Photo by Samantha Keyes

Middletown Hotels from S$77

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Middletown hotels

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
8.2 out of 10, Very good, (756)
"Always great!"
The price is S$111
includes taxes & fees
20 Jul - 21 Jul
Holiday Inn Express Winchester South-Stephens City by IHG

Fairfield Inn & Suites by Marriott Winchester

2.5 star property
9.0 out of 10, Wonderful, (735)
"Clean and comfortable room, wonderful breakfast, pleasant personnel"
The price is S$135
includes taxes & fees
31 Jul - 1 Aug
Fairfield Inn & Suites by Marriott Winchester

Relax Inn Motel

2.0 star property
8.2 out of 10, Very good, (235)
"Clean, quiet and convenient. Check in process was quick and easy, with the very friendly and helpful staff. I would absolutely stay here again."
The price is S$99
includes taxes & fees
18 Jul - 19 Jul
Relax Inn Motel

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (401)
"We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere. "
The price is S$161
includes taxes & fees
20 Jul - 21 Jul
Wayside Inn

Econo Lodge Inn & Suites

2.0 star property
5.6 out of 10, (283)
"Great place to sleep and its was very quiet. "
The price is S$96
includes taxes & fees
23 Jul - 24 Jul
Econo Lodge Inn & Suites

Quality Inn

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Great place , great front desk staff, super clean & very quiet"
The price is S$129
includes taxes & fees
23 Jul - 24 Jul
Quality Inn

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
8.8 out of 10, Excellent, (1001)
"Great stay for a great price!"
The price is S$136
includes taxes & fees
20 Jul - 21 Jul
Country Inn & Suites by Radisson, Winchester, VA

Super 8 by Wyndham Front Royal

2.0 star property
7.4 out of 10, Good, (1007)
"Great place"
The price is S$106
includes taxes & fees
23 Jul - 24 Jul
Super 8 by Wyndham Front Royal

Comfort Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (1008)
"Would stay again. "
The price is S$135
includes taxes & fees
27 Jul - 28 Jul
Comfort Inn & Suites

Motel 6 Winchester, VA

2.0 star property
8.2 out of 10, Very good, (1000)
"Great for an overnight stay. Clean room. Needs comfortable chairs."
The price is S$93
includes taxes & fees
22 Jul - 23 Jul
Motel 6 Winchester, VA

Travelodge by Wyndham Winchester

2.5 star property
8.4 out of 10, Very good, (1106)
"The stay was great for the price."
The price is S$96
includes taxes & fees
21 Jul - 22 Jul
Travelodge by Wyndham Winchester

TownePlace Suites by Marriott Winchester

3.0 star property
8.8 out of 10, Excellent, (444)
"Staff was amazing! "
The price is S$149
includes taxes & fees
21 Jul - 22 Jul
TownePlace Suites by Marriott Winchester

Hampton Inn Winchester N/Conference Center, VA

2.5 star property
9.2 out of 10, Wonderful, (782)
"Well kept, clean, good breakfast."
The price is S$172
includes taxes & fees
25 Jul - 26 Jul
Hampton Inn Winchester N/Conference Center, VA

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
9.2 out of 10, Wonderful, (1303)
"Clean comfortable room, friendly staff. "
The price is S$122
includes taxes & fees
17 Aug - 18 Aug
Microtel Inn & Suites by Wyndham Winchester

Holiday Inn Express Hotel & Suites Winchester by IHG

2.5 star property
8.8 out of 10, Excellent, (763)
"Very friendly staff and clean property"
The price is S$155
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn Express Hotel & Suites Winchester by IHG

Candlewood Suites Winchester by IHG

2.5 star property
8.8 out of 10, Excellent, (478)
"great for overnight stay "
The price is S$127
includes taxes & fees
19 Jul - 20 Jul
Candlewood Suites Winchester by IHG

Quality Inn Stephens City - Winchester South

2.5 star property
8.0 out of 10, Very good, (589)
"Really close to highway, with few good dining options near by, room was clean however it was sligltly outdated, breakfast was decent, eggs were good. "
The price is S$113
includes taxes & fees
31 Jul - 1 Aug
Quality Inn Stephens City - Winchester South

Sleep Inn & Suites

2.5 star property
8.0 out of 10, Very good, (1014)
"Comfortable, well priced, good breakfast "
The price is S$100
includes taxes & fees
17 Aug - 18 Aug
Sleep Inn & Suites

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
8.2 out of 10, Very good, (1004)
"Great location off the highway, restaurant on site was very good, staff was friendly and quick check in"
The price is S$102
includes taxes & fees
17 Aug - 18 Aug
Ramada by Wyndham Strasburg/Shenandoah Valley

SpringHill Suites by Marriott Winchester

2.5 star property
9.4 out of 10, Exceptional, (655)
"Great Location. Great stay "
The price is S$162
includes taxes & fees
3 Aug - 4 Aug
SpringHill Suites by Marriott 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.
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Middletown

Middletown awaits: its entertainment, churches, bars and more!

Photo by Stephanie Sutton
Open Photo by Stephanie Sutton

Top Middletown Hotel Reviews

Frequently asked questions

Where is the best place for a stay in Middletown?

Wayside Inn is a favourite with Expedia customers. This hotel offers a restaurant and free parking. Another top choice for your trip based on traveller reviews is Econo Lodge Inn & Suites. See all available top hotels, or 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 the best family accommodation in Middletown?

Wayside Inn is a hotel with a restaurant and free parking, and it's a top choice on Expedia for families. Econo Lodge Inn & Suites is another good choice for your family trip. Also, attractions in the area such as Dinosaur Land and Secret Passage Ranch are fun for children of all ages. Find more child-friendly accommodations in Middletown.

What's the best hotel for a couple visiting Middletown?

Wayside Inn is a favourite hotel for couples, and features cable TV and wedding services. See all romantic hotels in Middletown.

What's the best dog-friendly place to stay in Middletown?

Econo Lodge Inn & Suites is a top hotel for people travelling with their pets, and offers a bar/lounge and free WiFi for its human guests. See more pet-friendly hotel accommodations in Middletown.

What are some hotels with pools in Middletown?

La Quinta Inn & Suites by Wyndham Winchester: Provides buffet, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn Winchester Se-Historic Gateway by IHG and Microtel Inn & Suites by Wyndham Winchester are a couple of other choices that offer an on-site pool. View all hotels with pools 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 4 hotels and other accommodation options to choose from. Find out more about Middletown.

What is there to see in Middletown?

Landmarks like Cedar Creek Battlefield Foundation and Belle Grove Plantation might be worth a visit. The picturesque setting of Cedar Creek and Belle Grove National Historical Park and Shenandoah River exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Jackson's Chase Golf Course and Wayside Theater. 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.