Middlebrook Holiday Rentals
House
10.0Exceptional
(109 Reviews)
1 Bedroom
2 Baths
2 Guests
1400 ft²
Parking
Ocean View
Balcony/Terrace
View
US $310/Night
7 Nights - US $2,167
House
- Virginia
- ·
- Spottswood
- 1.92 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
2131.25 ft²
- Parking
Internet
Child Friendly
Sports/Activities
US $277/Night
7 Nights - US $1,937
Bed & Breakfast
10.0Exceptional
(15 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Balcony/Terrace
Kitchen
US $216/Night
7 Nights - US $1,513
Cabin
10.0Exceptional
(61 Reviews)
2 Bedrooms
1 Bath
5 Guests
580 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $231/Night
7 Nights - US $1,614
House
- Virginia
- ·
- Rockbridge Baths
- 4.46 mi to center
9.8Exceptional
(7 Reviews)
3 Bedrooms
3 Baths
8 Guests
2701.74 ft²
- Parking
- Balcony/Terrace
Air Conditioner- Internet
US $333/Night
7 Nights - US $2,331
RV Rental
10.0Exceptional
(19 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $208/Night
7 Nights - US $1,457
House
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $403/Night
7 Nights - US $2,821
House
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
245 ft²
- Breakfast
- Kitchen
- Air Conditioner
- Internet
US $251/Night
7 Nights - US $1,755
Cabin
- Virginia
- ·
- Rockbridge Baths
- 4.72 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
550 ft²
Hot Tub- Parking
- Ocean View
- Balcony/Terrace
US $367/Night
7 Nights - US $2,567
Luxury Holiday Rentals in Middlebrook
Over 267+ Luxury Holiday Rentals in or Near Middlebrook
House
10.0Exceptional
(70 Reviews)
6 Bedrooms
3 Baths
15 Guests
5500 ft²
Private Pool- Parking
Pool- Ocean View
US $1,408/Night
7 Nights - US $9,855
New
House
7 Bedrooms
4 Baths
22 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,344/Night
7 Nights - US $9,409
House
5 Bedrooms
5 Baths
12 Guests
3500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,303/Night
7 Nights - US $9,123
House
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,056/Night
7 Nights - US $7,395
House
- Lexington
- ·
- Montebello
- 1.61 mi to center
3 Bedrooms
4 Baths
6 Guests
2807 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $878/Night
7 Nights - US $6,148
New
House
4 Bedrooms
1 Bath
8 Guests
18299 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $789/Night
7 Nights - US $5,521
House
- Lexington
- ·
- Montebello
- 1.84 mi to center
3 Bedrooms
3 Baths
6 Guests
2200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $624/Night
7 Nights - US $4,371
House
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Internet
Pet Friendly
US $586/Night
7 Nights - US $4,100
House
- Staunton
- ·
- Waynesboro
- 6.86 mi to center
10.0Exceptional
(28 Reviews)
3 Bedrooms
3 Baths
8 Guests
2900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $574/Night
7 Nights - US $4,016
Top-Rated Holiday Rentals with a Pool in Middlebrook
Over 54+ The Best Private Villas and Holiday Rentals in Middlebrook with a Pool
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $362/Night
7 Nights - US $2,532
Hotel
10.0Exceptional
(1 Review)
1 Bath
- Breakfast
- Parking
- Pool
- Air Conditioner
US $130/Night
7 Nights - US $913
Hotel
9.6Exceptional
(1197 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $151/Night
7 Nights - US $1,058
Hotel
9.6Exceptional
(1004 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $122/Night
7 Nights - US $851
Bed & Breakfast
- Lexington
- ·
- Steeles Tavern
- 0.16 mi to center
9.6Exceptional
(145 Reviews)
1 Bedroom
1 Bath
- Private Pool
- Breakfast
- Parking
- Pool
US $279/Night
7 Nights - US $1,952
Hotel
9.4Exceptional
(354 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $136/Night
7 Nights - US $952
Hotel
9.2Exceptional
(456 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $143/Night
7 Nights - US $1,003
Hotel
9.0Exceptional
(1003 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $117/Night
7 Nights - US $818
Hotel
8.9Fabulous
(818 Reviews)
15 Baths
- Private Pool
- Breakfast
EV Charge Station- Parking
US $129/Night
7 Nights - US $903
Pet-Friendly Holiday Rentals in Middlebrook
Over 62+ Pet-Friendly Holiday Rentals in or Near Middlebrook
House
10.0Exceptional
(51 Reviews)
4 Bedrooms
2 Baths
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $369/Night
7 Nights - US $2,583
Cabin
5.4Average
(116 Reviews)
6 Bedrooms
6 Baths
18 Guests
- Hot Tub
- Breakfast
- Parking
- Air Conditioner
US $67/Night
7 Nights - US $469
Apartment
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $421/Night
7 Nights - US $2,948
House
- Lexington
- ·
- Montebello
- 1.91 mi to center
9.6Exceptional
(51 Reviews)
3 Bedrooms
2 Baths
8 Guests
1450 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $323/Night
7 Nights - US $2,264
Bed & Breakfast
- Lexington
- ·
- Steeles Tavern
- 0.16 mi to center
5 Bedrooms
5 Baths
10 Guests
127.01 ft²
Oceanfront- Hot Tub
- Breakfast
- EV Charge Station
US $236/Night
7 Nights - US $1,652
New
Apartment
8.0Excellent
(1 Review)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $272/Night
7 Nights - US $1,904
House
10.0Exceptional
(30 Reviews)
3 Bedrooms
1 Bath
6 Guests
1080 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $270/Night
7 Nights - US $1,893
Cottage
10.0Exceptional
(24 Reviews)
3 Bedrooms
1 Bath
6 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $260/Night
7 Nights - US $1,819
New
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Pet Friendly
US $323/Night
7 Nights - US $2,258
Large Holiday Rentals and Private Villas in Middlebrook
Over 12+ Large Holiday Rentals and Private Villas in or Near Middlebrook
Cabin
- Virginia
- ·
- Spottswood
- 9.23 mi to center
10.0Exceptional
(42 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $470/Night
7 Nights - US $3,293
Bed & Breakfast
7.9Very Good
(12 Reviews)
8 Bedrooms
8 Baths
14 Guests
352.52 ft²
- Breakfast
- Parking
- Balcony/Terrace
- Air Conditioner
US $168/Night
7 Nights - US $1,176
House
- Virginia
- ·
- Rockbridge Baths
- 4.42 mi to center
10.0Exceptional
(15 Reviews)
4 Bedrooms
3 Baths
10 Guests
2754 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $376/Night
7 Nights - US $2,631
New
House
4 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Internet
- Child Friendly
US $312/Night
7 Nights - US $2,181
House
- Virginia
- ·
- Rockbridge Baths
- 3.66 mi to center
9.0Exceptional
(35 Reviews)
4 Bedrooms
1 Bath
13 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $290/Night
7 Nights - US $2,031
House
10.0Exceptional
(6 Reviews)
4 Bedrooms
3 Baths
10 Guests
2318 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $357/Night
7 Nights - US $2,499
House
10.0Exceptional
(64 Reviews)
5 Bedrooms
3 Baths
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $307/Night
7 Nights - US $2,146
House
10.0Exceptional
(20 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $324/Night
7 Nights - US $2,271
House
4 Bedrooms
4 Baths
16 Guests
1100 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $605/Night
7 Nights - US $4,235
Wheelchair Accessible Holiday Homes in Middlebrook
Over 35+ Wheelchair Accessible Holiday Homes in or Near Middlebrook
Hotel
3 Baths
- Parking
- Pool
- Kitchen
- Air Conditioner
US $598/Night
7 Nights - US $4,187
Hotel
8.9Fabulous
(889 Reviews)
6 Baths
362.38 ft²
- EV Charge Station
- Parking
- Balcony/Terrace
- Air Conditioner
US $101/Night
7 Nights - US $708
Hotel
9.2Exceptional
(1444 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $115/Night
7 Nights - US $805
Hotel
3 Baths
- Parking
- Pool
- Kitchen
- Air Conditioner
US $598/Night
7 Nights - US $4,187
Hotel
8.9Fabulous
(708 Reviews)
8 Baths
265.06 ft²
- Private Pool
- Parking
- Pool
- Air Conditioner
US $146/Night
7 Nights - US $1,019
Hotel
2 Baths
- Parking
- Pool
- Kitchen
- Air Conditioner
US $399/Night
7 Nights - US $2,791
Hotel
1 Bath
- Parking
- Pool
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,396
Hotel
1 Bath
- Parking
- Pool
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,396
Hotel
2 Baths
- Parking
- Pool
- Air Conditioner
- Internet
US $399/Night
7 Nights - US $2,791
Middlebrook Private Villas and Holiday Homes Under $200
Over 103+ Middlebrook Private Villas and Holiday Homes Under $200
Cottage
10.0Exceptional
(57 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $146/Night
7 Nights - US $1,021
Apartment
9.7Exceptional
(59 Reviews)
4 Bedrooms
4 Baths
8 Guests
583.94 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $199/Night
7 Nights - US $1,393
Apartment
10.0Exceptional
(8 Reviews)
1 Bedroom
1 Bath
- Parking
- Internet
- Child Friendly
Laundry
US $184/Night
7 Nights - US $1,286
House
9.8Exceptional
(67 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $114/Night
7 Nights - US $801
Bed & Breakfast
8.2Excellent
(32 Reviews)
3 Bedrooms
3 Baths
9 Guests
208.1 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $175/Night
7 Nights - US $1,225
Apartment
- Virginia
- ·
- Spottswood
- 0.71 mi to center
9.8Exceptional
(48 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $145/Night
7 Nights - US $1,017
Apartment
8.8Fabulous
(8 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $188/Night
7 Nights - US $1,317
New
Apartment
1 Bedroom
1 Bath
3 Guests
700 ft²
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $125/Night
7 Nights - US $877
House
- Virginia
- ·
- Spottswood
- 10.91 mi to center
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $139/Night
7 Nights - US $973
Instantly Bookable Holiday Homes in Middlebrook
Over 119+ Instantly Bookable Holiday Homes in or Near Middlebrook
House
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
271 ft²
- Breakfast
- Kitchen
- Air Conditioner
- Internet
US $238/Night
7 Nights - US $1,664
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
452 ft²
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $268/Night
7 Nights - US $1,873
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
284 ft²
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $251/Night
7 Nights - US $1,755
House
1 Bedroom
1 Bath
3 Guests
464 ft²
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $363/Night
7 Nights - US $2,538
House
- Virginia
- ·
- Spottswood
- 9.33 mi to center
9.6Exceptional
(29 Reviews)
4 Bedrooms
2 Baths
9 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $292/Night
7 Nights - US $2,045
House
10.0Exceptional
(67 Reviews)
1 Bedroom
1 Bath
2 Guests
708 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $209/Night
7 Nights - US $1,465
House
10.0Exceptional
(46 Reviews)
3 Bedrooms
3 Baths
8 Guests
1720 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $304/Night
7 Nights - US $2,130
Bed & Breakfast
10.0Exceptional
(42 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $221/Night
7 Nights - US $1,550
Cabin
10.0Exceptional
(39 Reviews)
3 Bedrooms
3 Baths
8 Guests
2669 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $452/Night
7 Nights - US $3,167
Book a Last Minute Place to Stay in Middlebrook
About Casai's Private Villas and Holiday Rentals in Middlebrook
Discover more than 276 vacation rentals available in Middlebrook. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Middlebrook.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Middlebrook, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Middlebrook. On average, places to stay near Middlebrook offer 483.41 ft², with nightly prices averaging US $267.
With Casai, finding and comparing holiday rentals in Middlebrook is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Middlebrook
| Type | Count |
|---|---|
| Vacation Homes | 115 |
| Holiday Apartments | 74 |
| Cottages | 6 |
Use these Quick Filters to Find a Holiday Rental in Middlebrook
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Middlebrook.
Weather in Middlebrook, VA
View the weather forecast for Middlebrook before booking your Middlebrook Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Middlebrook, VA
Casai offers a large selection of top attractions around Middlebrook . Research things to do on your vacation before you visit Middlebrook.
Frequently Asked Questions About Middlebrook?
What are the top holiday rentals in Middlebrook?
With numerous options available in Middlebrook, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Middlebrook:
- Hilltop Retreat. Amazing Views. Curated for Two.
- Cardinal Cottage Beautiful Shenandoah Valley getaway w/stunning mountain views
- Spacious Home, Private Pool, Tennis Court, Lake, Minutes From Town and Shopping
- Find out why this property is Almost Heaven
- Whimsical Creekside Cabin
- The Firefly Cottage
- Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
- Newtown Retreat — Award Winning Renovation + Ideal Location
- The Lodge at Joe Walker Hollow, privacy at its best with plenty of family space
- Bed&Breakfast in a 1795 Log Cabin on working farm, Margaret Baylor-Swoope suite
How many holiday rentals have private pools in Middlebrook?
Discover a selection of holiday rentals with private pools near Middlebrook with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Shenandoah Farm Stay POOL and GAME BARN
- Fairfield Inn & Suites by Marriott Staunton
- The Pool House: Mtn Views & 15 Mins to Downtown
- Pool/HotTub/Sauna/Grill/Private/Views/EVCharger
Which holiday homes in Middlebrook are best for families?
If you're searching for a family-friendly holiday home in Middlebrook, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Middlebrook:
- Panoramic mountain views and creekside walks in the beautiful Shenanodah Valley
- 'The Sanctuary' in Historic Dtwn Staunton
- The Serendipity Suite
How many Casai.nz holiday rentals are available in Middlebrook?
As of 2026, Casai boasts over 276 properties listed in the Middlebrook area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Middlebrook.
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