Middletown Virginia Hotels & Motels

Only hotels in Middletown are listed below. Find cheap and discounted hotel/motel rates in or nearby Middletown, VA for your upcoming personal or group travel. Discover the most favored Middletown, Virginia hotel and motel rooms. Browse the Middletown area hotels to find the perfect lodging! Please use the provided map of the Middletown hotels. Group booking? Search Middletown Group Hotel Rates

The Middletown center is about 4 miles southwest of The Family Drive In and 11 miles southwest of Abram's Delight Museum.

Witness the allure of Middletown, Virginia, a quaint, historic destination in the beautiful Shenandoah Valley. A visit to Middletown is like stepping back in time, where heritage buildings and the rich local past weave a fascinating tale that captivates all who wander its scenic streets. For history buffs, Middletown's well-preserved Civil War sites offer an immersive glimpse into the past. Nature lovers will delight in the town's spectacular trails, perfect for hiking and biking, while the nearby Shenandoah River beckons for an afternoon of fishing or canoeing. Middletown's vivid community hosts festivals and events annually, showing visitors a taste of local culture, arts, and entertainment. Foodies can indulge in the delightful array of dining options, from farm-to-table eateries to local wine tastings, ensuring a culinary journey that satisfies every palate. When it comes to accommodations, Middletown houses a vast range of options. From lovely bed and breakfasts to modern hotels, there's a place to rest for every type of traveler. Each establishment provides a warm, welcoming atmosphere, ensuring your trip is as enjoyable as the town itself. Explore this Virginia destination where culture, nature, and hospitality merge to create an unforgettable travel experience. More from this guide...

Middletown Hotels & Accommodations

Econo Lodge Inn & Suites Middletown - Winchester South - Middletown 91 Reliance Rd., Middletown, VA 22645 Call
  • Cheap property
  • Check-in: 11:00
From$49
Poor 2.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites Strasburg Shenandoah Valley - Strasburg 33760 Old Valley Pike, Strasburg, VA 22657 Call ~3.58 miles west of Middletown
  • 3 star Rural property
  • 4 floors in property
From$104
Very Good 4.0 /5 Reviews Call BookMore Details
Ramada by Wyndham Strasburg 21 Signal Knob Dr., Strasburg, VA 22657 Call ~3.85 miles west of Middletown
  • 2 star Rural hotel
  • 2 conference rooms in property
From$63
Average 3.0 /5 Latest Reviews Call BookMore Details
Quality Inn Stephens City - Winchester South : 167 Town Run Lane 167 Town Run Lane, Stephens City, VA 22655 Call ~5.03 miles northeast of Middletown
  • Three Star Highway property
  • Check-in: 3:00pm
From$60
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express - Stephens City 165 Town Run Ln, Stephens City, VA 22655 Call ~5.03 miles northeast of Middletown
  • Midscale Rural property
  • 3 floors in property
From$68
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hotel Strasburg - Strasburg 213 South Holliday St., Strasburg, VA 22657 Call ~5.16 miles southwest of Middletown
  • Affordable Mountain property
  • 8 suites in property
From$40
Average 3.5 /5 Reviews Call BookMore Details
Doubletree by Hilton Front Royal Blue Ridge Shadows 111 Hospitality Dr., Front Royal, VA 22630 Call ~5.99 miles east of Middletown
  • 3-star Golf Course property
  • 124 rooms in property
From$80
Very Good 4.0 /5 Reviews Call BookMore Details
Towneplace Stes Front Marriott - Front Royal 85 Caroline Dr., Front Royal, VA 22630 Call ~6.59 miles southeast of Middletown
  • Midscale hotel
  • 84 suites in property
From$90
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn Front Royal 9800 Winchester Rd., Front Royal, VA 22630 Call ~6.62 miles southeast of Middletown
  • 3 star Suburban hotel
  • Check-in: 03:00 PM
From$107
Very Good 4.0 /5 Review Score Call BookMore Details
Motel 6 Front Royal, VA 141 West 15th St., Front Royal, VA 22630 Call ~7.68 miles southeast of Middletown
  • Economy property
From$60
Average 3.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites Winchester in Winchester 195 Kernstown Commons Blvd., Winchester, VA 22602 Website Call ~7.83 miles northeast of Middletown
  • Inexpensive Suburban hotel
  • Access to gym on-site
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Country Inn & Suites : 141 Kernstown Commons Blvd. 141 Kernstown Commons Blvd., Winchester, VA 22602 Call ~7.92 miles northeast of Middletown
  • 3 star Suburban property
  • Check-in time: 3:00 pm
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Baymont by Wyndham Front Royal Near Shenandoah National Park in Front Royal 10 South Commerce Ave., Front Royal, VA 22630 Call ~9.18 miles southeast of Middletown
  • Two star Suburban hotel
  • Check-in: 3:00 PM
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Super 8 by Wyndham Front Royal Near Shenandoah National Park 111 South St., Front Royal, VA 22630 Call ~9.29 miles southeast of Middletown
  • 2 star Mountain hotel
  • Check in time: 2.00 Pm
From$60
Average 3.0 /5 Latest Reviews Call BookMore Details
Motel 6 Winchester Va 2951 Valley Ave., Winchester, VA 22601 Call ~9.56 miles northeast of Middletown
  • 2-star Suburban property
  • 67 rooms in property
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Home2 Suites Ny Hilton Winchester Trex Wy Winchester, Winchester, VA 22601 Call ~10.42 miles northeast of Middletown
  • 3-star Highway hotel
  • Comp. Breakfast
From$80
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Winchester Se-Historic Gateway by IHG 333 Front Royal Pike, Winchester, VA 22602 Call ~10.93 miles northeast of Middletown
  • Midscale Suburban property
  • 130 sleeping rooms in hotel
From$69
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Sleep Inn & Suites Winchester Near University : 140 Costello Dr. 140 Costello Dr., Winchester, VA 22602 Call ~11.08 miles northeast of Middletown
  • Two star Suburban hotel
  • Hotel has 4 floors
From$60
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Fairfield & Suites by Marriott Winchester 250 Front Royal Pike, Winchester, VA 22601 Call ~11.10 miles northeast of Middletown
  • Midscale Rural property
  • 3 floors in hotel
From$70
Very Good 4.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites by Marriott : 250 Front Royal Pike 250 Front Royal Pike, Winchester, VA 22602 Call ~11.10 miles northeast of Middletown
  • 3-star Suburban hotel
  • Check in: 4:00 PM
From$85
Average 3.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Winchester - Winchester 120 Wingate Dr., Winchester, VA 22601 Call ~11.30 miles northeast of Middletown
  • 3 star Highway hotel
  • 5 floors in property
From$90
Very Good 4.5 /5 Read Reviews Call BookMore Details
Travelodge by Wyndham Winchester in Winchester 160 Front Royal Pike, Winchester, VA 22602 Call ~11.33 miles northeast of Middletown
  • Economy Suburban hotel
  • 8 suites in hotel
From$49
Average 3.0 /5 Guest Reviews Call BookMore Details
Clarion Inn & Conference Center in Winchester 711 Millwood Ave., Winchester, VA 22601 Call ~11.42 miles northeast of Middletown
  • Low priced Highway hotel
  • 4 conference rooms in property
From$55
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Red Roof Inn Winchester, VA : 991 Millwood Pike 991 Millwood Pike, Winchester, VA 22602 Call ~11.43 miles northeast of Middletown
  • Two-star Suburban property
  • 2 floors in hotel
From$47
Average 3.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Winchester University / Mall Area 640 East Jubal Early Dr., Winchester, VA 22601 Call ~11.44 miles northeast of Middletown
  • Three Star Highway property
  • Hotel has an eco-friendly policy See policy
From$82
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Super 8 by Wyndham Winchester VA - Winchester 1077 Millwood Pike, Winchester, VA 22602 Call ~11.48 miles northeast of Middletown
  • Low-priced hotel
From$60
Average 3.0 /5 Guest Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Winchester : 1055 Millwood Pike 1055 Millwood Pike, Winchester, VA 22602 Call ~11.48 miles northeast of Middletown
  • Three Star Suburban property
  • Check in: 03:00PM
From$80
Very Good 4.0 /5 Read Reviews Call BookMore Details
Courtyard by Marriott Winchester 300 Marriott Dr., Winchester, VA 22603 Call ~12.17 miles north of Middletown
  • Three Star Suburban property
  • Check in: 3:00 PM
From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn & Suites in Winchester 30 Wolfe St. Apt 2e, Winchester, VA 22601 Call ~12.36 miles northeast of Middletown
  • Low-priced hotel
From$60
Average 3.0 /5 Latest Reviews Call BookMore Details
Microtel Inn & Suites by Wyndham Winchester 150 Faraday Plaza, Winchester, VA 22603 Call ~12.60 miles northeast of Middletown
  • Cheap Highway property
  • Check-in time: 3:00 PM
From$60
Average 3.0 /5 Reviews Call BookMore Details
The George Washington a Wyndham Grand Hotel - Winchester 103 East Piccadilly St., Winchester, VA 22601 Call ~12.62 miles northeast of Middletown
  • Affordable Downtown hotel
  • Check in: 4:00pm
From$99
Very Good 4.0 /5 Read Reviews Call BookMore Details
Apm Inn & Suites - Winchester 1347 Berryville Ave., Winchester, VA 22601 Call ~13.20 miles northeast of Middletown
  • Inexpensive property
  • Check in: 3:00 PM
From$50
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Winchester N/Conference Center, VA - Winchester 1204 Berryville Ave., Winchester, VA 22601 Call ~13.29 miles northeast of Middletown
  • Affordable Highway hotel
  • Free comp. breakfast
From$84
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Towneplace Suites by Marriott Winchester 170 Getty Ln, Winchester, VA 22603 Call ~13.66 miles northeast of Middletown
  • Affordable Suburban property
  • Hotel has 104 suites
From$74
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites : 142 Fox Ridge Lane 142 Fox Ridge Lane, Winchester, VA 22603 Call ~14.75 miles northeast of Middletown
  • 3-star Rural property
  • 81 sleeping rooms in hotel
From$75
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Quality Inn Winchester 1601 Martinsburg Pike, Winchester, VA 22603 Website Call ~14.97 miles northeast of Middletown
  • 2 star Highway hotel
  • Hotel has 2 floors
From$77
Very Good 4.0 /5 Review Score Call BookMore Details
Days Inn by Wyndham Winchester in Winchester 1593 Martinsburg Pike, Winchester, VA 22603 Call ~15.09 miles northeast of Middletown
  • Cheap Highway hotel
From$45
Average 3.5 /5 Recent Reviews Call BookMore Details
TRU by Hilton Winchester 118 Mercedes Court, Winchester, VA 22603 Call ~15.15 miles northeast of Middletown
  • 3 star property
  • Check in time: 15:00
From$90
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Springhill Suites Winchester : 280 Market St. 280 Market St., Winchester, VA 22603 Call ~15.62 miles northeast of Middletown
  • 3 star Suburban property
  • Fitness + Health Center
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Springhill Suites by Marriott Winchester 280 Maket St., Winchester, VA 22603 Call ~15.62 miles northeast of Middletown
  • Affordable hotel
From$90
Very Good 4.0 /5 Review Score Call BookMore Details
Comfort Inn Woodstock Shenandoah in Woodstock 1011 Motel Dr., Woodstock, VA 22664 Website Call ~16.87 miles southwest of Middletown
  • Low priced Highway property
  • Gym / Fitness Center Available
From$81
Very Good 4.5 /5 Reviews Call BookMore Details
Comfort Inn Woodstock Shenandoah in Woodstock 1101 Motel Dr., Woodstock, VA 22664 Call ~16.98 miles southwest of Middletown
  • Low-priced Highway property
  • 2 suites in hotel
From$89
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Woodstock-Shenandoah Valley by IHG : 1130 Motel Dr. 1130 Motel Dr., Woodstock, VA 22664 Call ~17.02 miles southwest of Middletown
  • Affordable Highway hotel
  • Check-in: 3:00pm
From$70
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites 1150 Motel Dr., Woodstock, VA 22664 Call ~17.23 miles southwest of Middletown
  • Midscale Highway hotel
  • 30 suites in hotel
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Econo Lodge Woodstock - Shenandoah Valley I-81 1290 South Main St., Woodstock, VA 22664 Call ~17.52 miles southwest of Middletown
  • Two-star Highway property
  • 40 sleeping rooms in hotel
From$50
Average 3.0 /5 Recent Reviews Call BookMore Details
Days Inn by Wyndham Luray Shenandoah in Luray 138 Whispering Hill Rd., Luray, VA 22835 Call ~25.36 miles south of Middletown
  • Low Cost Mountain property
  • Hotel has 100 rooms
From$107
Average 3.0 /5 Read Reviews Call BookMore Details
Motel 6 Mount Jackson Va Shenandoah 250 Conicville Rd., Mount Jackson, VA 22842 Call ~26.23 miles southwest of Middletown
  • Cheap Mountain property
  • Hotel has 100 rooms
From$55
Average 3.5 /5 Guest Reviews Call BookMore Details
Hampton Inn Martinsburg South-Inwood - Inwood 4758 Gerrardstown Rd., Inwood, WV 25428 Call ~26.30 miles northeast of Middletown
  • Mid-scale Rural hotel
  • Hotel has a green policy See policy
From$89
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Quality Inn Luray 410 West Main St., Luray, VA 22835 Call ~26.86 miles south of Middletown
  • Mid-scale Downtown hotel
  • Check in: 11:00
From$69
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Big Meadows Lodge : Skyline Dr. Mile 51 Skyline Dr. Mile 51, Shenandoah Natl Park, VA 22835 Call ~27.11 miles south of Middletown
  • 3-star hotel
  • Check in: 15:00
From$90
Very Good 4.0 /5 Latest Reviews Call BookMore Details

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Plan Your Trip to Middletown, VA and Enjoy the Best Time to Visit

Brimming with character, Middletown, Virginia is a destination that features something distinctive every season. As you plan your getaway, it's essential to consider what kind of activities you want to engage in and how the weather might affect them. Middletown is located in a region with a humid subtropical climate. This means it experiences various weather conditions throughout the year, from hot, humid summers to cool winters punctuated by moderate snowfall. Understanding this climatic pattern can help you plan your trip accordingly, ensuring you make the most of what Middletown offers. During summer months, specifically from June to September, Middletown basks in the season's warmth. The average high temperature in July floats around a balmy 86.9 °F, making it ideal for outdoor pastimes. The town comes alive during this period with a host of warm-weather pursuits, from hiking and biking in the scenic Shenandoah Valley to exploring the local farmer's markets and vineyards. It is the most popular time to visit the destination, with travelers flocking to soak up the sun and admire the stunning scenery. Despite their cooler temperatures, the winter months bring their allure to the town. January sees low temperatures of around 22.9 °F, with an average of 23.2 inches of snowfall annually. The area receives a fair amount of rainfall, with an annual average precipitation of 40.2 inches. While this might mean packing an extra umbrella or raincoat, it also contributes to the lush greenery and vivid flora that make Middletown a picturesque place. Whenever you choose to visit, Middletown, with its storied past, diverse attractions, and welcoming community, will leave you with memories to last a lifetime. So, whether you're setting off on a summer adventure or a winter escapade, Middletown, Virginia, awaits to welcome you with open arms.

Big Savings on Hotels in Middletown, VA - Don't Miss Out

Planning a trip to Middletown, VA? Turn to HotelPlanner for the best deals and savings. HotelPlanner offers great price reductions on accommodation bookings for both solo travelers and groups. This is due to ongoing collaborations with various hotels in and around Middletown, facilitating discounted rates that are easy on the wallet. Special rates are also available for military personnel, veterans, and senior citizens, helping these groups save significantly on their stays. The savings don't stop in Middletown. HotelPlanner also extends its great deals to nearby areas, opening up more possibilities for your trip. So, whether you're exploring Middletown's unique offerings, or venturing into nearby localities, let HotelPlanner provide you with a comfortable and affordable stay.

Middletown, VA - Home of History and Natural Beauty

From its picturesque landscapes to its rich past, Middletown presents a perfect blend of old-world and modern-day amenities, making it a must-visit destination. Founded in 1796, its roots trace back to the late 18th century, with German settlers Dr. Peter Senseney and his wife Magdelen making it their home. Originally known as "Senseney Town", Middletown was a piece of land within the 17th Century Fairfax Grant, gifted to allies who sided with England during the civil war. This captivating history is woven throughout the region and can be discovered in well-preserved architecture and historic sites. Just a mile southwest of Middletown, you'll find Belle Grove Plantation, which was first settled around 1750. This plantation's manor house, a hallmark of Federal-style architecture, was completed in 1797 and offers a glimpse into the town's historic legacy. Middletown also holds a significant place in the Civil War narrative, most notably with the Battle of Cedar Creek that played out just to the south. Today, this battlefield is part of the Cedar Creek and Belle Grove National Historical Park. The town takes pride in its Wayside Inn, which is held to be the longest-operating inn in the country, further underscoring Middletown's rich history. Visitors can also explore other historical landmarks such as Fort Bowman, Monte Vista, and St. Thomas Chapel. Middletown's location affords breathtaking views and easy access to surrounding cities. The town lies on a beautiful ridge between Meadow Brook and the tributaries of Molly Booth Run. Its proximity to major transportation routes like US Route 11 and Interstate 81 makes it easily accessible for visitors, with direct links to states like West Virginia, Pennsylvania, Maryland, New York, and Tennessee. The destination's appeal doesn't stop at its past and location; it also boasts an array of recreational facilities. The Middletown Community Park offers an excellent space for outdoor activities. At the same time, the Cedar Creek and Belle Grove National Historical Park provide a fascinating exploration of the area's Civil War period. The Family Drive-In Theatre offers a nostalgic movie-watching experience, and Cousins Paintball Skyline presents an adrenaline-filled activity for the adventurous. So, pack your bags and start planning your trip to Middletown, Virginia where history and modern amenities await you.

What did travelers think of the city of Middletown?

Below are reviews of the city of Middletown, VA from an actual visitor's perspective.

"Vault and Cellar restaurant was terrific"
Score 4.0 / 5

Andrew H., from 12-Sep-2025
"Peaceful Small Town With Good Italian Restaurant!"
Score 4.0 / 5

Small town, quiet and peaceful. Good food at Italian Touch restaurant!

Miranda W., from 01-Apr-2025
"Beautiful Scenery!"
Score 5.0 / 5

Small roads, very old homes lining the roads. Mountain and valley scenery.

Suzanne C., from 28-Sep-2022
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