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Middlebrook Holiday Rentals

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Holiday Rentals in Middlebrook

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (205)
"Nice stay"
The price is NZ$204
includes taxes & fees
14 Oct - 15 Oct
Valley Extended Suites

Wow! What A View!

10.0 out of 10, Exceptional, (53)
"Property was gorgeous with amazing mountain views! Comfortable beds, beautiful kitchen and large living room for relaxing. Great location. Can’t wait to stay here again!"
Wow! What A View!

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

10.0 out of 10, Exceptional, (35)
"Great property and host"
The price is NZ$396
includes taxes & fees
15 Oct - 16 Oct
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

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

9.0 out of 10, Wonderful, (293)
"Will certainly look to book again in the future. Very nice condo with a spectacular view."
The price is NZ$424
includes taxes & fees
19 Oct - 20 Oct
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing stay I had, very peaceful and very quiet. "
The price is NZ$524
includes taxes & fees
15 Oct - 16 Oct
Love Ridge Mountain Lodging

Rustic Mountain Retreat-Bear Paw

9.8 out of 10, Exceptional, (230)
"The river access is top notch. Great location near a bunch of hikes. A perfect, peaceful spot for a weekend. "
Rustic Mountain Retreat-Bear Paw

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

10.0 out of 10, Exceptional, (244)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

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

10.0 out of 10, Exceptional, (329)
"The property is nestled very nicely on the mountain and convenient to the main lodge, restaurants and other attractions. We really enjoyed our stay. The condo was plenty big for the two of us and our dog. It is well-appointed Kudos to the owner, Heather, for thinking of everything to make our stay great. "
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

10.0 out of 10, Exceptional, (63)
"Loved our stay - the house, location, and amenities were perfect for us!"
The price is NZ$1,246
includes taxes & fees
14 Oct - 15 Oct
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Lovely C.1890 Flat with Garden in Historic Downtown

9.8 out of 10, Exceptional, (69)
"Great location! Great stay!"
The price is NZ$417
includes taxes & fees
19 Oct - 20 Oct
Lovely C.1890 Flat with Garden in Historic Downtown

Escape to the Blue Ridge Mountains at Wine-tergreen!

9.8 out of 10, Exceptional, (120)
"The condo was very nice . Had all the conveniences you need but, not really for over 60 years of age. Loved the area didn’t like the stairs. Would recommend it to anyone not old."
The price is NZ$430
includes taxes & fees
14 Oct - 15 Oct
Escape to the Blue Ridge Mountains at Wine-tergreen!

Cozy Cabin with private HOT TUB!

10.0 out of 10, Exceptional, (26)
"This location was a nice place to relax and enjoy family time."
Cozy Cabin with private HOT TUB!

The Modern Mountain Condo

10.0 out of 10, Exceptional, (29)
"Ideal location for skiing at Wintergreen. "
The price is NZ$420
includes taxes & fees
15 Oct - 16 Oct
The Modern Mountain Condo

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

9.8 out of 10, Exceptional, (13)
"Cabin was clean and tidy. Everything i needed was there. I felt comfortable and safe. This is important because I was traveling alone. This feels like it will be my get away spot in the future. Host was polite and quick to respond"
The price is NZ$396
includes taxes & fees
19 Oct - 20 Oct
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

10.0 out of 10, Exceptional, (7)
The price is NZ$335
includes taxes & fees
13 Oct - 14 Oct
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort

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

9.6 out of 10, Exceptional, (137)
"Very clean place and very accommodating host"
The price is NZ$434
includes taxes & fees
2 Nov - 3 Nov
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

9.6 out of 10, Exceptional, (50)
"Great place to stay for a relaxing weekend in the mountains to escape the heat. Greatly appreciated the fully stocked kitchen! It is truly fully stocked, unlike so many rental places which only claim to be. "
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

New Build! Log Cabin with Hot Tub in Wintergreen

10.0 out of 10, Exceptional, (2)
"Well appointed kitchen, beautiful cabin!"
The price is NZ$2,244
includes taxes & fees
16 Oct - 17 Oct
New Build! Log Cabin with Hot Tub in Wintergreen

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

9.8 out of 10, Exceptional, (54)
"This was our second stay in Wintergreen. First time at this property. The condo was beautifully decorated, had all the necessities and the view was breathtaking. "
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebrook holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlebrook holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebrook holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebrook holiday rentals we have selected for you start as low as NZ$204 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlebrook rentals

At Expedia, we put the best Middlebrook holiday 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 holiday.

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 holiday rentals in Middlebrook?

Yes, there are holiday rentals close to the most popular sights in Middlebrook, or you can select a more secluded option if you're looking for a relaxing stay. Middlebrook is known for its parks.

What are some of the best holiday rentals that Middlebrook has to offer?

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!: This holiday home rental outside of Middlebrook is located in the mountains, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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 wider area, you’ll find Frontier Culture Museum and American Shakespeare Center.

What are holiday rentals like in Middlebrook?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlebrook. Holiday rentals offer amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.