Photo by Samantha Keyes

Middletown Hotels from S$97

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
22 Nov - 23 Nov
Tomorrow
23 Nov - 24 Nov
Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Middletown hotels

Breakfast area
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2.0 star property
Middletown
5.8 out of 10, (298)
"I loved staying here!"
United States
Whitney
The price is S$90
includes taxes & fees
4 Dec - 5 Dec
Econo Lodge Inn & Suites
Bar (on property)
Wayside Inn

Wayside Inn

3.5 star property
Middletown
9.2 out of 10, Wonderful, (414)
"Historic inn. "
United States
David
The price is S$172
includes taxes & fees
1 Dec - 2 Dec
Wayside Inn
2 restaurants, breakfast, lunch, dinner served; American cuisine
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, (1005)
"Love this hotel and the location. Staff is super friendly. "
United States
Casey
The price is S$188
includes taxes & fees
3 Dec - 4 Dec
The George Washington Hotel, A Wyndham Grand Hotel
Exterior
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, (1001)
"Excellent hotel. Rooms were clean, food was good. Staff was great. "
United States
Kathy
The price is S$129
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
Exterior
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, (2227)
"A run of the mill motel good for a travel break."
United States
CARL
The price is S$133
includes taxes & fees
17 Dec - 18 Dec
La Quinta Inn & Suites by Wyndham Winchester
Exterior
Hampton Inn & Suites Woodstock, VA

Hampton Inn & Suites Woodstock, VA

2.5 star property
Woodstock
8.8 out of 10, Excellent, (1003)
"Loved our stay"
United States
Tara
The price is S$133
includes taxes & fees
11 Dec - 12 Dec
Hampton Inn & Suites Woodstock, VA
Lift
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
Strasburg
8.2 out of 10, Very good, (1003)
"Friendly Staff, clean room."
Canada
Frank
The price is S$104
includes taxes & fees
23 Nov - 24 Nov
Ramada by Wyndham Strasburg/Shenandoah Valley
Snack bar
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (755)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is S$113
includes taxes & fees
3 Dec - 4 Dec
TRU By Hilton 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, (1000)
"The room was very clean and the staff were friendly and courteous."
United States
Maria
The price is S$111
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
Lobby
Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah

2.5 star property
Woodstock
8.8 out of 10, Excellent, (1006)
"The hotel was clean.and I had a comfortable stay."
United States
Monique
The price is S$137
includes taxes & fees
23 Nov - 24 Nov
Comfort Inn Woodstock Shenandoah
Lobby
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 star property
Winchester
8.6 out of 10, Excellent, (1090)
"Good price, good location "
United States
George
The price is S$97
includes taxes & fees
3 Dec - 4 Dec
Travelodge by Wyndham Winchester
Indoor pool
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

3.0 star property
Winchester
8.8 out of 10, Excellent, (505)
"Great hotel"
United States
DONNA D
The price is S$141
includes taxes & fees
30 Nov - 1 Dec
Hilton Garden Inn Winchester
1 bedroom, in-room safe, desk, laptop workspace
Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

2.5 star property
Winchester
8.8 out of 10, Excellent, (538)
"Very clean room, excellent staff!!!"
United States
James
The price is S$118
includes taxes & fees
23 Dec - 24 Dec
Candlewood Suites Winchester by IHG
Free buffet breakfast
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
Stephens City
8.2 out of 10, Very good, (797)
"Nice stay and friendly people "
United States
ALFRED
The price is S$113
includes taxes & fees
25 Nov - 26 Nov
Holiday Inn Express Winchester South-Stephens City by IHG
Exterior
Quality Inn Winchester

Quality Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1003)
"Staff are amazing stayed twice in a week and every one was so kind friendly and happy to have us The women who is in the breakfast room was super The rooms where clean and comfortable "
United States
Koren
The price is S$108
includes taxes & fees
15 Dec - 16 Dec
Quality Inn Winchester
Property entrance
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, (912)
"Great staff"
United States
Gordon
The price is S$80
includes taxes & fees
8 Dec - 9 Dec
Baymont by Wyndham Front Royal Near Shenandoah National Park
Bar (on property)
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, (1002)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is S$178
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Lobby
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1004)
"We thoroughly enjoyed all aspects of our stay, and look forward to the next time."
United States
Dennis
The price is S$144
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Front Royal
Lobby
Spark by Hilton Winchester

Spark by Hilton Winchester

3.0 star property
Winchester
9.0 out of 10, Wonderful, (1001)
"Great location close to restaurants "
United States
SILVIA
The price is S$121
includes taxes & fees
3 Dec - 4 Dec
Spark by Hilton Winchester
Exterior
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (794)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is S$132
includes taxes & fees
3 Dec - 4 Dec
Fairfield Inn & Suites 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.
View all properties

Black Friday Sale

Save up to 50% on select hotels
Book now
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 Battlefield Foundation

You can learn about the history of Middletown with a visit to Cedar Creek Battlefield Foundation. Stroll along the riverfront or experience the entertainment venues in this vibrant area.
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"As long as I don’t experience anything negative then my stay was great "
Howard 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Winchester, VA

More cheap stays in Middletown

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA
The price is S$97 per night from 3 Dec to 4 Dec
S$97
3 Dec - 4 Dec
includes taxes & fees
8.4/10 Very Good! (1,089 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. 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 Cedar Creek Battlefield Foundation and Belle Grove Plantation 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.

Explore a world of travel with Expedia