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Middlebrook Vacation Rentals

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Our top choices for Middlebrook vacation rentals

2.5 star property
9.4 out of 10, Exceptional, (53)
"Always a pleasant stay."
United States
MARJORIE
$83 nightly
The price is $92
Jan 19 - Jan 20
Total with taxes and fees
Affordable Suites of America Waynesboro
9.6 out of 10, Exceptional, (15)
"Nice clean house with comfortable beds. Perfect place for us while visiting Lexington. I hope to stay there again while in the area. Nicely updated interior with easy parking."
United States
Martin T.
$170 nightly
The price is $189
Jan 6 - Jan 7
Total with taxes and fees
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

Cabin in Lyndhurst

Love Ridge Mountain Lodging
3.0 star property
10.0 out of 10, Exceptional, (14)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
$189 nightly
The price is $205
Feb 4 - Feb 5
Total with taxes and fees
Love Ridge Mountain Lodging

Cabin in Vesuvius

Whimsical Creekside Cabin
10.0 out of 10, Exceptional, (43)
"Private cabin, super clean and neat. Nature was beautiful. Love the creek next to it! "
United States
Katherine V.
$168 nightly
The price is $194
Feb 5 - Feb 6
Total with taxes and fees
Whimsical Creekside Cabin
2.0 star property
8.4 out of 10, Very Good, (9)
"I contacted the owners to see if my family and I could check in earlier and they were about to accommodate for us. The home was clean, spacious, and had everything we needed for our stay."
United States
Sa'Mone M.
$275 nightly
The price is $292
Jan 12 - Jan 13
Total with taxes and fees
Bluebird Cottage: Near 151 + Appalachian Trail
9.6 out of 10, Exceptional, (45)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
$182 nightly
The price is $203
Jan 6 - Jan 7
Total with taxes and fees
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Vacation Home in Staunton

The Firefly Springhouse
9.8 out of 10, Exceptional, (45)
"Great cottage for 2 and peaceful setting. Host was helpful with great dinner recommendations "
United States
Joseph
$103 nightly
The price is $114
Jan 6 - Jan 7
Total with taxes and fees
The Firefly Springhouse

Chalet in Rockbridge Baths

NEW! The Nest near Goshen Pass
2.0 star property
10.0 out of 10, Exceptional, (2)
"My husband and I had a great stay. The treehouse cabin is beautiful and cozy! Everything was very clean and well planned for a perfect retreat! Highly recommend!"
United States
ashley m.
$180 nightly
The price is $208
Jan 7 - Jan 8
Total with taxes and fees
NEW! The Nest near Goshen Pass

Apartment in Staunton

The Bohemian Suite
2.0 star property
10.0 out of 10, Exceptional, (6)
"It was really nice. A bit pricey. "
United States
Bonny
$149 nightly
The price is $160
Jan 7 - Jan 8
Total with taxes and fees
The Bohemian Suite

Apartment in Wintergreen Resort

Laurelwood Hollow: Walk to Ski & Swim
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
$265 nightly
The price is $279
Jan 13 - Jan 14
Total with taxes and fees
Laurelwood Hollow: Walk to Ski & Swim
10.0 out of 10, Exceptional, (90)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
$175 nightly
The price is $197
Jan 6 - Jan 7
Total with taxes and fees
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
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 6 - Jan 7
Total with taxes and fees
Jade Dragon Guest House - Deerfield, VA. - Hamilton Branch River
10.0 out of 10, Exceptional, (59)
"Great place to stay. "
United States
Kelly H
$202 nightly
The price is $225
Jan 8 - Jan 9
Total with taxes and fees
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
9.6 out of 10, Exceptional, (7)
"The cabins are well maintained and located close to trail access for the Appalachian Trail and other state recreational activities."
United States
Darren B.
$185 nightly
The price is $208
Jan 8 - Jan 9
Total with taxes and fees
Dripping Rock--1 King BR, Jacuzzi, Kitchenette
9.0 out of 10, Wonderful, (305)
"Outstanding views from the deck!! Loved it!"
United States
Kerry M.
$215 nightly
The price is $241
Jan 6 - Jan 7
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.8 out of 10, Exceptional, (30)
"This was a great place for our short weekend getaway! We needed a place we could unplug, and that's exactly what we did reading by the fire, but there was plenty to do if we wanted to! We look forward to staying here again."
United States
Richard
$228 nightly
The price is $256
Jan 6 - Jan 7
Total with taxes and fees
Stylish-Updated-Central -Walk to Slopes-Dogs OK!

Apartment in Fishersville

Valley Extended Suites
3.0 star property
9.0 out of 10, Wonderful, (216)
"Nice stay"
United States
swati
$114 nightly
The price is $127
Jan 6 - Jan 7
Total with taxes and fees
Valley Extended Suites
10.0 out of 10, Exceptional, (4)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
$213 nightly
The price is $239
Jan 11 - Jan 12
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Apartment in Staunton

The Serendipity Suite
2.0 star property
10.0 out of 10, Exceptional, (6)
"Cute and tidy. Easy check in and out. Easy parking and walk to dining. EV charge is for teslas, you'll need an adapter."
United States
Jennifer
$149 nightly
The price is $160
Jan 7 - Jan 8
Total with taxes and fees
The Serendipity Suite
9.8 out of 10, Exceptional, (33)
"Had a great stay!"
United States
Erin C.
$276 nightly
The price is $318
Jan 6 - Jan 7
Total with taxes and fees
Rustic Romantic Bayberry Cottage at Autumn Ridge
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

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?

Unbeatable Views Atop Wintergreen Resort: This vacation home rental outside of Middlebrook is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games 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 Beverley Cigar Store, or get outside and enjoy nature at George Washington National Forest. In the larger area, you’ll find Frontier Culture Museum and American Shakespeare Center.

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.