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Check prices for these dates

This weekend
26 Jun - 28 Jun
Next weekend
3 Jul - 5 Jul

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Our top choices for Middletown hotels

Breakfast area

1. Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (315 reviews)
"Clean and quiet"
United States
Cameron
The price is NZ$119
includes taxes & fees
29 June - 30 June
Econo Lodge Inn & Suites Middletown - Winchester South
Dining

2. Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (438 reviews)
"Nice historic place"
United States
Donna
The price is NZ$251
includes taxes & fees
23 June - 24 June
Wayside Inn
Exterior

3. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,120 reviews)
"Decent accommodations, friendly staff."
United States
Juliet
The price is NZ$196
includes taxes & fees
20 July - 21 July
Comfort Inn & Suites Winchester
Snack bar

4. TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (975 reviews)
"Great hotel good location"
United States
Federico
The price is NZ$149
includes taxes & fees
5 July - 6 July
TRU By Hilton Winchester
Restaurant

5. 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, (904 reviews)
"The room was very clean and the front desk staffs were very nice."
United States
Angelina
The price is NZ$225
includes taxes & fees
28 June - 29 June
Hampton Inn Winchester N/Conference Center, VA
Lobby

6. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,008 reviews)
"Excellent hotel, very clean, nice beds."
United States
Sarat
The price is NZ$173
includes taxes & fees
6 July - 7 July
Spark by Hilton Winchester
Exterior

7. 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, (1,006 reviews)
"Great hotel with helpful staff."
United States
Christy
The price is NZ$219
includes taxes & fees
2 July - 3 July
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
Free daily buffet breakfast

8. 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, (2,275 reviews)
"Breakfast was great and the staff were very nice!"
United States
Madeline
The price is NZ$220
includes taxes & fees
24 June - 25 June
La Quinta Inn & Suites by Wyndham Winchester
Exterior

9. Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,008 reviews)
"Breakfast was great and we love that they let us bring small dogs"
United States
Claire VanWinkle
The price is NZ$176
includes taxes & fees
28 June - 29 June
Quality Inn Winchester
Lobby

10. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (878 reviews)
"The room was clean and the breakfast was very good."
United States
Don
The price is NZ$176
includes taxes & fees
28 June - 29 June
Fairfield Inn & Suites by Marriott Winchester
Lobby

11. Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah
2.5 star property
Woodstock
8.8 out of 10, Excellent, (1,003 reviews)
"Always a great stay."
United States
Kenneth
The price is NZ$195
includes taxes & fees
28 June - 29 June
Comfort Inn Woodstock Shenandoah
Exterior

12. SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (862 reviews)
"Staff was very helpful, room was better than expected, pool was fantastic. Nice fitness center too."
United States
Chris
The price is NZ$215
includes taxes & fees
28 June - 29 June
SpringHill Suites by Marriott Winchester
Lobby

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

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
Front Royal
7.6 out of 10, Good, (1,002 reviews)
"room was clean and staff was friendly"
United States
Carol
The price is NZ$128
includes taxes & fees
7 July - 8 July
Super 8 by Wyndham Front Royal Near Shenandoah National Park
Lobby

14. Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.2 out of 10, Very good, (1,009 reviews)
"Everything thing was good and there is a Mexican bar and restaurant attached to hotel."
United States
Ronald
The price is NZ$163
includes taxes & fees
30 June - 1 July
Ramada by Wyndham Strasburg/Shenandoah Valley
Indoor pool, open 8 AM to 10 PM, pool loungers

15. Hampton Inn & Suites Woodstock, VA

Hampton Inn & Suites Woodstock, VA
2.5 star property
Woodstock
8.8 out of 10, Excellent, (1,004 reviews)
"Very nice and quiet stay"
United States
robert c
The price is NZ$214
includes taxes & fees
28 June - 29 June
Hampton Inn & Suites Woodstock, VA
Terrace/patio

16. Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
3.0 star property
Winchester
8.0 out of 10, Very good, (6 reviews)
"There was no shampoo nor shower gel and the shower was cool water. Takes 5 minutes to even get lukewarm water. No one at front desk to check out so ??? "
United States
Timothy
The price is NZ$204
includes taxes & fees
10 July - 11 July
Home2 Suites By Hilton Winchester
Exterior

17. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.2 out of 10, Wonderful, (1,001 reviews)
"Staff were polite and helpful, room was clean."
United States
Kimberly
The price is NZ$182
includes taxes & fees
5 July - 6 July
Holiday Inn Winchester Se-Historic Gateway by IHG
Lobby

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

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,004 reviews)
"Location is great, near popular restaurants. Bed was so comfortable! Staff was very friendly and helpful."
United States
Brenda
The price is NZ$183
includes taxes & fees
22 July - 23 July
Country Inn & Suites by Radisson, Winchester, VA
Lobby

19. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,456 reviews)
"Excellent stay"
United States
Michael
The price is NZ$177
includes taxes & fees
6 July - 7 July
Microtel Inn & Suites by Wyndham Winchester
Lobby

20. Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
Strasburg
9.0 out of 10, Wonderful, (1,001 reviews)
"It was a nice hotel for an over night stay. The room took a while to cool down but the overall stay was great."
United States
Joni
The price is NZ$229
includes taxes & fees
8 July - 9 July
Fairfield Inn & Suites Strasburg Shenandoah Valley
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

8.4/5 (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.
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
Photo by Stephanie Sutton
Open Photo by Stephanie Sutton

Top Middletown Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"We stayed there for 5 nights in a row and it was excellent. Huge/clean rooms. Perfect location for us. Friendly staff and they allowed us to park our bikes on the front porch."
Jordi 5-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Winchester

More cheap accommodation in Middletown

APM Inn & Suites

APM Inn & Suites

1347 Berryville Ave Winchester VA
The price is NZ$126 per night from 28 June to 29 June
NZ$126
28 June - 29 June
includes taxes & fees
7/10 Good! (460 reviews)

Frequently asked questions

Where is the best place for a stay in Middletown?
Based on our traveller data, Wayside Inn is one of the top choices for your stay. This hotel offers free parking and free WiFi. Econo Lodge Inn & Suites Middletown - Winchester South is another good choice for your stay. 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 3 hotels and other accommodation options to choose from. Find out more about Middletown.
What is there to see in Middletown?
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 Belle Grove Plantation 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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