𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Middletown (2026)

A large house in a field with a cloudy sky.

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Go beyond your typical stay in Middletown

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Our top choices for Middletown hotels

Breakfast included

Pet friendly

Hotel

Reserve now, pay later

Motel

Breakfast, lunch, dinner and brunch served

1. Wayside Inn

Middletown

Christine

S$183

includes taxes & fees

14 Sept - 15 Sept

Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

2. Econo Lodge Inn & Suites Middletown - Winchester South

Middletown

Nathan

S$91

includes taxes & fees

10 Sept - 11 Sept

3. Fairfield Inn & Suites Strasburg Shenandoah Valley

Strasburg

Patrick

S$160

includes taxes & fees

7 Sept - 8 Sept

4. Ramada by Wyndham Strasburg/Shenandoah Valley

Strasburg

Mantu

S$102

includes taxes & fees

30 Aug - 31 Aug

Desk, blackout curtains, iron/ironing board, free WiFi

5. Comfort Inn & Suites Winchester

Winchester

Richard

S$140

includes taxes & fees

10 Sept - 11 Sept

Desk, laptop workspace, blackout curtains, iron/ironing board

6. Holiday Inn Express Winchester South-Stephens City by IHG

Stephens City

Steven

S$120

includes taxes & fees

20 Sept - 21 Sept

Premium bedding, pillow-top beds, desk, iron/ironing board

7. Quality Inn Stephens City - Winchester South

Stephens City

Nancy

S$120

includes taxes & fees

27 Aug - 28 Aug

8. Hampton Inn Front Royal

Front Royal

Timothy

S$173

includes taxes & fees

27 Aug - 28 Aug

9. Country Inn & Suites by Radisson, Winchester, VA

Winchester

Phillip

S$134

includes taxes & fees

15 Sept - 16 Sept

10. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Adrian

S$181

includes taxes & fees

13 Sept - 14 Sept

11. TownePlace Suites by Marriott Front Royal

Front Royal

Justin

S$197

includes taxes & fees

17 Sept - 18 Sept

12. Spark by Hilton Winchester

Winchester

johnny

S$116

includes taxes & fees

17 Sept - 18 Sept

Desk, iron/ironing board (on request), free WiFi

13. Relax Inn Motel

Front Royal

Jamila

S$96

includes taxes & fees

26 Aug - 27 Aug

14. Motel 6 Front Royal, VA

Front Royal

Robert

S$99

includes taxes & fees

24 Aug - 25 Aug

In-room safe, desk, laptop workspace, blackout curtains

15. Baymont by Wyndham Front Royal Near Shenandoah National Park

Front Royal

Dave

S$85

includes taxes & fees

30 Aug - 31 Aug

16. Fairfield Inn & Suites by Marriott Winchester

Winchester

george

S$131

includes taxes & fees

27 Aug - 28 Aug

17. Super 8 by Wyndham Front Royal Near Shenandoah National Park

Front Royal

Snehil Meet

S$95

includes taxes & fees

2 Sept - 3 Sept

Desk, soundproofing, iron/ironing board (on request), cots/infant beds

18. Twi-Lite Inn

Front Royal

Jacob

S$116

includes taxes & fees

26 Aug - 27 Aug

19. La Quinta Inn & Suites by Wyndham Winchester

Winchester

chouaib

S$145

includes taxes & fees

23 Aug - 24 Aug

20. Home2 Suites By Hilton Winchester

Winchester

Jose

S$143

includes taxes & fees

31 Aug - 1 Sept

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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.

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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.

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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.

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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.

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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.

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Top Middletown Hotel Reviews

TRU By Hilton Winchester

10/10 Excellent

"We love Tru ! Everyone is very helpful . Rooms are clean . Easy check in and out . Breakfast is great ! We love stayingvthere !"

Quality Inn Winchester

8/10 Good

"Not bad for the price . Staff was very friendly and personable. Location was great . Overall a good place for a good night sleep while passing through area. Would use again while traveling"

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent

"Great location. Clean, comfortable, great breakfast options. Staff pleasant and helpful."

Hampton Inn Front Royal

10/10 Excellent

"Clean room, friendly staff, great included breakfast"

Spark by Hilton Winchester

10/10 Excellent

"Very clean and lovely. We enjoyed it"

Comfort Inn & Suites Winchester

10/10 Excellent

"Very well-maintained hotel. Friendly staff and great location."

Baymont by Wyndham Front Royal Near Shenandoah National Park

10/10 Excellent

"It was wonderful as always"

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent

"Stayed here as a halfway point between Charlotte, NC and NY. There's a Houlihan's attached to the hotel. It was nice to not have to leave the hotel for dinner after driving all day. We were traveling with 2 teenagers so booking a room with 2 queen beds and a sofabed was perfect. The 2 queen beds were in a separate room and had a nice large flatscreen TV. The living room with the sofabed also had a nice big flatscreen TV. There was a wetbar area above the refrigerator. Nice Crabtree & Evelyn bath products and I think this was the only place I've stayed recently that included a shower cap! Also, a sewing kit, which was a nice touch. Hilton Honors members get 2 free bottle of water and cookies on check in. Thrilled there was an allergy friendly cookie option since a few of us in the family are gluten & dairy free. The town itself also had lots of stores, restaurants and a starbucks. Also, if you're stil reading... the hotel is a mere 10 minutes from Dinosaurland which is a kitschy roadside attraction well worth the stop if you're into that sort of thing or have very young kids traveling with you :)"

Wayside Inn

8/10 Good

"Clean room at a reasonable price. Interesting old inn."

More cheap stays in Middletown

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

S$100

2 Sept - 3 Sept

includes taxes & fees