Middletown Hotels from ₹5,587

  • 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
23 Jan - 24 Jan
Tomorrow
24 Jan - 25 Jan
This weekend
23 Jan - 25 Jan
Next weekend
30 Jan - 1 Feb

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Middletown hotels

Dining

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (420 reviews)
"Historic inn. "
United States
Anonymous traveller
The price is ₹6,597
₹8,192 total
includes taxes & fees
26 Jan - 27 Jan
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, (300 reviews)
"I loved staying here!"
United States
Whitney
The price is ₹5,690
₹6,276 total
includes taxes & fees
1 Feb - 2 Feb
Econo Lodge Inn & Suites Middletown - Winchester South
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, (1,000 reviews)
"Great room and staff. Nice restaurant and bar also with good prices. Very nice hotel. 5 stars"
United States
Vincent
The price is ₹8,941
₹9,862 total
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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, (1,001 reviews)
"Great hotel I am always recommending the hotel."
United States
Salvatore
The price is ₹9,437
₹10,598 total
includes taxes & fees
27 Jan - 28 Jan
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
Lobby

Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah
2.5 star property
Woodstock
8.8 out of 10, Excellent, (1,002 reviews)
"The staff was helpful and the room was comfortable."
United States
Joseph
The price is ₹8,164
₹9,168 total
includes taxes & fees
25 Jan - 26 Jan
Comfort Inn Woodstock Shenandoah
Property amenity

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
Front Royal
9.6 out of 10, Exceptional, (561 reviews)
"Clean room, friendly and helpful staff, good breakfast, I would stay again."
United States
Catherine
The price is ₹10,079
₹11,300 total
includes taxes & fees
27 Jan - 28 Jan
TownePlace Suites by Marriott Front Royal
Exterior

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (96 reviews)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is ₹25,563
₹27,941 total
includes taxes & fees
18 Feb - 19 Feb
Glen Gordon Manor
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, (2,249 reviews)
"yes, room was spotless very nice place to stay"
United States
ROBERT
The price is ₹8,411
₹9,151 total
includes taxes & fees
25 Jan - 26 Jan
La Quinta Inn & Suites by Wyndham Winchester
Indoor pool

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1,002 reviews)
"Very nice breakfast (eggs sausage, potatoes, ...), clean lobby, and all the staff was friendly, including Beatrix. Also we appreciated the attention to a clean and warm pool room on a very cold January. Great mexican 1 mile away at Potrillo's."
United States
kenneth
The price is ₹8,941
₹9,951 total
includes taxes & fees
15 Feb - 16 Feb
Hampton Inn Front Royal
Bar (on property)

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, (1,005 reviews)
"Great hotel!"
United States
CHARLES
The price is ₹11,604
₹13,147 total
includes taxes & fees
1 Feb - 2 Feb
The George Washington Hotel, A Wyndham Grand Hotel
Exterior

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (799 reviews)
"Great stay!"
United States
Rene
The price is ₹9,813
₹10,676 total
includes taxes & fees
1 Feb - 2 Feb
SpringHill Suites by Marriott Winchester
Snack bar

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (789 reviews)
"Clean room, good breakfast, easy check in/out."
United States
Joseph
The price is ₹8,941
₹9,727 total
includes taxes & fees
1 Feb - 2 Feb
TRU By Hilton Winchester
Lobby

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (815 reviews)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is ₹8,489
₹9,236 total
includes taxes & fees
26 Jan - 27 Jan
Fairfield Inn & Suites by Marriott Winchester
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, (814 reviews)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is ₹6,780
₹7,377 total
includes taxes & fees
26 Jan - 27 Jan
Holiday Inn Express Winchester South-Stephens City by IHG
Interior

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (516 reviews)
"Great hotel"
United States
DONNA D
The price is ₹9,242
₹10,471 total
includes taxes & fees
30 Jan - 31 Jan
Hilton Garden Inn Winchester
Exterior

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,098 reviews)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is ₹8,968
₹9,757 total
includes taxes & fees
8 Feb - 9 Feb
Comfort Inn & Suites 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, (1,000 reviews)
"Great stay"
United States
Lori
The price is ₹7,513
₹8,450 total
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Winchester Se-Historic Gateway by IHG
Exterior

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (927 reviews)
"Room was great. Staff was extremely friendly."
United States
Amy
The price is ₹9,804
₹10,666 total
includes taxes & fees
30 Jan - 31 Jan
Courtyard by Marriott 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, (857 reviews)
"Super clean room comfy beds"
United States
Joy
The price is ₹9,692
₹10,981 total
includes taxes & fees
30 Jan - 31 Jan
Hampton Inn Winchester N/Conference Center, VA
Garden

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (175 reviews)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is ₹20,982
₹23,143 total
includes taxes & fees
27 Jan - 28 Jan
L'Auberge Provencale Inn & Restaurant
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
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

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
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Clean room. Friendly and helpful staff."
Richard 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester

More cheap stays in Middletown

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA
The price is ₹6,414 per night from 26 Jan to 27 Jan
₹6,414
₹6,978 total
26 Jan - 27 Jan
includes taxes & fees
8.4/10 Very Good! (1,070 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.
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.

Explore a world of travel with Expedia