Photo by Brittany Davidson

Holiday Rentals in Middlebrook

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Middlebrook

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (189)
"I liked that it's has regular door keys. Loved it!"
The price is €109
includes taxes & fees
15 Jul - 16 Jul
Valley Extended Suites

Log cabin with mountain VIEWS in Lexington! Near VA Horse Ctr, 8 mi from VMI/W&L

2.0 star property
10.0 out of 10, Exceptional, (13)
"Picturesque setting! Cabin was wonderful. Property manager was very responsive and helpful. Highly recommend!"
Log cabin with mountain VIEWS in Lexington! Near VA Horse Ctr, 8 mi from VMI/W&L

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

9.0 out of 10, Wonderful, (283)
"The condo has just the right amenities, nicely decorated, and yes, a million dollar view."
The price is €214
includes taxes & fees
20 Jul - 21 Jul
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

10.0 out of 10, Exceptional, (27)
"The cabins are great for couples. My wife and I had a great weekend here. If you are looking for a place to out away from things and quiet then I recommend it. "
The price is €198
includes taxes & fees
14 Jul - 15 Jul
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

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

9.6 out of 10, Exceptional, (40)
"Property was incredibly clean and well-maintained. Enjoyed this condo!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

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 €224
includes taxes & fees
14 Jul - 15 Jul
Love Ridge Mountain Lodging

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (308)
"Exactly as advertised. Clean, everything worked, great location."
The price is €337
includes taxes & fees
14 Jul - 15 Jul
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!

10.0 out of 10, Exceptional, (37)
"Beautiful property and very responsive host. Nice place to stay. "
The price is €264
includes taxes & fees
14 Jul - 15 Jul
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!

Whimsical Creekside Cabin

10.0 out of 10, Exceptional, (26)
"Had a very quiet relaxing stay "
The price is €207
includes taxes & fees
31 Jul - 1 Aug
Whimsical Creekside Cabin

Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking

10.0 out of 10, Exceptional, (12)
"The house was lovely. The location was great. Plenty of space for everyone. We really enjoyed this home."
Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking

Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views

9.8 out of 10, Exceptional, (48)
"Great place, easy to find, and quick drive to the Wontergreen Resort!"
Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views

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

10.0 out of 10, Exceptional, (100)
"We had a wonderful getaway at Deer Ridge. What a comfortable snd impeccably clean home! Highlights were morning coffee on the screened porch, evenings by the fire pit, and relaxing in the hot tub. Alex is a star host whose hospitality made our stay memorable. "
HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome

You deserve it all! Awesome Views, Comfy Condo, Elevator, & Shuttle Service!

9.8 out of 10, Exceptional, (183)
"Great condo with a great view, would definitely stay here again."
You deserve it all! Awesome Views, Comfy Condo, Elevator, & Shuttle Service!

Rustic Mountain Retreat-Bear Paw

9.8 out of 10, Exceptional, (227)
"Thanks for sharing your cabin with us! We loved the fireplace and had all the tools we needed for cozy meals."
Rustic Mountain Retreat-Bear Paw

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

9.6 out of 10, Exceptional, (128)
"This property is one of the best prperties we have ever stayed at. The owner is very responsive and goes the extra mile. We will definitely rent this property again!!"
The price is €216
includes taxes & fees
20 Jul - 21 Jul
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Luxury cabin in the woods, 2 bedrooms plus loft

10.0 out of 10, Exceptional, (176)
"Had a great stay! Will be back!"
Luxury cabin in the woods, 2 bedrooms plus loft

Meadow View Cabin, a deluxe log home near Lexington VA.

10.0 out of 10, Exceptional, (169)
"Great property. "
Meadow View Cabin, a deluxe log home near Lexington VA.

Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

10.0 out of 10, Exceptional, (50)
"Really cool property on the Piney River. Great fly fishing in the back yard. Tons of outdoor space- house itself is beautiful. Kids enjoyed their spring break hanging outside and fishing. "
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

10.0 out of 10, Exceptional, (134)
"Excellent house close to the slopes"
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

Updated, Cheerful Home Minutes to SVU, VMI and W&L

9.0 out of 10, Wonderful, (25)
"The property was easy to navigate to and the neighborhood was very quiet. It had a nice big yard and the theatre room was fun!"
The price is €189
includes taxes & fees
20 Jul - 21 Jul
Updated, Cheerful Home Minutes to SVU, VMI and W&L
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

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?

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.: This holiday home rental outside of Middlebrook is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Gypsy Hill Park. 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.