Deals on vacations and trips to Middlebrook

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Middlebrook flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
Price was $666, price is now $632 per person
$632
per person
Apr 3 - Apr 6
found 13 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Weyers Cave (SHD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Waynesboro Home Near Wintergreen Charlottesville

Waynesboro Home Near Wintergreen Charlottesville

2 out of 5
Price was $1,655, price is now $1,517 per person
$1,517
per person
Apr 3 - Apr 6
found 13 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Weyers Cave (SHD)
This vacation home features free WiFi in public areas, a garden, and barbecue grills.
Massanutten's Regal Vistas by Tripforth

Massanutten's Regal Vistas by Tripforth

3.5 out of 5
Price was $1,189, price is now $1,110 per person
$1,110
per person
Apr 3 - Apr 6
found 13 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Weyers Cave (SHD)
This vacation home features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Multilingual staff can provide around-the-clock assistance and barbecue grills are on offer.
Iris Inn and Cabins

Iris Inn and Cabins

4 out of 5
Price was $1,088, price is now $1,029 per person
$1,029
per person
Apr 3 - Apr 6
found 13 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Weyers Cave (SHD)
A restaurant and a bar/lounge are featured at this resort. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.
Massanuttens Shenandoah Villas by Tripforth

Massanuttens Shenandoah Villas by Tripforth

4 out of 5
Price was $906, price is now $858 per person
$858
per person
Apr 3 - Apr 6
found 13 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Weyers Cave (SHD)
This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. There's a picnic area and multilingual staff can provide around-the-clock assistance.

Top Middlebrook hotels deals

Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street Staunton VA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $123 total per night
$123 total
Mar 3 - Mar 4
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, a 24-hour business center, and a lobby fireplace are also offered.
Pool
Pet friendly
Motel 6 Staunton, VA

Motel 6 Staunton, VA

2 out of 5
96 Baker Lane Staunton VA
Free Cancellation
Reserve now, pay when you stay
$63 nightly
The price is $70 total per night
$70 total
Mar 15 - Mar 16
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli, express check-out, and dry cleaning are also on offer.
Pet friendly
Parking included
Holiday Inn Express & Suites Waynesboro East by IHG

Holiday Inn Express & Suites Waynesboro East by IHG

2.5 out of 5
108 Chicurel Lane Waynesboro VA
Free Cancellation
$107 nightly
The price is $119 total per night
$119 total
Mar 1 - Mar 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Enjoy the free buffet breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.
Pool
Breakfast included
Wingate by Wyndham Lexington

Wingate by Wyndham Lexington

2.5 out of 5
1100 N Lee Hwy Lexington VA
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $97 total per night
$97 total
Mar 5 - Mar 6
Total with taxes and fees
This hotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Hot Tub
Days Inn by Wyndham Waynesboro

Days Inn by Wyndham Waynesboro

2 out of 5
2060 Rosser Avenue/I-64 Waynesboro VA
Free Cancellation
Reserve now, pay when you stay
$54 nightly
The price is $60 total per night
$60 total
Mar 3 - Mar 4
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and barbecue grills are also on offer.
Pet friendly
Parking included
Best Western Plus Waynesboro Inn & Suites Conference Center

Best Western Plus Waynesboro Inn & Suites Conference Center

2.5 out of 5
109 Apple Tree Ln Waynesboro VA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $88 total per night
$88 total
Mar 1 - Mar 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center, conference center, and conference space. There's a 24-hour gym on site, and laundry facilities and free newspapers are also offered.
Breakfast included
Pet friendly
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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.

Frequently asked questions

How much are vacation packages to Middlebrook?
Vacation packages, which include flights and hotels in Middlebrook, start from as low as $632. Make your travel dreams a reality and lock in your trip with Travelocity today.
Where can I get the best vacation package deals for Middlebrook?
There are sensational Middlebrook package deals waiting for you with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties around the world? Keep this in mind the next time you're ready to check another destination off your must-visit list.
Why should I book my Middlebrook vacation package via Travelocity?
With exceptional service, 24/7 customer support and some of the most perfect escapes on offer, you'll never wander alone. And if you find a cheaper price, we'll match it. That's our Price Match Guarantee.
Can I save money on my Middlebrook car rental if I book it with a hotel or flight?
Combining your flight, car and hotel into a Middlebrook vacation package is a great way to score an amazing deal. Plus, having your own set of wheels gives you the freedom to find your way to all the landmarks you're eager to explore. Situated 40 mi from Middlebrook, Monticello is one attraction that should have a place on your itinerary. Fill up the tank and make a day trip of it.
Which airport is best for Middlebrook?
Charlottesville-Albemarle Airport (CHO) is 40 mi from the downtown area and is the beginning point for many unforgettable experiences. Alternatively, Lynchburg Regional Airport (LYH) is 50 mi away from central Middlebrook and Shenandoah Valley Regional Airport (SHD) is 25 mi away from central Middlebrook.
Where should I stay when visiting Middlebrook?
The Spacious Retreat on 34 Acres in the Country - Short Scenic Drive to Lexington! is recommended by many visitors. Book as soon as possible before it's too late.

Photos of local treasures

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You don't always have to go far from home to find something beautiful…Love living in the Shenandoah Valley! #goldenhour
You don't always have to go far from home to find something beautiful…Love living in the Shenandoah Valley! #goldenhour