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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 61 Apartments in Middletown with updated reviews, rates, and availability.

The Queen of Winchester Three Bedroom with Upper Level Deck
Private kitchen

The Queen of Winchester Three Bedroom with Upper Level Deck

10.0 out of 10, Exceptional, (1)
"If you want to be in the town and have quick access to everything, this is the place for you."
The price is AED 246
AED 643 total
includes taxes & fees
9 Apr - 10 Apr
The Queen of Winchester Three Bedroom with Upper Level Deck
Front Royal Retreat on 3 Acres w/ Mtn Views!
Fridge, microwave, oven, dishwasher

Front Royal Retreat on 3 Acres w/ Mtn Views!

2.0 star property
10.0 out of 10, Exceptional, (2)
"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!
Nostalgia Lane in the heart of the city
Miscellaneous

Nostalgia Lane in the heart of the city

8.8 out of 10, Excellent, (5)
"We need overnight accommodations for our daughter’s surprise proposal. We checked into the VRBO and we were stunned! We walked around in silence taking in all of the charm, beauty and uniqueness of this home. This is a clean place with a very comfortable mattress! It is a fascinating place and we just loved it!! The host was very gracious and communicative - we wanted for nothing!! Five Starts "
The price is AED 731
AED 1,278 total
includes taxes & fees
6 Apr - 7 Apr
Nostalgia Lane in the heart of the city
Waterfront Virginia Retreat w/ Canoe, Pets Welcome
Property grounds

Waterfront Virginia Retreat w/ Canoe, Pets Welcome

10.0 out of 10, Exceptional, (45)
"This was a quiet, scenic and well appointed property. Our host was even kind enough to offer assistance when my car needed a jump. Something she found was happening from the neighbor. Great sense of community, great hospitality. The cows on the adjacent property behind the creek would walk down and graze and drink from the creek. It was magic. Thank you again. "
Waterfront Virginia Retreat w/ Canoe, Pets Welcome
Cozy English Basement Apt quiet but close to downtown
Miscellaneous

Cozy English Basement Apt quiet but close to downtown

9.4 out of 10, Exceptional, (6)
"Very cute place to stay at a perfect location to the little historic district of Winchester. Bed was comfortable but very small futon. We are tall people so it was not quite long enough for us. Bathroom was extremely small, doable for us but if we were bigger people it would be difficult to get into that space. Water pressure for sink was poor, shower was just okay. Quaint place with a friendly, engaged owner. We would go back just for the amazing location!"
The price is AED 331
AED 603 total
includes taxes & fees
4 Apr - 5 Apr
Cozy English Basement Apt quiet but close to downtown
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Exterior

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

9.0 out of 10, Wonderful, (4)
"We really like staying walking distance from the Historic District in Winchester and this was a great home base to do so. The whole process was seemless and easy. I will most likley try to come back for my conference next year. The place is clean and comfortable. Fun times "
The price is AED 753
AED 1,353 total
includes taxes & fees
6 Apr - 7 Apr
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Charming Front Royal Retreat ~ 1 Mi to River!
Microwave, stovetop, coffee/tea maker, toaster

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!
Morocco Loft 2BR overlooking city walking mall
Living area

Morocco Loft 2BR overlooking city walking mall

2.0 star property
10.0 out of 10, Exceptional, (2)
"Love the location, availability of parking, and the loft was very comfortable and had everything we needed."
Morocco Loft 2BR overlooking city walking mall
Apple Mountain Retreat
Property grounds

Apple Mountain Retreat

10.0 out of 10, Exceptional, (12)
"We enjoyed our stay! The amenities were better than advertised, and you can tell the owner put a lot of effort into making it an enjoyable experience."
The price is AED 551
AED 920 total
includes taxes & fees
4 Apr - 5 Apr
Apple Mountain Retreat
Modern Glass Retreat -All the modern amenities in a secluded forest setting
Exterior

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

9.0 out of 10, Wonderful, (12)
"It was the perfect house for a quick getaway for my husband and I. We loved the glass wall facing the woods and all the modern amenities. It’s close to many wineries and breweries and just a nice, quiet location if you’re looking for somewhere to go to unplug from daily life. We would definitely Italy come back."
The price is AED 900
AED 1,390 total
includes taxes & fees
7 Apr - 8 Apr
Modern Glass Retreat -All the modern amenities in a secluded forest setting
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Private kitchen

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

The price is AED 624
AED 785 total
includes taxes & fees
4 Apr - 5 Apr
Cozy studio close to Skyline Drive, Hiking, and Main Street.
The Blue Door steps from Handley Library
Miscellaneous

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 price is AED 422
AED 707 total
includes taxes & fees
13 Apr - 14 Apr
The Blue Door steps from Handley Library
Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly
Living area

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
Outdoor dining

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 731
AED 1,153 total
includes taxes & fees
7 Apr - 8 Apr
Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Terrace/patio

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

10.0 out of 10, Exceptional, (6)
"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 642
AED 1,035 total
includes taxes & fees
7 Apr - 8 Apr
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
The Stock Exchange downtown 3rd floor studio apt
Microwave, oven, stovetop

The Stock Exchange downtown 3rd floor studio apt

2.0 star property
6.0 out of 10, (1)
The price is AED 364
AED 682 total
includes taxes & fees
1 May - 2 May
The Stock Exchange downtown 3rd floor studio apt
The Outpost Suite 2- A Curated Farmhouse Suite
1 bedroom, WiFi

The Outpost Suite 2- A Curated Farmhouse Suite

6.6 out of 10, (7)
"The property is a bit off its prime... the deck in the back is not like it appears in the picture. Not a terrible property, but a bit run down. I did appreciate that we were the only ones there and quietness was good for a great nights sleep. Great areas to walk the dog. The property manager was very nice and helpful. Greeted us when we arrived and made sure we got in okay."
The Outpost Suite 2- A Curated Farmhouse Suite
Lofts for weekly rentals! 2 miles from historic downtown.
Fridge, microwave, stovetop, coffee/tea maker

Lofts for weekly rentals! 2 miles from historic downtown.

Lofts for weekly rentals! 2 miles from historic downtown.
Rosamond nice downtown studio apt
Miscellaneous

Rosamond nice downtown studio apt

8.0 out of 10, Very Good, (2)
"I made a quick last minute trip to Winchester to see family. I enjoyed my stay in the Studio and I would recommend it to anyone inquiring about the place. "
The price is AED 404
AED 707 total
includes taxes & fees
4 Apr - 5 Apr
Rosamond nice downtown studio apt
The Royal Loft, Modern 2 Bedroom, Front Royal, VA
Fridge, microwave, oven, stovetop

The Royal Loft, Modern 2 Bedroom, Front Royal, VA

9.6 out of 10, Exceptional, (5)
"Everything was excellent Great location. Enjoyed every thing about our visit to front royal"
The Royal Loft, Modern 2 Bedroom, Front Royal, VA
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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Other property types in Middletown

Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (308)
"We thoroughly enjoyed our stay here. From the moment you walk into the cabin, the views are spectacular and the surroundings are relaxing. We had a wonderful time and can’t wait to come back in the warmer weather to enjoy the outdoors more within a quick drive of lots of parks and scenic views Very clean and well appointed top-notch. "
Star view cabin-Riverfront
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (83)
"Loved it "
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Falling Leaf Cabin With Winter River And Mountain View!
Exterior

Falling Leaf Cabin With Winter River And Mountain View!

9.8 out of 10, Exceptional, (281)
"Fourth time here and it never gets old!!! absolutely gorgeous!"
Falling Leaf Cabin With Winter River And Mountain View!
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.

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: The Queen of Winchester Three Bedroom with Upper Level Deck: Situated in Winchester, 13.2 mi/21.2 km from the heart of Middletown. Includes private patios. Front Royal Retreat on 3 Acres w/ Mtn Views!: Located 10.7 mi/17.3 km away in Front Royal. Private patios, fireplaces, and sofa beds are included. WonderClock House downtown vintage duplex w/ porches, steps to Handley Library: It’s located in Winchester, 12.6 mi/20.2 km away. Nostalgia Lane in the heart of the city: 12.4 mi/20 km away in Winchester. Waterfront Virginia Retreat w/ Canoe, Pets Welcome: It’s located in Rileyville, 19.2 mi/30.9 km from Middletown. Includes private patios and fireplaces.
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. Shenandoah River and Cedar Creek and Belle Grove National Historical Park are a couple of scenic spots to enjoy the outdoors, whereas Wayside Theater is one of the cultural attractions. While here, Cedar Creek Battlefield Foundation and Belle Grove Plantation 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.