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Compare 57 Apartments in Middletown with updated reviews, rates, and availability.

Cozy studio close to Skyline Drive, Hiking, and Main Street.

9.0 out of 10, Wonderful, (2)
"Spent the day in the park , very convenient "
The price is AED 624
AED 777 total
includes taxes & fees
19 Jun - 20 Jun
Cozy studio close to Skyline Drive, Hiking, and Main Street.

Charming Loft In Winchester Va, Furnished and all Inclusive

Charming Loft In Winchester Va, Furnished and all Inclusive

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

10.0 out of 10, Exceptional, (7)
"2 night stay celebrating our 21 year anniversary! Host was attentive & communicated through text daily to check how our stay was going! Unique property grounds & highly enjoyable!"
The price is AED 565
AED 930 total
includes taxes & fees
11 Jun - 12 Jun
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

The Queen of Winchester Three Bedroom with Upper Level Deck

8.4 out of 10, Very Good, (5)
"If you want to be in the town and have quick access to everything, this is the place for you."
The Queen of Winchester Three Bedroom with Upper Level Deck

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

8.8 out of 10, Excellent, (5)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
The price is AED 753
AED 1,332 total
includes taxes & fees
15 Jun - 16 Jun
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

Front Royal Retreat on 3 Acres w/ Mtn Views!

2.0 star property
8.4 out of 10, Very Good, (6)
"House and overall property was very clean and we really enjoyed it and the spring water was amazing"
Front Royal Retreat on 3 Acres w/ Mtn Views!

Apple Mountain Retreat

10.0 out of 10, Exceptional, (13)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is AED 529
AED 895 total
includes taxes & fees
9 Jun - 10 Jun
Apple Mountain Retreat

Waterfront Virginia Retreat w/ Canoe, Pets Welcome

10.0 out of 10, Exceptional, (47)
"Awesome place if you enjoy the outdoors or just beautiful scenery"
Waterfront Virginia Retreat w/ Canoe, Pets Welcome

Berryville Bliss: Basement Apartment in welcoming Berryville

10.0 out of 10, Exceptional, (1)
"Very comfortable, clean, and spacious. Safe, easy to navigate neighborhood. I was there for two nights for a Trackdaze event at Summit Point. It’s a great place to stay."
Berryville Bliss: Basement Apartment in welcoming Berryville

Morocco Loft 2BR overlooking city walking mall

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great property with all the comforts of home"
Morocco Loft 2BR overlooking city walking mall

New - The Skyline Flat

10.0 out of 10, Exceptional, (1)
"We had an absolutely wonderful stay! The location was perfect as it was just minutes from the Appalachian Trail and close to downtown, which made exploring and dining out super convenient. The home itself was beautifully furnished, spotless, and incredibly comfortable. We slept so well and didn’t have any significant street noise. A special shoutout to our host, who went above and beyond to make sure we were well situated. They were incredibly responsive, kind, and even gave us an excellent...
New - The Skyline Flat

Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly

2.0 out of 10, (1)
"For a new listing to VRBO, the property did not meet our expectations. Check in time on app was incorrect delaying our activities. Communication with owner was delay and resulted in conversation with VRBO. Pictures of apartment were not accurate to the unit. The property is in a "Corporate Apartment" complex but apartment is nowhere near the standards of a corporate apartment. The cable remote didn't work. TV in bedroom was plugged in but no cable hook up. Windowsill and door frame damaged by...
Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly

Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks

10.0 out of 10, Exceptional, (4)
"Amazing little place on the Shenandoah. Fire pit and hot tub are amazing touches. Will stay here again. "
The price is AED 767
AED 1,194 total
includes taxes & fees
24 Jun - 25 Jun
Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks

Modern Glass Retreat -All the modern amenities in a secluded forest setting

9.0 out of 10, Wonderful, (14)
"Had an amazing stay! Beautiful unit in pristine location. Hope we can go back. Host very accommodating. Memorable stay. "
The price is AED 975
AED 1,448 total
includes taxes & fees
20 Jun - 21 Jun
Modern Glass Retreat -All the modern amenities in a secluded forest setting

Cozy English Basement Apt quiet but close to downtown

9.6 out of 10, Exceptional, (7)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
Cozy English Basement Apt quiet but close to downtown

Nostalgia Lane in the heart of the city

9.0 out of 10, Wonderful, (9)
"We enjoyed the small town feel of Winchester. Our stay here was the cherry on top. Such a beautiful place with so much personality, we will definitely be back!!!!"
Nostalgia Lane in the heart of the city

Charming Front Royal Retreat ~ 1 Mi to River!

10.0 out of 10, Exceptional, (1)
"We arrived in the afternoon before a festival. Main street was closed, but we were still able to access the parking. Everything was clean, and we had a comfortable stay. There were restaurants and entertainment right outside. The only thing not in easy walking distance was a drugstore/CVS. I highly recommend staying at this location."
Charming Front Royal Retreat ~ 1 Mi to River!

The Blue Door steps from Handley Library

2.0 star property
6.0 out of 10, (1)
"While the owner could not have been nicer, VRBO dropped the ball. We did not get check in information, though the host provided it directly on hour after check-in time.The host needs to check in with the cleaners and visit the property. I say this as a landlord. We had one washcloth for two guests, no coffee or tea service, no tissues, no dish rag. The place looks a little run down and needs a refresh. Doors were broken, bathroom racks about to fall off the wall, and one soap dispenser was...
The Blue Door steps from Handley Library

Cameron Grace Brand New 1BR 1BA apt downtown Winchester

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great location, easy to find, easy to get in and out of, close to everything we wanted to do."
The price is AED 569
AED 920 total
includes taxes & fees
15 Jun - 16 Jun
Cameron Grace Brand New 1BR 1BA apt downtown Winchester

Waterfront Virginia Retreat w/ Canoe, Pets Welcome

3.0 star property
10.0 out of 10, Exceptional, (1)
Waterfront Virginia Retreat w/ Canoe, Pets Welcome
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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Frequently asked questions

What's it like to stay at an apartment in Middletown?
You’ll find 5 hotels and other accommodations in Middletown. Though there aren’t many apartments, we can help you locate accommodations with similar amenities. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. You can even filter by similar properties such as condos, vacation homes, or cottages. While exploring the local area, you might want to visit the bars and restaurants.
Are you thinking about apartments over traditional hotel rooms?
Often offering more space than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for couples looking for something with a more local feel.
What's a favorite apartment I should consider for a stay in Middletown?
Listed below are some of the more popular apartments in the area: Cozy studio close to Skyline Drive, Hiking, and Main Street.: Situated in Front Royal, 9.2 mi/14.8 km from the heart of Middletown. Apple Mountain Retreat: Located 11.6 mi/18.7 km away in Linden. Free WiFi, private patios, and Smart TVs are included. Access to onsite laundry facilities is available on site. Charming Loft In Winchester Va, Furnished and all Inclusive: It’s located in Winchester, 9.5 mi/15.3 km away. Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks: Located 16.4 mi/26.4 km away in Rileyville. Private balconies and sofa beds are included. Access to a hot tub is available on site. The Queen of Winchester Three Bedroom with Upper Level Deck: Located in Winchester, 13.2 mi/21.2 km from Middletown. Includes private patios. Access to onsite laundry facilities is available on site.
What can I expect from the weather when I travel to Middletown?
Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Middletown. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Middletown is 43 inches.
What are the must-see places to visit in Middletown?
Middletown is known for its bars and restaurants. Cedar Creek and Belle Grove National Historical Park and Shenandoah River are a couple of scenic spots to enjoy the outdoors, whereas Wayside Theater is one of the cultural attractions. While here, Belle Grove Plantation and Cedar Creek Battlefield Foundation are other places worth a visit.
What's the best way to get to and around Middletown?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 30.4 mi (48.9 km) from the heart of the city. If you’d like to venture out around the area, you may want to rent a car for your trip.