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Middlebrook Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Middlebrook vacation rentals

A stone staircase leading to a wooden house with a door and a poster on the wall.

1. The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (70 reviews)
"Nice stay. Perfect for the solo traveler"
United States
David H
$103 nightly
The price is $114
Aug 31 - Sep 1
Total with taxes and fees
The Firefly Springhouse

2. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (253 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
$114 nightly
The price is $127
Aug 30 - Aug 31
Total with taxes and fees
Valley Extended Suites

3. The Bohemian Suite

The Bohemian Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (6 reviews)
"It was really nice. A bit pricey. "
United States
Bonny
$159 nightly
The price is $178
Aug 31 - Sep 1
Total with taxes and fees
The Bohemian Suite
A hallway with wooden flooring, a decorative birdcage, and two framed artworks on the walls.

4. Jungalu: Lush Jungle Retreat Downtown

Jungalu: Lush Jungle Retreat Downtown
Staunton
10.0 out of 10, Exceptional, (7 reviews)
"Everything was fantastic! The place was amazing and I loved the decor. The bed was very firm but the atmosphere was very inviting and clean. "
United States
Wendy W.
$194 nightly
The price is $217
Aug 30 - Aug 31
Total with taxes and fees
Jungalu: Lush Jungle Retreat Downtown

5. The Bohemian Suite: King Bed, Walk Downtown

The Bohemian Suite: King Bed, Walk Downtown
Staunton
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay at The Bohemian Suite! Close to everything and the space was beautiful. Would 100% stay here again when visiting my daughter at JMU "
United States
Jennifer M.
$182 nightly
The price is $204
Aug 31 - Sep 1
Total with taxes and fees
The Bohemian Suite: King Bed, Walk Downtown
A modern living room with a grey sofa, a wooden coffee table, and a red patterned rug.

6. Staunton Underground: Center of Downtown

Staunton Underground: Center of Downtown
Staunton
9.6 out of 10, Exceptional, (50 reviews)
"A charming property right near downtown with a modern kitchen and bathroom, and comfortable beds. It was cold while we were there and we particularly loved the heater in the bathroom. The hosts are wonderful and patient. I would happily book this property again."
United States
Hal A.
$215 nightly
The price is $241
Aug 30 - Aug 31
Total with taxes and fees
Staunton Underground: Center of Downtown
A two-story white house with green shutters, a front porch, and a small attached garage.

7. The Pop Inn: Family Destination, Walk Dwntwn

The Pop Inn: Family Destination, Walk Dwntwn
Staunton
9.8 out of 10, Exceptional, (34 reviews)
"Great attention to detail, and the "little things" that make you feel well cared for - like snacks and multiple ways to make coffee! Also very clean and such fun decor!"
United States
Betsey
$204 nightly
The price is $228
Aug 30 - Aug 31
Total with taxes and fees
The Pop Inn: Family Destination, Walk Dwntwn
A brick patio with steps leading to a seating area with blue metal chairs.

8. Blair's Vintage Apartment Nestled in Wine Country

Blair's Vintage Apartment Nestled in Wine Country
Waynesboro
10.0 out of 10, Exceptional, (28 reviews)
"Deborah was a remarkable host and responsive to all of our needs! If you are looking for a quiet and very clean place to rest - you’ve found it! The stocked fridge was icing on the cake!!"
United States
George S.
$204 nightly
The price is $227
Aug 30 - Aug 31
Total with taxes and fees
Blair's Vintage Apartment Nestled in Wine Country
A living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.

9. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (59 reviews)
"Nice resort"
United States
Diana J.
$166 nightly
The price is $187
Aug 31 - Sep 1
Total with taxes and fees
Where the Trail Ends
A two-story house with a deck, large windows, and a garage.

10. Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (23 reviews)
"This place was excellent. Very clean and quiet. Sherando lake was only 4 miles away with great hiking trails. The beds were very comfortable. Would definitely stay at this place again."
United States
Josh
$207 nightly
The price is $225
Sep 8 - Sep 9
Total with taxes and fees
Love Ridge Mountain Lodging
A wicker sofa with cushions, a wooden table, and a blue rug in a cozy outdoor seating area.

11. Downtown Luxe: Luxury Vintage + Downtown

Downtown Luxe: Luxury Vintage + Downtown
Staunton
10.0 out of 10, Exceptional, (39 reviews)
"Great property! Would definitely book again"
United States
Barzella P.
$227 nightly
The price is $254
Aug 30 - Aug 31
Total with taxes and fees
Downtown Luxe: Luxury Vintage + Downtown
A laundry room with two washers and two dryers, wooden beams on the ceiling, and a window with a view.

12. The Overlook: Walk Downtown + City Views

The Overlook: Walk Downtown + City Views
Staunton
10.0 out of 10, Exceptional, (41 reviews)
"The perfect location for a visit to Staunton. So much available within walking distance. The apartment is comfortable and it is great to have an outside space."
United States
Penny
$227 nightly
The price is $254
Aug 30 - Aug 31
Total with taxes and fees
The Overlook: Walk Downtown + City Views
A covered porch with wooden railings, a stone bench, and two lounge chairs.

13. The Serendipity Suite

The Serendipity Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (8 reviews)
"Electric charger and air-conditioning were key this weekend. Great location with easy walk to restaurants, entertainment and shops."
United States
Jennifer
$159 nightly
The price is $178
Aug 30 - Aug 31
Total with taxes and fees
The Serendipity Suite
A two-story house with a stone foundation, a large front porch, and a chimney.

14. Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Wintergreen Resort
10.0 out of 10, Exceptional, (122 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
$294 nightly
The price is $330
Aug 31 - Sep 1
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
A sandy beach with a lake and forested hills in the background.

15. House / hot tub/pet friendly

House / hot tub/pet friendly
Tyro
9.8 out of 10, Exceptional, (75 reviews)
"Very easy check in. We really enjoyed our stay!!"
United States
Mike B.
$297 nightly
The price is $334
Sep 8 - Sep 9
Total with taxes and fees
House / hot tub/pet friendly

16. "Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
Wintergreen Resort
10.0 out of 10, Exceptional, (42 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
$279 nightly
The price is $313
Aug 30 - Aug 31
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A cabin with a balcony overlooking a forested area and a stream.

17. Whimsical Creekside Cabin

Whimsical Creekside Cabin
Vesuvius
10.0 out of 10, Exceptional, (63 reviews)
"The place & everything was great!"
United States
Major G.
$241 nightly
The price is $277
Sep 21 - Sep 22
Total with taxes and fees
Whimsical Creekside Cabin
A kitchen with white cabinets, a stainless steel refrigerator, and a black countertop.

18. Green on New - Central Location and Staunton Charm

Green on New - Central Location and Staunton Charm
Staunton
9.6 out of 10, Exceptional, (19 reviews)
"The place was perfectly located, had everything we needed, extremely clean, maintained and down right adorable!"
United States
Tracy M.
$239 nightly
The price is $268
Sep 29 - Sep 30
Total with taxes and fees
Green on New - Central Location and Staunton Charm
A wooden pergola with string lights, a fire pit, and a hanging chair in a grassy outdoor area.

19. 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, (47 reviews)
"Nice place to stay"
United States
Ann E.
$178 nightly
The price is $205
Aug 30 - Aug 31
Total with taxes and fees
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
A wooden chair with a patterned cushion, a small table with a plant, and a wall with a chalkboard.

20. The Shenandoah Suite: Private Balcony, Walkable

The Shenandoah Suite: Private Balcony, Walkable
Staunton
9.8 out of 10, Exceptional, (25 reviews)
"As a frequent traveler to Staunton, this location has become my go-to for ease of access to everything the town has to offer. The decor and amenities are exactly what I need for a stress-free stay each time I am in town."
United States
Deborah
$181 nightly
The price is $203
Aug 30 - Aug 31
Total with taxes and fees
The Shenandoah Suite: Private Balcony, Walkable
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

Howard Johnson by Wyndham Lexington

Howard Johnson by Wyndham Lexington

10/10 Excellent
"Good room and amenities for the price we paid."
Patricia 1-night trip
Posted 2 hours ago
Howard Johnson by Wyndham Lexington

Find out more about Middlebrook

Everything you need to know about Middlebrook vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebrook vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlebrook vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlebrook vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlebrook. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middlebrook in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $127 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlebrook rentals

At Expedia, we put the best Middlebrook vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlebrook rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlebrook vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlebrook. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Middlebrook?

Yes, we offer vacation rentals near top attractions in Middlebrook, or you can select a more secluded option if you'd like a relaxing place to stay. Middlebrook is known for its parks.

What are some of the best vacation rentals in Middlebrook?

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI: This vacation home rental outside of Middlebrook is located in the mountains and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the arcade game room in this rental home to help you unwind.

What can I see and do in Middlebrook?

While exploring the area, visit family-friendly sights like Sunspots Studios Glassblowing, or get outside and enjoy nature at George Washington National Forest. In the larger area, you’ll find Staunton Railroad Station and Frontier Culture Museum.

What are vacation rentals like in Middlebrook?

Vacation rentals are private accommodations you can reserve for a couple days or more in Middlebrook. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip.