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Middlebrook Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Middlebrook holiday rentals

Private kitchen
Affordable Suites of America Waynesboro

Apartment in Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
9.4 out of 10, Exceptional, (53 reviews)
"Always a pleasant stay."
United States
MARJORIE
The price is HK$647
HK$720 total
includes taxes & fees
13 Jan - 14 Jan
Affordable Suites of America Waynesboro
Terrace/patio
Bluebird Cottage: Near 151 + Appalachian Trail

Cottage in Roseland

Bluebird Cottage: Near 151 + Appalachian Trail
2.0 star property
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.
The price is HK$896
HK$2,276 total
includes taxes & fees
13 Jan - 14 Jan
Bluebird Cottage: Near 151 + Appalachian Trail
Exterior
Whimsical Creekside Cabin

Cabin in Vesuvius

Whimsical Creekside Cabin
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.
The price is HK$596
HK$1,496 total
includes taxes & fees
21 Jan - 22 Jan
Whimsical Creekside Cabin
Property grounds
The Firefly Springhouse

Holiday Home in Staunton

The Firefly Springhouse
9.8 out of 10, Exceptional, (47 reviews)
"Great cottage for 2 and peaceful setting. Host was helpful with great dinner recommendations "
United States
Joseph
The price is HK$645
HK$892 total
includes taxes & fees
13 Jan - 14 Jan
The Firefly Springhouse
Terrace/patio
Love Ridge Mountain Lodging

Cabin in Lyndhurst

Love Ridge Mountain Lodging
3.0 star property
10.0 out of 10, Exceptional, (14 reviews)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is HK$968
HK$1,555 total
includes taxes & fees
15 Jan - 16 Jan
Love Ridge Mountain Lodging
Outdoor spa tub
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Holiday Home in Waynesboro

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
9.6 out of 10, Exceptional, (45 reviews)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
The price is HK$912
HK$1,579 total
includes taxes & fees
19 Jan - 20 Jan
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Terrace/patio
Blair's Vintage Apartment Nestled in Wine Country

Apartment in Waynesboro

Blair's Vintage Apartment Nestled in Wine Country
10.0 out of 10, Exceptional, (23 reviews)
"Great experience. Host was great at communicating and made check in/check out super easy. She had everything we needed and way more. Location perfect for fly fishing the south river."
United States
Elpidio R.
The price is HK$764
HK$1,761 total
includes taxes & fees
13 Jan - 14 Jan
Blair's Vintage Apartment Nestled in Wine Country
Smart TV
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

Cottage in Buena Vista

The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
9.6 out of 10, Exceptional, (16 reviews)
"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.
The price is HK$779
HK$1,483 total
includes taxes & fees
13 Jan - 14 Jan
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Exterior
Laurelwood Hollow: Walk to Ski & Swim

Apartment in Wintergreen Resort

Laurelwood Hollow: Walk to Ski & Swim
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.
The price is HK$740
HK$2,176 total
includes taxes & fees
13 Jan - 14 Jan
Laurelwood Hollow: Walk to Ski & Swim
Lobby
The Bohemian Suite

Apartment in Staunton

The Bohemian Suite
2.0 star property
10.0 out of 10, Exceptional, (6 reviews)
"It was really nice. A bit pricey. "
United States
Bonny
The price is HK$694
HK$1,301 total
includes taxes & fees
13 Jan - 14 Jan
The Bohemian Suite
Fireplace
The Modern Mountain Condo

Condo in Wintergreen Resort

The Modern Mountain Condo
10.0 out of 10, Exceptional, (38 reviews)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
The price is HK$735
HK$1,841 total
includes taxes & fees
13 Jan - 14 Jan
The Modern Mountain Condo
Property grounds
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Condo in Wintergreen Resort

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
2.0 star property
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is HK$857
HK$1,961 total
includes taxes & fees
3 Feb - 4 Feb
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Fridge, microwave, oven, stovetop
Sweet Upstairs’s apartment right next to Southern Virginia University.

Apartment in Buena Vista

Sweet Upstairs’s apartment right next to Southern Virginia University.
10.0 out of 10, Exceptional, (24 reviews)
"Just as described. Cozy spot to spend a few days while we attended a wedding and visited family. "
United States
Lorrie H.
The price is HK$772
HK$1,119 total
includes taxes & fees
13 Jan - 14 Jan
Sweet Upstairs’s apartment right next to Southern Virginia University.
Interior
Downtown Luxe: Luxury Vintage + Downtown

Apartment in Staunton

Downtown Luxe: Luxury Vintage + Downtown
9.8 out of 10, Exceptional, (25 reviews)
"Charming property, ideally located with oodles of extra touches."
United States
Jonathan
The price is HK$928
HK$1,929 total
includes taxes & fees
13 Jan - 14 Jan
Downtown Luxe: Luxury Vintage + Downtown
Property grounds
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI

Holiday Home in Buena Vista

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
9.0 out of 10, Wonderful, (33 reviews)
"Nice place to stay"
United States
Ann E.
The price is HK$695
HK$1,664 total
includes taxes & fees
13 Jan - 14 Jan
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Terrace/patio
The Overlook: Walk Downtown + City Views

Apartment in Staunton

The Overlook: Walk Downtown + City Views
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.
The price is HK$928
HK$1,929 total
includes taxes & fees
13 Jan - 14 Jan
The Overlook: Walk Downtown + City Views
Fridge, microwave, oven, stovetop
Cozy Craftsman: Newly Renovated/Downtown Staunton

Holiday Home in Staunton

Cozy Craftsman: Newly Renovated/Downtown Staunton
9.8 out of 10, Exceptional, (32 reviews)
"Great house, walkable to town, easy check in and out, very clean, communicative hosts—couldn’t be better."
United States
Brooke L.
The price is HK$1,083
HK$2,724 total
includes taxes & fees
1 Feb - 2 Feb
Cozy Craftsman: Newly Renovated/Downtown Staunton
Fridge, microwave, oven, stovetop
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Condo in Wintergreen Resort

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
2.0 star property
9.8 out of 10, Exceptional, (7 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is HK$935
HK$2,355 total
includes taxes & fees
3 Feb - 4 Feb
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Smart TV, DVD player, books, music library
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cabin in Roseland

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
10.0 out of 10, Exceptional, (90 reviews)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is HK$1,013
HK$1,549 total
includes taxes & fees
13 Jan - 14 Jan
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Exterior
The Serendipity Suite

Apartment in Staunton

The Serendipity Suite
2.0 star property
10.0 out of 10, Exceptional, (6 reviews)
"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
The price is HK$694
HK$1,301 total
includes taxes & fees
13 Jan - 14 Jan
The Serendipity Suite
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

Country Inn & Suites by Radisson, Lexington, VA

Country Inn & Suites by Radisson, Lexington, VA

10/10 Excellent
"Very clean, breakfast area was well stocked and very clean. The room was amazing and the bed was very comfortable "
Rita 1-night trip
Posted 4 days ago
Country Inn & Suites by Radisson, Lexington, VA

Find out more about Middlebrook

Search for holiday rentals in Middlebrook on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlebrook using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middlebrook!

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?

Unbeatable Views Atop Wintergreen Resort: 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 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most 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 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.