Middletown Hotels from โน6,798
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26 Aug - 27 AugTomorrow
27 Aug - 28 AugThis weekend
28 Aug - 30 AugNext weekend
4 Sept - 6 SeptOur top choices for Middletown hotels
1. Wayside Inn
Wayside InnMiddletown
Christine
โน11,593
โน13,740 total
includes taxes & fees
30 Aug - 31 Aug
2. Econo Lodge Inn & Suites Middletown - Winchester South
Econo Lodge Inn & Suites Middletown - Winchester SouthMiddletown
Nathan
โน6,164
โน6,798 total
includes taxes & fees
16 Sept - 17 Sept
3. Comfort Inn & Suites Winchester
Comfort Inn & Suites WinchesterWinchester
Richard
โน9,117
โน10,147 total
includes taxes & fees
30 Aug - 31 Aug
4. Fairfield Inn & Suites Strasburg Shenandoah Valley
Fairfield Inn & Suites Strasburg Shenandoah ValleyStrasburg
Patrick
โน11,240
โน12,510 total
includes taxes & fees
2 Sept - 3 Sept
5. Ramada by Wyndham Strasburg/Shenandoah Valley
Ramada by Wyndham Strasburg/Shenandoah ValleyStrasburg
Scott
โน6,894
โน7,673 total
includes taxes & fees
27 Aug - 28 Aug
6. Holiday Inn Express Winchester South-Stephens City by IHG
Holiday Inn Express Winchester South-Stephens City by IHGStephens City
Steven
โน8,396
โน9,345 total
includes taxes & fees
6 Sept - 7 Sept
7. Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VAWinchester
Phillip
โน9,011
โน10,029 total
includes taxes & fees
20 Sept - 21 Sept
8. La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham WinchesterWinchester
chouaib
โน9,789
โน10,896 total
includes taxes & fees
27 Aug - 28 Aug
9. Hampton Inn Front Royal
Hampton Inn Front RoyalFront Royal
Timothy
โน11,658
โน12,975 total
includes taxes & fees
2 Sept - 3 Sept
10. Quality Inn Stephens City - Winchester South
Quality Inn Stephens City - Winchester SouthStephens City
Nancy
โน8,072
โน8,984 total
includes taxes & fees
2 Sept - 3 Sept
11. TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front RoyalFront Royal
Justin
โน13,262
โน14,819 total
includes taxes & fees
17 Sept - 18 Sept
12. DoubleTree by Hilton Front Royal Blue Ridge Shadows
DoubleTree by Hilton Front Royal Blue Ridge ShadowsFront Royal
Adrian
โน11,658
โน12,858 total
includes taxes & fees
24 Sept - 25 Sept
13. Spark by Hilton Winchester
Spark by Hilton WinchesterWinchester
johnny
โน7,683
โน8,704 total
includes taxes & fees
17 Sept - 18 Sept
14. Fairfield Inn & Suites by Marriott Winchester
Fairfield Inn & Suites by Marriott WinchesterWinchester
Michael
โน8,840
โน9,839 total
includes taxes & fees
30 Aug - 31 Aug
15. Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHGWinchester
Jennifer
โน8,873
โน10,162 total
includes taxes & fees
30 Aug - 31 Aug
16. Microtel Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham WinchesterWinchester
Ricky
โน8,320
โน9,260 total
includes taxes & fees
30 Aug - 31 Aug
17. Holiday Inn Express Hotel & Suites Winchester by IHG
Holiday Inn Express Hotel & Suites Winchester by IHGWinchester
Susan
โน11,163
โน12,425 total
includes taxes & fees
30 Aug - 31 Aug
18. Courtyard by Marriott Winchester
Courtyard by Marriott WinchesterWinchester
Christine
โน10,219
โน11,373 total
includes taxes & fees
2 Sept - 3 Sept
19. Hampton Inn Winchester N/Conference Center, VA
Hampton Inn Winchester N/Conference Center, VAWinchester
Jackie
โน10,093
โน11,435 total
includes taxes & fees
6 Sept - 7 Sept
20. Comfort Inn Woodstock Shenandoah
Comfort Inn Woodstock ShenandoahWoodstock
Leah-Kate
โน9,030
โน10,141 total
includes taxes & fees
30 Aug - 31 Aug
Stay near popular Middletown attractions
Belle Grove Plantation
8.4/10 (8 reviews)
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.
Cedar Creek Battlefield Foundation
8.6/10 (7 reviews)
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.
Cedar Creek and Belle Grove National Historical Park
9.0/10 (6 reviews)
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.
Jackson's Chase Golf Course
6.0/10 (1 review)
This scenic 18-hole course weaves through the rolling Shenandoah Valley, challenging golfers of all abilities. Enjoy the serene natural setting while navigating its strategically designed par-72 layout.
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
Photo by Stephanie Sutton
Top Middletown Hotel Reviews
La Quinta Inn & Suites by Wyndham Winchester
8/10 Good
"Weโve stayed here numerous times due"
TRU By Hilton Winchester
10/10 Excellent
"The bedroom and bathroom were very clean!!"
Quality Inn Winchester
10/10 Excellent
"We were pleasantly surprised and very pleased with this property. We enjoyed our overnight stay and would definitely stay again. Convenient to I-81, yet surprisingly quiet"
Comfort Inn & Suites Winchester
10/10 Excellent
"Clean room ,quiet,plenty to parking"
Holiday Inn Winchester Se-Historic Gateway by IHG
10/10 Excellent
"Staff great"
Fairfield Inn & Suites by Marriott Winchester
10/10 Excellent
"Very clean"
Hampton Inn & Suites Woodstock, VA
10/10 Excellent
"."
Microtel Inn & Suites by Wyndham Winchester
8/10 Good
"The property was clean! The rooms were comfortable and clean. Didn't like the small hard bed pillows! And when there's two people in the room, I wish they would provide two packets of regular coffee. Not one regular coffee and one decaf."
Spark by Hilton Winchester
8/10 Good
"The hotel and room were the cleanest place I have stayed at in a long time! Definitely would recommend it to anyone."
More cheap stays in Middletown
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
โน6,583
โน7,262 total
27 Aug - 28 Aug
includes taxes & fees
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
โน6,894
โน7,673 total
27 Aug - 28 Aug
includes taxes & fees
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
โน8,029
โน8,936 total
2 Sept - 3 Sept
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
โน8,320
โน9,260 total
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (1,458 reviews)
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
โน9,117
โน10,147 total
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (1,139 reviews)
Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
โน11,658
โน12,975 total
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (1,022 reviews)
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