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Middletown Hotels from ₹5,506

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8 Dec - 9 Dec
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9 Dec - 10 Dec
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12 Dec - 14 Dec
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19 Dec - 21 Dec

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Top 10 Middletown hotels and places to stay

Breakfast area
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2.0 star property
Middletown
5.8 out of 10, (299)
"I loved staying here!"
United States
Whitney
The price is ₹5,589
₹6,164 total
includes taxes & fees
16 Dec - 17 Dec
Econo Lodge Inn & Suites
Bar (on property)
Wayside Inn

Wayside Inn

3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"Historic inn. "
United States
David
The price is ₹6,479
₹8,046 total
includes taxes & fees
9 Dec - 10 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, (1012)
"Great hotel!"
United States
CHARLES
The price is ₹11,398
₹12,913 total
includes taxes & fees
14 Dec - 15 Dec
The George Washington Hotel, A Wyndham Grand Hotel
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, (2219)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is ₹9,404
₹10,232 total
includes taxes & fees
16 Dec - 17 Dec
La Quinta Inn & Suites by Wyndham Winchester
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)
"Rooms were clean. Pleasant and professional staff. Good breakfast."
United States
Lora
The price is ₹7,379
₹8,287 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
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, (1005)
"Clean room, nicely furnished."
United States
Marilyn
The price is ₹6,659
₹7,515 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
Snack bar
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (765)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is ₹6,551
₹7,128 total
includes taxes & fees
7 Jan - 8 Jan 2026
TRU By Hilton Winchester
Exterior
Hampton Inn & Suites Woodstock, VA

Hampton Inn & Suites Woodstock, VA

2.5 star property
Woodstock
8.8 out of 10, Excellent, (1001)
"Loved our stay"
United States
Tara
The price is ₹8,351
₹9,379 total
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn & Suites Woodstock, VA
Lobby
Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah

2.5 star property
Woodstock
8.8 out of 10, Excellent, (1004)
"Great place to stay. Clean, friendly and safe. Would stay again. "
United States
Beverly
The price is ₹8,323
₹9,346 total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Inn Woodstock Shenandoah
Lift
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
Strasburg
8.4 out of 10, Very good, (1006)
"Friendly Staff, clean room."
Canada
Frank
The price is ₹6,425
₹7,152 total
includes taxes & fees
1 Jan - 2 Jan 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
Exterior
Quality Inn Winchester

Quality Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1006)
"Great stay"
United States
Jaron
The price is ₹6,808
₹7,407 total
includes taxes & fees
15 Dec - 16 Dec
Quality Inn Winchester
Lobby
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 star property
Winchester
8.6 out of 10, Excellent, (1079)
"Good price, good location "
United States
George
The price is ₹6,119
₹6,658 total
includes taxes & fees
22 Dec - 23 Dec
Travelodge by Wyndham Winchester
Indoor pool
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

3.0 star property
Winchester
9.0 out of 10, Wonderful, (508)
"Great hotel"
United States
DONNA D
The price is ₹8,592
₹9,735 total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Winchester
Suite, 1 Bedroom | In-room safe, desk, laptop workspace, blackout curtains
Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

2.5 star property
Winchester
8.8 out of 10, Excellent, (542)
"Very clean room, excellent staff!!!"
United States
James
The price is ₹7,019
₹7,637 total
includes taxes & fees
3 Jan - 4 Jan 2026
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, (802)
"Nice stay and friendly people "
United States
ALFRED
The price is ₹6,659
₹7,245 total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Winchester South-Stephens City by IHG
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, (916)
"Staff was very kind! Had a nice time!"
United States
Rio Ashley
The price is ₹4,819
₹5,364 total
includes taxes & fees
23 Dec - 24 Dec
Baymont by Wyndham Front Royal Near Shenandoah National Park
Lobby
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1374)
"Excellent accommodations"
United States
Loretta
The price is ₹6,479
₹7,050 total
includes taxes & fees
5 Jan - 6 Jan 2026
Microtel Inn & Suites by Wyndham Winchester
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 ₹6,767
₹7,667 total
includes taxes & fees
4 Jan - 5 Jan 2026
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, (797)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is ₹8,338
₹9,072 total
includes taxes & fees
11 Dec - 12 Dec
Fairfield Inn & Suites by Marriott Winchester
Property amenity
Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG

2.5 star property
Winchester
9.0 out of 10, Wonderful, (798)
"Clean room, easy and quick check in."
United States
Jacqueline
The price is ₹9,359
₹10,183 total
includes taxes & fees
16 Dec - 17 Dec
Holiday Inn Express Hotel & Suites Winchester by IHG
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 Battlefield Foundation

The Cedar Creek Battlefield Foundation preserves this pivotal 1864 Civil War site through exhibits and trails. Experience history during October's annual reenactment featuring authentic battle scenarios.
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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Everything was great, including breakfast "
Kevin 1-night trip
Posted 2 days ago
Quality Inn Winchester

More cheap stays in Middletown

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA
The price is ₹6,119 per night from 22 Dec to 23 Dec
₹6,119
₹6,658 total
22 Dec - 23 Dec
includes taxes & fees
8.4/10 Very Good! (1,075 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 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.

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