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Middlebrook Holiday Rentals

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Check prices for these dates

Tonight
18 Jul - 19 Jul
Tomorrow
19 Jul - 20 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in Middlebrook

Cozy Cottage in the Woods-Firepit-BBQ-Games-Smores
Situated in a serene wooded area, this charming house features a traditional front porch and a well-manicured lawn.

Cozy Cottage in the Woods-Firepit-BBQ-Games-Smores

2.0 star property
7.6 out of 10, Good, (5)
"Great and peaceful place for a great getaway. "
The price is NZ$496
includes taxes & fees
20 July - 21 July
Cozy Cottage in the Woods-Firepit-BBQ-Games-Smores
Waynesboro Home Near Wintergreen Charlottesville
Enjoy cooking in this well-lit kitchen with a refrigerator, dishwasher, sink, and ample countertop space.

Waynesboro Home Near Wintergreen Charlottesville

2.0 star property
The price is NZ$975
includes taxes & fees
20 July - 21 July
Waynesboro Home Near Wintergreen Charlottesville
Charming Basement apartment! Great for Families.
Cozy retreat with a bunk bed, sofa, and comfortable seating area.

Charming Basement apartment! Great for Families.

9.4 out of 10, Exceptional, (6)
"The owner was amazing"
The price is NZ$233
includes taxes & fees
19 July - 20 July
Charming Basement apartment! Great for Families.
Updated, Cheerful Home Minutes to SVU, VMI and W&L
Relax by the fire pit surrounded by lush greenery and a cozy pergola.

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

9.0 out of 10, Wonderful, (26)
"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 NZ$357
includes taxes & fees
21 July - 22 July
Updated, Cheerful Home Minutes to SVU, VMI and W&L
Jade Dragon Guest House - Deerfield, VA. - Hamilton Branch River
Sit around the central fire pit in a tranquil outdoor setting.

Jade Dragon Guest House - Deerfield, VA. - Hamilton Branch River

9.6 out of 10, Exceptional, (4)
"A nice clean, relaxing place to stay."
The price is NZ$248
includes taxes & fees
22 July - 23 July
Jade Dragon Guest House - Deerfield, VA. - Hamilton Branch River
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Cozy retreat with a wooden desk, framed photograph, and a bird statue, surrounded by lush greenery and a classic mirror.

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

10.0 out of 10, Exceptional, (18)
"Beautiful home, very comfortable, and uniquely fun decor. Highly recommend!"
The price is NZ$255
includes taxes & fees
22 July - 23 July
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
The Firefly Springhouse
Access the upper level or storage area via the wooden staircase.

The Firefly Springhouse

10.0 out of 10, Exceptional, (30)
"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."
The price is NZ$192
includes taxes & fees
27 July - 28 July
The Firefly Springhouse
80s glam house w/ hot tub, mtn views near W&L, VMI
Open-plan living area with a high ceiling and exposed beams, featuring a dining area with a glass table and chairs, a kitchen with modern appliances, and a stone accent wall.

80s glam house w/ hot tub, mtn views near W&L, VMI

2.0 star property
10.0 out of 10, Exceptional, (7)
"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"
80s glam house w/ hot tub, mtn views near W&L, VMI
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Exterior

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

The price is NZ$320
includes taxes & fees
29 July - 30 July
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
Enjoy cooking in this well-equipped kitchen with a stainless steel range hood, window view, and convenient dishwashing machine.

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

10.0 out of 10, Exceptional, (38)
"Beautiful property and very responsive host. Nice place to stay. "
The price is NZ$506
includes taxes & fees
21 July - 22 July
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
Charming downtown Lex cottage, walk to WLU, VMI
Step into a traditional haven with a secure, entrance and a rustic stone building.

Charming downtown Lex cottage, walk to WLU, VMI

10.0 out of 10, Exceptional, (5)
"So charming and comfortable, this cottage provides absolutely everything one might need. Serene, uncluttered, well designed space…plus walkable to shoppes, great restaurants, church. Every aspect was well planned and thoughtful. Communication was super prompt, friendly and clear. We will absolutely book this again next time we visit Lexington. Highly, highly recommend. "
Charming downtown Lex cottage, walk to WLU, VMI
Hays Creek Cottage: Waterfront Home Near Mountains
Relax in a traditional room with a cozy seating area, featuring a bench and table with chairs.

Hays Creek Cottage: Waterfront Home Near Mountains

8.0 out of 10, Very good, (1)
"This lovely property is in an idyllic setting on a quiet country lane, across from a creek. We were delighted with the lodgings, and the amenities were outstanding. We had two little girls with us, who loved the flowers growing in the yard, and creek. It seemed as if all the furnishings were new, or nearly new, and the only negatives that I might mention, were that our bed was ultra firm ( a little too firm for me) . Overall, a very fine property, and every comfort has been thought out for...
The price is NZ$838
includes taxes & fees
17 Aug - 18 Aug
Hays Creek Cottage: Waterfront Home Near Mountains
Yurt at Stillhouse Farm *Wifi *Creek *Private *Less than 5 miles from VMI + W&L
Experience a loft-style retreat with a kitchen area, comfortable seating, and a fireplace.

Yurt at Stillhouse Farm *Wifi *Creek *Private *Less than 5 miles from VMI + W&L

10.0 out of 10, Exceptional, (48)
"The property was very clean and orderly, not too far from town but a good quiet stay. The owners were clear and organized with check in/out procedures and very good communication."
The price is NZ$489
includes taxes & fees
20 July - 21 July
Yurt at Stillhouse Farm *Wifi *Creek *Private *Less than 5 miles from VMI + W&L
Home with amazing location, 25min to Wintergreen, 30 min to Charlottesville, 20 min Staunton
Enjoy cooking in this well-equipped kitchen with a refrigerator, dishwasher, and microwave.

Home with amazing location, 25min to Wintergreen, 30 min to Charlottesville, 20 min Staunton

The price is NZ$1,019
includes taxes & fees
20 July - 21 July
Home with amazing location, 25min to Wintergreen, 30 min to Charlottesville, 20 min Staunton
The Hunker Down: Cheerful 2 Bed and Pet Friendly
Stylish two-story residence with a covered porch and balcony.

The Hunker Down: Cheerful 2 Bed and Pet Friendly

9.0 out of 10, Wonderful, (12)
"Really loved how everything was in easy walking distance."
The price is NZ$414
includes taxes & fees
6 Aug - 7 Aug
The Hunker Down: Cheerful 2 Bed and Pet Friendly
House / hot tub/pet friendly
Enjoy al fresco dining on the covered deck, surrounded by lush greenery and a charming wooden fence.

House / hot tub/pet friendly

9.8 out of 10, Exceptional, (60)
"Great mountain get-away. Owner was very quick to respond to questions. Good location for hiking and relaxation."
The price is NZ$494
includes taxes & fees
1 Aug - 2 Aug
House / hot tub/pet friendly
The Hawthorne Place
Exterior

The Hawthorne Place

10.0 out of 10, Exceptional, (2)
"Great con condition, beds very cozy, towels soft had many kitchen items that were helpful for breakfast. Would recommend to others. Great for family visiting student at the university."
The price is NZ$526
includes taxes & fees
20 July - 21 July
The Hawthorne Place
The Hawksbill Haus (w/ hot tub)
Enjoy cooking and food preparation in this well-equipped kitchen with a central island, ample storage, and a large window above the sink.

The Hawksbill Haus (w/ hot tub)

9.6 out of 10, Exceptional, (7)
"Home was as described. Location was close enough to stores and attractions. Hot tub was nice."
The price is NZ$557
includes taxes & fees
29 July - 30 July
The Hawksbill Haus (w/ hot tub)
Cabin on 2 acres River access, Fire Pit, & Hot tub
Relax in this spacious living area with a high ceiling, featuring a comfortable sofa, flat-screen TV, and wooden staircase.

Cabin on 2 acres River access, Fire Pit, & Hot tub

10.0 out of 10, Exceptional, (6)
"Stayed with friends for a W&L reunion. Great property."
The price is NZ$836
includes taxes & fees
24 July - 25 July
Cabin on 2 acres River access, Fire Pit, & Hot tub
Charming 2-bedroom condo in beautiful Wintergreen Resort
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range hood, microwave, and dishwasher.

Charming 2-bedroom condo in beautiful Wintergreen Resort

10.0 out of 10, Exceptional, (1)
"We stayed here for a couple of nights over July 4th and it was a nice short getaway. The condo is in a good location - 5 min walk to resort restaurants - and is very comfortable. The kitchen is well-equipped with plenty of cooking tools. The living room seating space was comfortable and allowed for just hanging out. We really enjoyed our stay! "
The price is NZ$640
includes taxes & fees
19 July - 20 July
Charming 2-bedroom condo in beautiful Wintergreen Resort
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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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.