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Middlebrook Vacation Rentals

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Vacation Rentals in Middlebrook

Valley Extended Suites

3.0 star property
Fishersville
9.0 out of 10, Wonderful, (215)
"I liked the cleanliness of the suite, the fully staffed kitchen, the large bathroom, the comfortable bed, the ease and safety of the parking area."
United States
Tammy
$114 nightly
The price is $127
Dec 1 - Dec 2
Total with taxes and fees
Valley Extended Suites

Love Ridge Mountain Lodging

3.0 star property
Montebello
10.0 out of 10, Exceptional, (12)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
$243 nightly
The price is $266
Dec 1 - Dec 2
Total with taxes and fees
Love Ridge Mountain Lodging

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Montebello
10.0 out of 10, Exceptional, (43)
"Nice quiet set of new cabins. Solid set of amenities. Really enjoyed our stay."
United States
Jesse C.
$203 nightly
The price is $228
Dec 1 - Dec 2
Total with taxes and fees
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Wow! What A View!

Wintergreen Resort
10.0 out of 10, Exceptional, (54)
"Very clean, very comfortable, easy to access - we honestly didn't want to leave."
United States
Josh W.
Wow! What A View!

New Build! Log Cabin with Hot Tub in Wintergreen

Chestnut Springs
10.0 out of 10, Exceptional, (4)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
New Build! Log Cabin with Hot Tub in Wintergreen

Whimsical Creekside Cabin

Vesuvius
9.8 out of 10, Exceptional, (39)
"Had a very quiet relaxing stay "
United States
Joyce I.
$171 nightly
The price is $197
Dec 2 - Dec 3
Total with taxes and fees
Whimsical Creekside Cabin

Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!

Wintergreen
10.0 out of 10, Exceptional, (251)
"The condo was absolutely lovely! We had great time in Wintergreen and will definitely go back. "
United States
Dawn C.
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

Wintergreen Resort
9.8 out of 10, Exceptional, (53)
"Great place to stay in Wintergreen!"
United States
Caroline w.
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome

Lexington
10.0 out of 10, Exceptional, (114)
"I had an excellent stay at this vrbo"
United States
Rashad W.
HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Wintergreen Resort
9.8 out of 10, Exceptional, (8)
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

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

Roseland
9.0 out of 10, Wonderful, (300)
"Great view!!"
United States
Suzanne W.
$210 nightly
The price is $236
Dec 1 - Dec 2
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Wintergreen. Sunset Vista Villa - Sea of Mountains

Wintergreen Resort
10.0 out of 10, Exceptional, (91)
"Beautiful property! Had everything we needed and was very clean! Highly recommend!"
United States
Amanda W.
$288 nightly
The price is $323
Dec 6 - Dec 7
Total with taxes and fees
Wintergreen. Sunset Vista Villa - Sea of Mountains

Cozy Cabin with private HOT TUB!

Nellysford
10.0 out of 10, Exceptional, (28)
"This location was a nice place to relax and enjoy family time."
United States
Melissa H.
Cozy Cabin with private HOT TUB!

Large and Luxurious Exec 5BR Chalet

Pedlars Edge
10.0 out of 10, Exceptional, (250)
"Perfect location for family ski trip"
United States
Angie S.
Large and Luxurious Exec 5BR Chalet

Alone Mill Schoolhouse - A paradise for outdoor lovers

Lexington
9.6 out of 10, Exceptional, (209)
"We loved everything about our stay! Absolutely cannot wait to stay again."
United States
Rachel M.
Alone Mill Schoolhouse - A paradise for outdoor lovers

Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

Wintergreen Resort
10.0 out of 10, Exceptional, (302)
"The home was very clean and beautiful. There were many great views in the mountains. Nathan and Kelly were very helpful with setting up tee times and getting pool passes. The resort has a few restaurants that were close and delicious. Wasn't chilly enough to use the fireplace but it did look inviting."
United States
Jack M.
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Roseland
10.0 out of 10, Exceptional, (335)
"Great stay, highly recommended"
United States
Jeffrey E.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

The Modern Mountain Condo

Wintergreen Resort
10.0 out of 10, Exceptional, (32)
"Fantastic stay at the Modern Mountain Condo! The check-in process was a breeze, the location is exactly as pictured and was very clean. Spacious location for a couples getaway. Host was extremely responsive to any questions and provided us great instructions and details about the space. Will stay again in the future! "
United States
Kelsey N.
$216 nightly
The price is $243
Dec 1 - Dec 2
Total with taxes and fees
The Modern Mountain Condo

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Roseland
9.6 out of 10, Exceptional, (142)
"Great stay in Wintergreen!"
United States
Pete K.
$222 nightly
The price is $249
Dec 1 - Dec 2
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Hiker’s paradise! Come relax this summer!!!

Roseland
10.0 out of 10, Exceptional, (36)
"Best place we have stayed around wintergreen hands down."
United States
Allen M.
Hiker’s paradise! Come relax this summer!!!
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?

HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome: This vacation home rental outside of Middlebrook is located in the mountains and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.