Photo by Brittany Davidson

Middlebrook Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Our top choices for Middlebrook vacation rentals

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
$398 nightly
The price is $422
Jan 15 - Jan 16
Total with taxes and fees
Blackwood Chalet

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (217 reviews)
"Nice stay"
United States
swati
$114 nightly
The price is $127
Jan 18 - Jan 19
Total with taxes and fees
Valley Extended Suites

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (15 reviews)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
$198 nightly
The price is $215
Jan 15 - Jan 16
Total with taxes and fees
Love Ridge Mountain Lodging

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (53 reviews)
"Always a pleasant stay."
United States
MARJORIE
$83 nightly
The price is $92
Jan 15 - Jan 16
Total with taxes and fees
Affordable Suites of America Waynesboro

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
2.0 star property
Wintergreen Resort
9.8 out of 10, Exceptional, (7 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
$271 nightly
The price is $304
Jan 15 - Jan 16
Total with taxes and fees
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (3 reviews)
"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 15 - Jan 16
Total with taxes and fees
Laurelwood Hollow: Walk to Ski & Swim

Whimsical Creekside Cabin

Whimsical Creekside Cabin
Vesuvius
10.0 out of 10, Exceptional, (44 reviews)
"Private cabin, super clean and neat. Nature was beautiful. Love the creek next to it! "
United States
Katherine V.
$166 nightly
The price is $192
Feb 2 - Feb 3
Total with taxes and fees
Whimsical Creekside Cabin

Bee Mountain Cabin fireplace, kitchen, jacuzzi

Bee Mountain Cabin fireplace, kitchen, jacuzzi
Lyndhurst
10.0 out of 10, Exceptional, (11 reviews)
"The cabin is lovely and the scenery is beautiful."
United States
Kimmy M.
$205 nightly
The price is $230
Jan 15 - Jan 16
Total with taxes and fees
Bee Mountain Cabin fireplace, kitchen, jacuzzi

NEW! The Nest near Goshen Pass

NEW! The Nest near Goshen Pass
2.0 star property
Rockbridge Baths
10.0 out of 10, Exceptional, (2 reviews)
"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.
$206 nightly
The price is $238
Jan 19 - Jan 20
Total with taxes and fees
NEW! The Nest near Goshen Pass

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

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (307 reviews)
"Outstanding views from the deck!! Loved it!"
United States
Kerry M.
$213 nightly
The price is $239
Jan 15 - Jan 16
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

The Storefront

The Storefront
3.5 star property
Staunton
8.8 out of 10, Excellent, (58 reviews)
"Great place to stay in charming Staunton!"
United States
Kate
$209 nightly
The price is $227
Jan 18 - Jan 19
Total with taxes and fees
The Storefront

Autumn Ridge Cottages

Autumn Ridge Cottages
2.5 star property
Lexington
9.0 out of 10, Wonderful, (180 reviews)
"Very nicely appointed, clean, quiet, quaint, and close to family. "
United States
Gary
$375 nightly
The price is $432
Jan 19 - Jan 20
Total with taxes and fees
Autumn Ridge Cottages

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, (33 reviews)
"Nice place to stay"
United States
Ann E.
$184 nightly
The price is $212
Jan 15 - Jan 16
Total with taxes and fees
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI

Wintergreen. Sunset Vista Villa - Close to the ski slopes

Wintergreen. Sunset Vista Villa - Close to the ski slopes
Wintergreen Resort
10.0 out of 10, Exceptional, (95 reviews)
"Fantastic stay again! Condo is perfect for a get away! "
United States
Jenna M.
$290 nightly
The price is $325
Jan 15 - Jan 16
Total with taxes and fees
Wintergreen. Sunset Vista Villa - Close to the ski slopes

Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail
2.0 star property
Roseland
8.4 out of 10, Very Good, (9 reviews)
"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 15 - Jan 16
Total with taxes and fees
Bluebird Cottage: Near 151 + Appalachian Trail

The Overlook: Walk Downtown + City Views

The Overlook: Walk Downtown + City Views
Staunton
10.0 out of 10, Exceptional, (30 reviews)
"House was nicely decorated, great location to town, and had all the amenities you would need to stay. "
United States
Stephanie P.
$222 nightly
The price is $249
Jan 15 - Jan 16
Total with taxes and fees
The Overlook: Walk Downtown + City Views

Wintergreen Ridge Retreat

Wintergreen Ridge Retreat
2.0 star property
Chestnut Springs
8.8 out of 10, Excellent, (5 reviews)
"Enjoyed our stay, the property was very nice, communicated with property manager regarding a few issues and they were responsive. Accommodated the number of guests we had. Could use a bigger parking area for amount of guests that could be accommodated. "
United States
Amy N.
$517 nightly
The price is $556
Feb 9 - Feb 10
Total with taxes and fees
Wintergreen Ridge Retreat

Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge

Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge
2.0 star property
Fairfield
9.8 out of 10, Exceptional, (11 reviews)
"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.
$433 nightly
The price is $499
Jan 15 - Jan 16
Total with taxes and fees
Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge

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

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.6 out of 10, Exceptional, (45 reviews)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
$182 nightly
The price is $203
Jan 19 - Jan 20
Total with taxes and fees
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
Verona
10.0 out of 10, Exceptional, (58 reviews)
"Great place to stay. "
United States
Kelly H
$203 nightly
The price is $226
Jan 19 - Jan 20
Total with taxes and fees
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
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

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.