Photo by Samantha Keyes

Find hotels in Middletown, VA from ฿2,149

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
10 Jan - 11 Jan
Tomorrow
11 Jan - 12 Jan
Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Middletown hotels

Dining
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (419 reviews)
"Historic inn. "
United States
Anonymous traveller
The price is ฿2,259
฿2,805 total
includes taxes & fees
11 Jan - 12 Jan
Wayside Inn
Breakfast area
Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (299 reviews)
"I loved staying here!"
United States
Whitney
The price is ฿1,948
฿2,149 total
includes taxes & fees
20 Jan - 21 Jan
Econo Lodge Inn & Suites Middletown - Winchester South
Exterior
Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Holiday Inn Express Woodstock-Shenandoah Valley by IHG
2.5 star property
Woodstock
9.0 out of 10, Wonderful, (1,001 reviews)
"Great hotel I am always recommending the hotel."
United States
Salvatore
The price is ฿2,573
฿2,889 total
includes taxes & fees
18 Jan - 19 Jan
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
Lobby
Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah
2.5 star property
Woodstock
8.8 out of 10, Excellent, (1,002 reviews)
"Great place to stay. Clean, friendly and safe. Would stay again. "
United States
Beverly
The price is ฿2,795
฿3,139 total
includes taxes & fees
11 Jan - 12 Jan
Comfort Inn Woodstock Shenandoah
Free daily buffet breakfast
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2,244 reviews)
"Staff is very pleasant and personable. "
United States
Julie
The price is ฿2,880
฿3,133 total
includes taxes & fees
13 Jan - 14 Jan
La Quinta Inn & Suites by Wyndham Winchester
Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean rooms and property. Staff was amazing. Hot tub and pool area were great and clean. Very comfortable stay. Only issue was shower was very slow to drain but confident staff will fix it for next"
United States
Edward
The price is ฿3,061
฿3,377 total
includes taxes & fees
19 Jan - 20 Jan
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Snack bar
TRU By Hilton Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (784 reviews)
"Clean room, good breakfast, easy check in/out."
United States
Joseph
The price is ฿2,333
฿2,539 total
includes taxes & fees
26 Jan - 27 Jan
TRU By Hilton Winchester
Indoor pool
Hampton Inn Front Royal

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1,006 reviews)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is ฿3,061
฿3,407 total
includes taxes & fees
17 Jan - 18 Jan
Hampton Inn Front Royal
Exterior
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,092 reviews)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is ฿3,087
฿3,358 total
includes taxes & fees
8 Feb - 9 Feb
Comfort Inn & Suites Winchester
Exterior
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is ฿2,447
฿2,756 total
includes taxes & fees
18 Jan - 19 Jan
Holiday Inn Winchester Se-Historic Gateway by IHG
Lobby
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
Front Royal
7.6 out of 10, Good, (1,001 reviews)
"Good condition "
United States
Phillip
The price is ฿1,751
฿1,948 total
includes taxes & fees
13 Jan - 14 Jan
Super 8 by Wyndham Front Royal Near Shenandoah National Park
Lobby
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (813 reviews)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is ฿2,827
฿3,075 total
includes taxes & fees
19 Jan - 20 Jan
Fairfield Inn & Suites by Marriott Winchester
Property amenity
TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
Front Royal
9.6 out of 10, Exceptional, (558 reviews)
"Excellent staff, clean rooms, convenient location right next to grocery stores and restaurants. "
United States
Carla
The price is ฿3,451
฿3,869 total
includes taxes & fees
15 Jan - 16 Jan
TownePlace Suites by Marriott Front Royal
Bar (on property)
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,005 reviews)
"Great hotel!"
United States
CHARLES
The price is ฿3,973
฿4,502 total
includes taxes & fees
18 Jan - 19 Jan
The George Washington Hotel, A Wyndham Grand Hotel
Seasonal outdoor pool
Twi-Lite Inn

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very good, (544 reviews)
"Clean, comfortable room. Staff was nice and I really enjoyed my stay. Motel was in a high traffic area, but still a quiet stay"
United States
Daniel
The price is ฿2,133
฿2,374 total
includes taxes & fees
11 Jan - 12 Jan
Twi-Lite Inn
Winery
Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 star property
Front Royal
6.4 out of 10, (925 reviews)
"Staff was very kind! Had a nice time!"
United States
Rio Ashley
The price is ฿1,733
฿1,929 total
includes taxes & fees
18 Jan - 19 Jan
Baymont by Wyndham Front Royal Near Shenandoah National Park
Restaurant
Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (854 reviews)
"Clean room very nice staff"
United States
JEROME J
The price is ฿3,319
฿3,760 total
includes taxes & fees
16 Jan - 17 Jan
Hampton Inn Winchester N/Conference Center, VA
Lobby
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,004 reviews)
"Clean efficient room with good front desk service. Convienence to Highway 81 and eateries."
United States
Chris
The price is ฿2,647
฿2,879 total
includes taxes & fees
8 Feb - 9 Feb
Country Inn & Suites by Radisson, Winchester, VA
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Middletown attractions

Belle Grove Plantation

Find out about the history of Middletown when you spend time at Belle Grove Plantation. Wander the riverfront or discover the mountain views in this vibrant area.
See properties

Cedar Creek and Belle Grove National Historical Park

Explore the great outdoors at Cedar Creek and Belle Grove National Historical Park, a lovely green space in Middletown. Stroll along the riverfront or experience the area's entertainment venues.
See properties

Learn more about Middletown

History buffs can explore the Cedar Creek Battlefield and Belle Grove Plantation, where costumed interpreters bring Civil War stories to life. Visit the Wayside Inn, Virginia's oldest continuously operating inn, and ask locals about hidden hiking trails in nearby Shenandoah Valley.

See all hotels in Middletown
Nana’s Irish Pub was a great and delicious stop off the main road on the way to Asheville, NC. Super cute redesigned bank. The bank door is still in the corner and is not a closet. Highly suggested for a pit stop!
Photo by Samantha Keyes
Open Photo by Samantha Keyes

Top Middletown Hotel Reviews

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent
"Clean rooms and property. Staff was amazing. Hot tub and pool area were great and clean. Very comfortable stay. Only issue was shower was very slow to drain but confident staff will fix it for next"
Edward 1-night trip
Posted 11 days ago
DoubleTree by Hilton Front Royal Blue Ridge Shadows

More cheap stays in Middletown

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA
The price is ฿2,133 per night from 13 Jan to 14 Jan
฿2,133
฿2,321 total
13 Jan - 14 Jan
includes taxes & fees
8.4/10 Very Good! (1,083 reviews)

Frequently asked questions

Where is the best place for a stay in Middletown?
Wayside Inn is a favourite with Expedia customers. This hotel offers free parking and free WiFi. Another top choice for your trip based on traveller reviews is Econo Lodge Inn & Suites Middletown - Winchester South. See all available top hotels, or vacation rentals in Middletown.
If I need to cancel my hotel reservation in Middletown, will I receive a refund?
Yes, most hotel room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, you might be able to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Middletown.
What's it like staying in Middletown?
Visitors to Middletown will definitely enjoy the bars and restaurants. Tourists can also enjoy the city's entertainment choices, churches and theatres. In Middletown, there are 4 hotels and other accommodation options to choose from. Find out more about Middletown.
What is there to see in Middletown?
Landmarks like Belle Grove Plantation and Cedar Creek Battlefield Foundation might be worth a visit. The picturesque setting of Shenandoah River and Cedar Creek and Belle Grove National Historical Park exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Wayside Theater and Jackson's Chase Golf Course. Take a look at what more there is to see and do in Expedia's Middletown guide.
What's the seasonal weather like in Middletown?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Middletown is 1088 mm.