Middletown Holiday Rentals, Virginia: Private House Rentals

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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

Reserve now, pay later

Hotel

Spa

Breakfast, lunch, dinner and brunch served

1. Wayside Inn

Middletown

Christine

3.176.496 ₫

3.764.853 ₫ total

includes taxes & fees

18 Aug - 19 Aug

Standard Room, 1 King Bed with Sofa bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

2. Econo Lodge Inn & Suites Middletown - Winchester South

Middletown

Nathan

1.688.902 ₫

1.862.859 ₫ total

includes taxes & fees

6 Sept - 7 Sept

3. La Quinta Inn & Suites by Wyndham Winchester

Winchester

chouaib

2.800.022 ₫

3.116.424 ₫ total

includes taxes & fees

18 Aug - 19 Aug

4. Fairfield Inn & Suites by Marriott Winchester

Winchester

george

2.422.242 ₫

2.695.954 ₫ total

includes taxes & fees

20 Aug - 21 Aug

Room, 2 Queen Beds, Non Smoking | Desk, blackout curtains, iron/ironing board, free WiFi

5. Comfort Inn & Suites Winchester

Winchester

Richard

2.528.648 ₫

2.814.385 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Hypo-allergenic bedding, desk, blackout curtains, iron/ironing board

6. Hampton Inn Front Royal

Front Royal

Timothy

3.194.274 ₫

3.555.227 ₫ total

includes taxes & fees

23 Aug - 24 Aug

Room, 2 Queen Beds, Non Smoking | Desk, laptop workspace, iron/ironing board, free cots/infant beds

7. Microtel Inn & Suites by Wyndham Winchester

Winchester

Cheryl

2.300.672 ₫

2.560.648 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Suite, 1 King Bed (Additional Living Area) | In-room safe, desk, laptop workspace, blackout curtains

8. Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

Jennifer

2.431.392 ₫

2.784.571 ₫ total

includes taxes & fees

23 Aug - 24 Aug

9. TRU By Hilton Winchester

Winchester

Kelly

2.551.132 ₫

2.839.409 ₫ total

includes taxes & fees

27 Aug - 28 Aug

10. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Adrian

3.194.274 ₫

3.523.284 ₫ total

includes taxes & fees

24 Aug - 25 Aug

Suite, 1 King Bed, Smoking | In-room safe, desk, iron/ironing board, free cots/infant beds

Suite, 1 King Bed, Smoking | Living area | LED TV

11. Travelodge by Wyndham Winchester

Winchester

Jeffrey

1.803.936 ₫

1.989.820 ₫ total

includes taxes & fees

18 Aug - 19 Aug

Suite, 1 Bedroom | Living area | 48-inch flat-screen TV with cable channels, TV

12. Spark by Hilton Winchester

Winchester

Joscelyn

2.018.578 ₫

2.287.050 ₫ total

includes taxes & fees

2 Sept - 3 Sept

13. Quality Inn Winchester

Winchester

Scott

2.200.018 ₫

2.448.620 ₫ total

includes taxes & fees

23 Aug - 24 Aug

14. Fairfield Inn & Suites Strasburg Shenandoah Valley

Strasburg

Glenn

2.644.466 ₫

2.943.290 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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

15. Twi-Lite Inn

Front Royal

Jacob

2.143.808 ₫

2.386.163 ₫ total

includes taxes & fees

18 Aug - 19 Aug

Studio, 1 King Bed, Non Smoking, Refrigerator & Microwave (Wet bar) | Premium bedding, pillow-top beds, in-room safe, desk

16. Hampton Inn Winchester N/Conference Center, VA

Winchester

Brian

2.765.512 ₫

3.133.325 ₫ total

includes taxes & fees

30 Aug - 31 Aug

17. SpringHill Suites by Marriott Winchester

Winchester

Michael

2.967.867 ₫

3.303.236 ₫ total

includes taxes & fees

8 Sept - 9 Sept

Room, 2 Queen Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board

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

Winchester

Roger

2.471.131 ₫

2.750.368 ₫ total

includes taxes & fees

8 Sept - 9 Sept

19. Motel 6 Front Royal, VA

Front Royal

Robert

1.699.099 ₫

1.891.097 ₫ total

includes taxes & fees

1 Sept - 2 Sept

Studio Suite, 1 Bedroom | In-room safe, desk, laptop workspace, blackout curtains

Studio Suite, 1 Bedroom | Private kitchen | Coffee/tea maker, fridge, microwave, stovetop

20. Candlewood Suites Winchester by IHG

Winchester

Bridget

2.196.096 ₫

2.444.203 ₫ total

includes taxes & fees

23 Aug - 24 Aug

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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

Spark by Hilton Winchester

10/10 Excellent

"The person working at reception on Saturday, August 15 (from midday through evening) was so helpful and nice. She deserves a raise or promotion if she wants it!"

Quality Inn Winchester

10/10 Excellent

"The hotel is in a centric location. Denny's rest just next door."

Comfort Inn & Suites Winchester

10/10 Excellent

"What a great shower...glass doors, excellent water pressure, great shower head and so clean!"

Hampton Inn & Suites Woodstock, VA

10/10 Excellent

"The reception people was helpful .every thing was perfect"

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent

"All good!"

Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent

"Overall very well, room was old but clean, i like free parking Breakfast was Small but ok Cofee not strong enough for me"

Courtyard by Marriott Winchester

10/10 Excellent

"Easy check in, nice staff, clean room, comfortable bed. I would prefer a walk in shower as I’m sure a lot of customers would"

Hampton Inn Front Royal

10/10 Excellent

"This is the 2nd year we have stayed at your hotel. Your location, cleanliness, & service is great for our needs."

More cheap stays in Middletown

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

1.803.936 ₫

1.989.820 ₫ total

18 Aug - 19 Aug

includes taxes & fees