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Check prices for these dates

Tonight
24 Mar - 25 Mar
Tomorrow
25 Mar - 26 Mar
This weekend
27 Mar - 29 Mar
Next weekend
3 Apr - 5 Apr

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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, (426 reviews)
"Old building but clean and very comfortable. Perfect spot and price."
United States
Caroline
The price is NZ$153
includes taxes & fees
30 Mar - 31 Mar
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, (303 reviews)
"I loved staying here!"
United States
Whitney
The price is NZ$117
includes taxes & fees
21 Apr - 22 Apr
Econo Lodge Inn & Suites Middletown - Winchester South
Lobby

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (829 reviews)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is NZ$172
includes taxes & fees
29 Mar - 30 Mar
Fairfield Inn & Suites by Marriott 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, (2,279 reviews)
"Great hotel stay for our trip down soutg! Very clean and very nice rooms- very quiet!"
United States
Nancy
The price is NZ$199
includes taxes & fees
26 Mar - 27 Mar
La Quinta Inn & Suites by Wyndham Winchester
Exterior

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,093 reviews)
"Very clean, friendly staff, ample parking. Full breakfast included. Walkable to shopping and dining options. "
United States
Eileen
The price is NZ$190
includes taxes & fees
22 Apr - 23 Apr
Comfort Inn & Suites 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, (1,000 reviews)
"The national park was close by. That’s why we chose this location. That’s the only positive thing I can say. The rooms weren’t clean. The bathroom was disgusting. I stay in a lot of places to simply shower and sleep, but I wouldn’t stay here again. "
United States
Alayna
The price is NZ$116
includes taxes & fees
29 Mar - 30 Mar
Super 8 by Wyndham Front Royal Near Shenandoah National Park
Reception

Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
3.0 star property
Winchester
The price is NZ$189
includes taxes & fees
19 Apr - 20 Apr
Home2 Suites By Hilton Winchester
Restaurant

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, (870 reviews)
"The staff was wonderful! "
United States
Jayne
The price is NZ$204
includes taxes & fees
30 Mar - 31 Mar
Hampton Inn Winchester N/Conference Center, VA
Standard Double Room, 2 Double Beds, Non Smoking

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,004 reviews)
"Everything was perfect. Would highly recommend this hotel"
Canada
Phyllis
The price is NZ$164
includes taxes & fees
30 Mar - 31 Mar
Quality Inn Winchester
Exterior

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (826 reviews)
"Beautiful hotel and room. Accessible room was perfect. Staff was friendly right from check-in. Would highly recommend this hotel to anyone who needs an accessible room. "
United States
Andrew
The price is NZ$211
includes taxes & fees
30 Mar - 31 Mar
SpringHill Suites by Marriott Winchester
Lobby

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,451 reviews)
"Everything,room was amazing, staff so friendly, breakfast very good "
United States
Douglas Gary
The price is NZ$162
includes taxes & fees
26 Mar - 27 Mar
Microtel Inn & Suites by Wyndham 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, (1,005 reviews)
"very nice hotel,very clean"
Canada
Maria
The price is NZ$151
includes taxes & fees
5 Apr - 6 Apr
Holiday Inn Winchester Se-Historic Gateway by IHG
Exterior

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, (839 reviews)
"Yes. Parking was great"
United States
John
The price is NZ$163
includes taxes & fees
29 Mar - 30 Mar
Holiday Inn Express Winchester South-Stephens City by IHG
Lobby

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,003 reviews)
"Clean and excellent staff!"
United States
Diane
The price is NZ$173
includes taxes & fees
30 Mar - 31 Mar
Spark by Hilton Winchester
Reception

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (493 reviews)
"Great place to rest. Clean and family/pet friendly. "
United States
Noe
The price is NZ$210
includes taxes & fees
26 Mar - 27 Mar
TownePlace Suites by Marriott Winchester
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, (1,004 reviews)
"Very clean rooms and friendly staff."
United States
Christine
The price is NZ$169
includes taxes & fees
14 Apr - 15 Apr
Country Inn & Suites by Radisson, Winchester, VA
Lobby lounge

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
Strasburg
9.0 out of 10, Wonderful, (1,000 reviews)
"Asked for quiet floor after a long week of travels for work and he put me on the 4th floor Was super quiet , super clean and breakfast was decent,"
United States
angie
The price is NZ$215
includes taxes & fees
7 Apr - 8 Apr
Fairfield Inn & Suites Strasburg Shenandoah Valley
Indoor pool

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1,004 reviews)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is NZ$194
includes taxes & fees
12 Apr - 13 Apr
Hampton Inn Front Royal
Seasonal outdoor pool

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very good, (548 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 NZ$137
includes taxes & fees
29 Mar - 30 Mar
Twi-Lite Inn
Lobby

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,074 reviews)
"Very clean and great rates will stay again if in the area "
United States
Cindi
The price is NZ$125
includes taxes & fees
27 Mar - 28 Mar
Travelodge by Wyndham 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

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

Cedar Creek and Belle Grove National Historical Park

Explore the pivotal Civil War battlefield where Union forces secured the Shenandoah Valley in 1864. Tour the elegant Belle Grove Manor House and follow interpretive trails detailing strategic troop movements.
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
Beautiful drive up to this plantation. You can take a tour of it as well.
Photo by Stephanie Sutton
Open Photo by Stephanie Sutton

Top Middletown Hotel Reviews

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

6/10 Okay
"Convenient location. The pool is clean and fitness facility is quite good. Breakfast is excellent and in good service."
Tong 1-night trip
Posted 10 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

More cheap accommodation in Middletown

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA
The price is NZ$125 per night from 27 Mar to 28 Mar
NZ$125
27 Mar - 28 Mar
includes taxes & fees
8.6/10 Excellent! (1,074 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.
What are some of the best holiday rentals that Middletown has to offer?
Secluded River Cabin Getaway (Masten Cabin): This holiday home rental outside of Middletown is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. See all 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. Additionally, you might want to add Jackson's Chase Golf Course to your itinerary. 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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