Photo by Samantha Keyes

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7 Dec - 8 Dec
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8 Dec - 9 Dec
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12 Dec - 14 Dec
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Top hotels and accommodation in Middletown

Breakfast area
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2.0 star property
Middletown
5.8 out of 10, (299)
"Super nice reception, and the room was spartan but very clean and correct."
United States
Roger
The price is AU$103
includes taxes & fees
14 Dec - 15 Dec
Econo Lodge Inn & Suites
Bar (on property)
Wayside Inn

Wayside Inn

3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"The room was very clean"
United States
Marina
Travelling with partner
The price is AU$135
includes taxes & fees
8 Dec - 9 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, (1009)
"Very clean and a great location, walking distance to shopping and restaurants."
United States
Kathryn
Travelling with family
The price is AU$216
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, (2217)
"the room was super clean and modern"
United States
Jordan
Travelling for leisure
The price is AU$171
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)
"The room was clean and comfortable"
United States
Glenn
Travelling for business
The price is AU$139
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, (1004)
"Comfy beds, nice shower, and we had a view of the local airfield."
United States
Kenna
Travelling with family
The price is AU$126
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
Exterior
Hampton Inn & Suites Woodstock, VA

Hampton Inn & Suites Woodstock, VA

2.5 star property
Woodstock
8.8 out of 10, Excellent, (1001)
"The pool and hot tub were impeccably clean and well kept."
United States
Laura
Travelling with partner
The price is AU$158
includes taxes & fees
30 Dec - 31 Dec
Hampton Inn & Suites Woodstock, VA
Snack bar
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (765)
"Very comfortable beds and a large bathroom"
United States
Stephens
Travelling solo
The price is AU$119
includes taxes & fees
7 Jan - 8 Jan 2026
TRU By Hilton Winchester
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, (1005)
"The hotel was very clean."
United States
Kelley
Travelling with friends
The price is AU$120
includes taxes & fees
23 Dec - 24 Dec
Ramada by Wyndham Strasburg/Shenandoah Valley
Lobby
Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah

2.5 star property
Woodstock
8.8 out of 10, Excellent, (1004)
"The beds are very clean and comfortable."
United States
Xiaoling
The price is AU$159
includes taxes & fees
6 Jan - 7 Jan 2026
Comfort Inn Woodstock Shenandoah
Lobby
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 star property
Winchester
8.6 out of 10, Excellent, (1078)
"Nothing fancy, but it was clean, and the beds were very comfortable."
United States
John
Travelling for leisure
The price is AU$111
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)
"Friendly staff and clean room."
United States
Jennie
Travelling for leisure
The price is AU$163
includes taxes & fees
14 Dec - 15 Dec
Hilton Garden Inn Winchester
Exterior
Quality Inn Winchester

Quality Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1006)
"The room was spacious, quiet, well-appointed, and well maintained."
United States
Chris
Travelling solo
The price is AU$124
includes taxes & fees
14 Dec - 15 Dec
Quality Inn Winchester
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 room, very comfortable bed."
United States
Earl
Travelling for leisure
The price is AU$121
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Winchester South-Stephens City by IHG
Suite, 1 Bedroom
Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

2.5 star property
Winchester
8.8 out of 10, Excellent, (542)
"looked online and found a great mexican restaurant within a couple of miles"
United States
Victor K
Travelling with partner
The price is AU$128
includes taxes & fees
3 Jan - 4 Jan 2026
Candlewood Suites Winchester 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)
"Linens were very nice especially the towels."
United States
Angela
Travelling with family
The price is AU$90
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)
"Nice property, quiet location and very clean rooms!"
United States
Aimee
The price is AU$118
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)
"The shower is beautiful !"
United States
Takia
Travelling for leisure
The price is AU$128
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)
"Room was clean and a quiet area"
United States
Renee
Travelling with family
The price is AU$152
includes taxes & fees
11 Dec - 12 Dec
Fairfield Inn & Suites by Marriott Winchester
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, (1000)
"The hotel had everything I needed and the hot tub/pool were excellent."
United States
Stephen
Travelling for leisure
The price is AU$167
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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

Recent Reviews in Middletown

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Très très bien déjeuné wow depuis 20 ans que je passe par la ils s'améliore toujours "
roger 1-night trip
Posted 3 days ago
Travelodge by Wyndham Winchester

More cheap accommodation in Middletown

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA
The price is AU$111 per night from 22 Dec to 23 Dec
AU$111
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.
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. 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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