Middletown Hotels from S$87

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Check prices for these dates

This weekend
22 May - 24 May
Next weekend
29 May - 31 May

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Our top choices for Middletown hotels

Dining

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (433 reviews)
"The history surrounding this place is fascinating. It was such a charming historic inn."
United States
Bethany
The price is S$184
includes taxes & fees
24 May - 25 May
Wayside Inn
Breakfast area

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (308 reviews)
"Clean rooms"
United States
Robbie
The price is S$96
includes taxes & fees
2 Jun - 3 Jun
Econo Lodge Inn & Suites Middletown - Winchester South
Lobby

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,005 reviews)
"Great location, clean rooms and friendly staff."
United States
Daniel
The price is S$120
includes taxes & fees
10 Jun - 11 Jun
Spark by Hilton Winchester
Exterior

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,002 reviews)
"Breakfast was great and we love that they let us bring small dogs"
United States
Claire VanWinkle
The price is S$117
includes taxes & fees
28 May - 29 May
Quality Inn Winchester
Lobby

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, (1,010 reviews)
"Location is right across the road from Spelunker's, the best casual restaurant in Virginia."
United States
Rachel
The price is S$104
includes taxes & fees
24 May - 25 May
Super 8 by Wyndham Front Royal Near Shenandoah National Park
Snack bar

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (876 reviews)
"Excellent hotel, great value!"
United States
Boris
The price is S$158
includes taxes & fees
14 Jun - 15 Jun
TRU By Hilton Winchester
Exterior

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,100 reviews)
"Very friendly front desk Quiet surroundings. Great restaurant nearby"
United States
Rosemary
The price is S$146
includes taxes & fees
21 Jun - 22 Jun
Comfort Inn & Suites Winchester
Lobby

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (859 reviews)
"great rooms!"
United States
Justine Patrick E.F.
The price is S$129
includes taxes & fees
7 Jun - 8 Jun
Fairfield Inn & Suites by Marriott Winchester
Porch

Relax Inn Motel

Relax Inn Motel
2.0 star property
Front Royal
8.2 out of 10, Very good, (275 reviews)
"The owners/managers are delightful. The room was very nice with excellent bedding. I look forward to staying there again "
United States
Sarah
The price is S$92
includes taxes & fees
24 May - 25 May
Relax Inn Motel
Lobby

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, (1,002 reviews)
"Staff are so nice and everything was good"
United States
Osama
The price is S$130
includes taxes & fees
15 Jun - 16 Jun
Country Inn & Suites by Radisson, Winchester, VA
Premium bedding, pillow-top beds, in-room safe, individually furnished

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, (893 reviews)
"Location was excellent"
United States
Jennie
The price is S$156
includes taxes & fees
2 Jun - 3 Jun
Hampton Inn Winchester N/Conference Center, VA
Lobby

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,077 reviews)
"always a great stay here... and walking distance from Shenandoah University."
United States
Faith
The price is S$99
includes taxes & fees
24 May - 25 May
Travelodge by Wyndham Winchester
Exterior

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (853 reviews)
"Great visit! "
United States
Susan
The price is S$158
includes taxes & fees
28 May - 29 May
SpringHill Suites by Marriott Winchester
Exterior

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, (1,001 reviews)
"Good for an overnight stay on our way up north."
United States
Cherilyn
The price is S$148
includes taxes & fees
24 May - 25 May
Holiday Inn Winchester Se-Historic Gateway by IHG
Lobby

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,458 reviews)
"This was my first stay at a Microtel and i was very impressed wirh the design and how well sound was controlled. I'll definitely stay again. "
United States
Carol
The price is S$131
includes taxes & fees
24 May - 25 May
Microtel Inn & Suites by Wyndham Winchester
Lobby

Motel 6 Front Royal, VA

Motel 6 Front Royal, VA
2.0 star property
Front Royal
7.0 out of 10, Good, (516 reviews)
"Good location, good value, helpful staff. Would use the facility again"
United States
Robert
The price is S$85
includes taxes & fees
26 May - 27 May
Motel 6 Front Royal, VA
Reception

Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
3.0 star property
Winchester
8.0 out of 10, Very good, (6 reviews)
"There was no shampoo nor shower gel and the shower was cool water. Takes 5 minutes to even get lukewarm water. No one at front desk to check out so ??? "
United States
Timothy
The price is S$156
includes taxes & fees
2 Jun - 3 Jun
Home2 Suites By Hilton Winchester
Free daily buffet breakfast

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, (2,269 reviews)
"Friendly staff, clean spacious rooms, plenty of parking and a great breakfast. We enjoyed our stay here for sure!!"
United States
Natalie
The price is S$168
includes taxes & fees
27 May - 28 May
La Quinta Inn & Suites by Wyndham Winchester
Lobby

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.2 out of 10, Very good, (1,006 reviews)
"Friendly staff and well maintained facilities. Great dog friendly property"
United States
Elaine
The price is S$120
includes taxes & fees
9 Jun - 10 Jun
Ramada by Wyndham Strasburg/Shenandoah Valley
Exterior

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (979 reviews)
"Beautiful hotel!"
United States
David
The price is S$149
includes taxes & fees
8 Jun - 9 Jun
Courtyard by Marriott Winchester
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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Stay near popular Middletown attractions

Belle Grove Plantation

4.2/5 (8 reviews)
This Jeffersonian-inspired Manor House showcases antebellum plantation life and Civil War history. Explore the heritage apple orchard and original outbuildings while enjoying panoramic mountain views.
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
Photo by Stephanie Sutton
Open Photo by Stephanie Sutton

Top Middletown Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

6/10 Okay
"The room was a little dirty, not wiped down enough, mirror was nasty, some.nasty stuff on bathroom wall"
Cain 1-night trip
Posted 4 hours ago
La Quinta Inn & Suites by Wyndham Winchester

More cheap stays in Middletown

APM Inn & Suites

APM Inn & Suites

1347 Berryville Ave Winchester VA
The price is S$87 per night from 17 Jun to 18 Jun
S$87
17 Jun - 18 Jun
includes taxes & fees
7/10 Good! (446 reviews)

Frequently asked questions

Where is the best place for a stay in Middletown?
Based on our traveller data, Wayside Inn is one of the top choices for your stay. This hotel offers free parking and free WiFi. Two other options for your visit to the area are Spark by Hilton Winchester and TRU By Hilton Winchester. 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 3 hotels and other accommodation options to choose from. Find out more about Middletown.
What is there to see in Middletown?
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 Belle Grove Plantation 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.

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