A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

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Our top choices for Middletown hotels

1. Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (465 reviews)
"We enjoyed our short stay at Wayside. We were greeted by Amanda with a very warm and friendly welcome. She kindly let us check in early and gave us a few ideas to explore."
United States
Gerry
The price is NZ$148
includes taxes & fees
14 Dec - 15 Dec
Wayside Inn

2. Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (334 reviews)
"Place is in poor repair."
United States
Craig
The price is NZ$129
includes taxes & fees
14 Dec - 15 Dec
Econo Lodge Inn & Suites Middletown - Winchester South

3. Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.2 out of 10, Very good, (1,030 reviews)
"Good breakfast and we can bring the dog."
United States
Angela
The price is NZ$152
includes taxes & fees
22 Nov - 23 Nov
Ramada by Wyndham Strasburg/Shenandoah Valley

4. 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, (926 reviews)
"Great hotel"
United States
Michael
The price is NZ$145
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn Express Winchester South-Stephens City by IHG

5. Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
Strasburg
9.0 out of 10, Wonderful, (1,000 reviews)
"Very clean room and property. Staff was great. Breakfast was good."
United States
Kayla
The price is NZ$242
includes taxes & fees
22 Nov - 23 Nov
Fairfield Inn & Suites Strasburg Shenandoah Valley

6. Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South
2.5 star property
Stephens City
8.0 out of 10, Very good, (726 reviews)
"Rooms were clean and comfortable"
United States
Jeanne
The price is NZ$152
includes taxes & fees
5 Dec - 6 Dec
Quality Inn Stephens City - Winchester South

7. Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.2 out of 10, Wonderful, (1,001 reviews)
"Perfect spot for a trip to Front Royal. Staff were great - especially Ryan at the front desk who checked us in. Room was extremely comfortable and breakfast was good."
United States
Charlotte
The price is NZ$237
includes taxes & fees
3 Dec - 4 Dec
Hampton Inn Front Royal

8. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,155 reviews)
"Convenient to the highway and reasonably priced."
United States
Donna S.
The price is NZ$186
includes taxes & fees
23 Nov - 24 Nov
Comfort Inn & Suites Winchester

9. 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, (1,003 reviews)
"It was a nice stay.. third time staying… relaxing and peaceful"
United States
Adrian
The price is NZ$227
includes taxes & fees
22 Nov - 23 Nov
DoubleTree by Hilton Front Royal Blue Ridge Shadows

10. 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, (1,001 reviews)
"Comfortable bed, friendly staff, and convenient location"
United States
Zohair
The price is NZ$173
includes taxes & fees
6 Dec - 7 Dec
Country Inn & Suites by Radisson, Winchester, VA

11. TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
Front Royal
9.6 out of 10, Exceptional, (620 reviews)
"Cleaned, maintained hotel near many conveniences."
United States
JoEllen
The price is NZ$256
includes taxes & fees
12 Dec - 13 Dec
TownePlace Suites by Marriott Front Royal

12. 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, (2,271 reviews)
"Great place to stay the night after a long drive"
United States
lucy
The price is NZ$186
includes taxes & fees
6 Dec - 7 Dec
La Quinta Inn & Suites by Wyndham Winchester

13. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (1,002 reviews)
"Clean room, great staff, good parking and free breakfast"
United States
Albert
The price is NZ$133
includes taxes & fees
29 Nov - 30 Nov
Spark by Hilton Winchester

14. Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (52 reviews)
"Clean rooms , friendly staff."
United States
Jean
The price is NZ$181
includes taxes & fees
22 Nov - 23 Nov
Home2 Suites By Hilton Winchester

15. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (977 reviews)
"Great place to stay in Winchester."
United States
Thomas
The price is NZ$186
includes taxes & fees
29 Nov - 30 Nov
Fairfield Inn & Suites by Marriott Winchester

16. TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,000 reviews)
"Rooms good sized, beds comfortable, quiet ( slept great), great breakfast. Highly recommend!!"
United States
Jesse
The price is NZ$163
includes taxes & fees
29 Nov - 30 Nov
TRU By Hilton Winchester

17. 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, (966 reviews)
"The breakfast was delicious, it was very welcoming very clean best ever had at motel"
United States
Elizabeth
The price is NZ$217
includes taxes & fees
21 Nov - 22 Nov
Hampton Inn Winchester N/Conference Center, VA

18. 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
7.8 out of 10, Good, (1,001 reviews)
"Great location and comfortable room."
United States
Amelia
The price is NZ$137
includes taxes & fees
3 Dec - 4 Dec
Super 8 by Wyndham Front Royal Near Shenandoah National Park

19. 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, (1,006 reviews)
"Great hotel."
United States
Nicholas
The price is NZ$205
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG

20. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,442 reviews)
"Perfect accommodation- great breakfast and attentive gracious staff"
United States
Kathleen
The price is NZ$160
includes taxes & fees
22 Nov - 23 Nov
Microtel Inn & Suites by Wyndham Winchester
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.

Hotels recommended for families in Middletown

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Stay near popular Middletown attractions

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.

A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

Top Middletown Hotel Reviews

Recent Reviews in Middletown

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Frequently asked questions

What is the best area to stay in Middletown?
The best area to stay in Middletown is the historic downtown area, particularly around Main Street.

This quaint area is the heart of Middletown, offering a relaxed pace with its collection of historic buildings and local businesses. You'll find a few independent shops and eateries dotted along Main Street, providing a pleasant environment for a stroll. The main crossroads of Main Street and Fairfax Street marks the centre of this small but welcoming community.

Couples looking for a peaceful getaway will find downtown Middletown perfect. It offers a quiet setting for a romantic break, with the convenience of local dining options within walking distance.
What are the best hotels in Middletown that travellers recommend?
Two of the best hotels in Middletown that receive consistently high recommendations from travellers are the Wayside Inn and the Econo Lodge Inn & Suites.

The Wayside Inn, a hotel, has an excellent 9.2 rating. Guests frequently mention the comfortable and clean rooms, the incredible food, and the helpful staff. It also offers evening entertainment and is located just 2.0 km from Cedar Creek and Belle Grove National Historical Park.

Another highly recommended option is the Econo Lodge Inn & Suites. This hotel is praised for its clean and spotless rooms and offers convenient amenities such as free accessible parking and RV, bus, and truck parking.
What are the best family hotels in Middletown?
For family-friendly accommodation in Middletown, consider the Wayside Inn or the Econo Lodge Inn & Suites.

The Wayside Inn, with an excellent 9.2 rating, is a great choice for families. It offers highchairs for children and free rollaway extra beds, along with early check-in options. Guests frequently mention the comfortable and clean rooms, the incredible food, and the friendly, helpful staff. The hotel is also conveniently located just 2.0 km from Cedar Creek and Belle Grove National Historical Park.

Another option is the Econo Lodge Inn & Suites, which provides free cribs and sofa beds, making it suitable for families. Guests appreciate the clean and spotless rooms, and free self-parking and free WiFi are also available.
What are the top pet-friendly hotels in Middletown?
For top pet-friendly accommodation in Middletown, the Econo Lodge Inn & Suites is a great choice.

The Econo Lodge Inn & Suites is a practical option for travellers with pets, as pets are permitted at this establishment. Guests have frequently commented on the clean and spotless rooms. The hotel also offers free WiFi and complimentary self-parking, along with free cribs for those travelling with infants.
What are the best budget hotels in Middletown?
For a highly-rated budget option in Middletown, the Econo Lodge Inn & Suites is a good choice.

This hotel offers complimentary self-parking and free WiFi. Guests appreciate the clean and spotless rooms, and for those travelling with infants, free cribs are available. Early check-in can also be arranged.
What are the most romantic hotels in Middletown for couples?
For a romantic stay in Middletown, the Wayside Inn is an excellent choice for couples.

The Wayside Inn, a hotel with an impressive 9.2 rating, is particularly well-suited for couples, offering a dedicated couples dining experience. Guests frequently highlight the comfortable and clean rooms, incredible food, and the very helpful staff. The hotel also provides free WiFi and free self-parking, and is conveniently located just 2.0 km from Cedar Creek and Belle Grove National Historical Park, making it ideal for exploring local attractions together.
What are the best hotels in Middletown near Cedar Creek and Belle Grove National Historical Park?
For a hotel in Middletown conveniently located near Cedar Creek and Belle Grove National Historical Park, the Wayside Inn is an excellent choice.

This hotel, with an impressive 9.2 rating, is situated just 2.0 km from the historical park, making it very accessible for visits. Guests frequently praise the comfortable and clean rooms, as well as the incredible and amazing food. The staff are consistently described as very friendly and helpful. Families will appreciate the availability of highchairs for children and free rollaway extra beds. The hotel also offers early check-in options, which can be convenient for travellers. Its beautiful decor and a great bar further enhance the guest experience.
When is the best time to go to Middletown?
The best time to visit Middletown, Virginia, is during the spring (April to May) and autumn (September to October) months.

These seasons offer pleasant weather, with mild temperatures and lower humidity, making it ideal for exploring the area's natural beauty and historical sites. Spring brings blooming flowers and lush greenery, while autumn showcases stunning fall foliage.

Couples looking for a romantic getaway will appreciate the comfortable climate for leisurely walks through historic downtown or visits to local vineyards. The picturesque scenery during these months also provides a lovely backdrop for outdoor activities.

Families travelling with children will find these seasons superb for enjoying outdoor attractions without the discomfort of extreme heat or cold.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to 'My Trips' and selecting your reservation. To find flexible deals, filter your search by 'Fully refundable property' for hotels in Middletown.
How can I save on a hotel booking in Middletown with Expedia?
One Key™—Expedia's free travel rewards programme—gives you instant access to discounts with Member Prices on Middletown hotels. Plus, you'll earn OneKeyCashā„¢* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Middletown?
Prices for hotels in Middletown often vary, but you can find a great deal from NZ$121 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by 'Price: low to high' for our cheapest rates.

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