean room, nice indoor pool."
Alexander 1-night trip
Posted 3 days ago
Hotel 24 South

Find out more about Middlebrook

Middlebrook Vacation Homes information

Number of reviews
390
Accommodation
348 Vacation Homes
Lowest Price
$114
Highest Price
$555

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