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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 49 Apartments in Middletown with updated reviews, rates, and availability.

Nostalgia Lane in the heart of the city
Private kitchen

Nostalgia Lane in the heart of the city

9.6 out of 10, Exceptional, (4)
"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 1,273 total
includes taxes & fees
2 Feb - 3 Feb
Nostalgia Lane in the heart of the city
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Room

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

The price is AED 624
AED 793 total
includes taxes & fees
1 Feb - 2 Feb
Cozy studio close to Skyline Drive, Hiking, and Main Street.
The Queen of Winchester Three Bedroom with Upper Level Deck
Queen living room main (1)

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 253
AED 628 total
includes taxes & fees
1 Feb - 2 Feb
The Queen of Winchester Three Bedroom with Upper Level Deck
Cozy English Basement Apt quiet but close to downtown
Room

Cozy English Basement Apt quiet but close to downtown

10.0 out of 10, Exceptional, (2)
"Downtown Winchester is charming, and the property was an easy walk from downtown (though in a safe suburban neighborhood). The property itself was just as advertised. I was able to cook meals there; the bed was comfortable; it was much nicer and more varied than a hotel room."
The price is AED 331
AED 603 total
includes taxes & fees
1 Feb - 2 Feb
Cozy English Basement Apt quiet but close to downtown
Morocco Loft 2BR overlooking city walking mall
Room

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
Exterior

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 588
AED 960 total
includes taxes & fees
2 Feb - 3 Feb
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

8.8 out of 10, Excellent, (11)
"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 1,381 total
includes taxes & fees
3 Mar - 4 Mar
Modern Glass Retreat -All the modern amenities in a secluded forest setting
Front Royal Retreat on 3 Acres w/ Mtn Views!
Front Royal Vacation Rental | 2BR | 2BA | 1,100 Sq Ft | Stairs Required

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!
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Comfy sleeper sofa surrounded by stunning views!

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 541
AED 887 total
includes taxes & fees
2 Feb - 3 Feb
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks
High-quality pullout queen sofa bed (it’s very comfortable and large)

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 553
AED 904 total
includes taxes & fees
2 Feb - 3 Feb
Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks
The Blue Door steps from Handley Library
Living area

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
7 Feb - 8 Feb
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
Yellow Submarine trendy basement apt and courtyard
Room

Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
The Outpost Suite 2- A Curated Farmhouse Suite
Outdoor dining

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

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

8.0 out of 10, Very Good, (2)
"This is a wonderful historic house in Old Town Winchester. The house is a duplex and is very room. It has the charm of a historic house, but modern amenities. It is very comfortable and check-in was extremely easy (we ended up arriving much later than we had planned, but had no problems accessing the house). The location is absolutely perfect, especially if you want to be in walking distance to all of the cute shops, cafes, and restaurants in the area. Our trip was very fast. We were in town...
The price is AED 753
AED 1,344 total
includes taxes & fees
2 Mar - 3 Mar
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Rosamond nice downtown studio apt
Living area

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
7 Feb - 8 Feb
Rosamond nice downtown studio apt
Waterfront Virginia Retreat w/ Canoe, Pets Welcome
Rileyville Vacation Rental | Studio | 1BA | 650 Sq Ft | 1 Step to Access

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
The Royal Loft, Modern 1 Bedroom, Front Royal, VA
Kitchen and Dining Area (1)

The Royal Loft, Modern 1 Bedroom, Front Royal, VA

The price is AED 459
AED 1,088 total
includes taxes & fees
24 Feb - 25 Feb
The Royal Loft, Modern 1 Bedroom, Front Royal, VA
The Outpost Suite 3 - Whimsical Farmhouse Retreat
Room

The Outpost Suite 3 - Whimsical Farmhouse Retreat

7.8 out of 10, Good, (9)
"The property includes three separate units within one house, and we experienced several issues during our stay. We arrived at night and found no lights to guide us, making it difficult to locate where we were staying. The main house door was unlocked, and the back door was wide open, which raised concerns about security. Assuming the main house was our accommodation, we entered and walked through it. However, with the back door open, we were worried someone might be inside who shouldn’t...
The Outpost Suite 3 - Whimsical Farmhouse Retreat
Cameron Grace Brand New 1BR 1BA apt downtown Winchester
Room

Cameron Grace Brand New 1BR 1BA apt downtown Winchester

2.0 star property
10.0 out of 10, Exceptional, (2)
"I stayed local over night for NYE. My first Vrbo ever. I hate technology so using the app for everything is not my favorite; but this was easy and fast. The apartment was super clean and adorable. Instructions were clear and it was easy check in. The apt had everything we needed, even a blow dryer. It poured that night, so i was grateful for that. Thanks! "
The price is AED 569
AED 932 total
includes taxes & fees
7 Feb - 8 Feb
Cameron Grace Brand New 1BR 1BA apt downtown 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.
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Other property types in Middletown

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Exterior

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (175)
"The location was exactly what we needed and wanted. If you want to totally relax, get semi off the grid, this is your place. Take a hike and take it all in. Thank you to our hosts for making such a great property available."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Mountain Views, River Frontage & HotTub + Country!
Angler hot tub in private pavilion

Mountain Views, River Frontage & HotTub + Country!

10.0 out of 10, Exceptional, (25)
"My wife, son (3yrs), and I stayed at the Angler Cabin for 3days/ 2nights. The description was accurate and cabin was well looked after/ clean. Directions were accurate (Google Maps was able to locate property no problem) and we were well prepared with some food/ drink supplies so we could make sure of the small kitchen. The road leading to the cabin is truly 10-15min of near off-road driving so winter condition could play a huge role in someone's stay by my 4WD truck had no issue.We spend a full...
Mountain Views, River Frontage & HotTub + Country!
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Property grounds

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (362)
"I recently stayed at this vacation rental and had a pleasant experience. The check-in process was simple. Just a heads-up, the drive to the house is a bit narrow in some spots, adding a touch of adventure to your journey! The property itself is well-maintained. The rooms are well-equipped, providing necessary amenities for a comfortable stay. The kitchen is functional with basic appliances and essentials, making meal preparation convenient. The views from the living area and front bedrooms are...
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
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: Nostalgia Lane in the heart of the city: Situated in Winchester, 12.4 mi/20 km from the heart of Middletown. Cozy studio close to Skyline Drive, Hiking, and Main Street.: Located 9.2 mi/14.8 km away in Front Royal. Apple Mountain Retreat: It’s situated in Linden, 11.6 mi/18.7 km away. Includes free WiFi, private patios, and Smart TVs. The Queen of Winchester Three Bedroom with Upper Level Deck: 13.2 mi/21.2 km away in Winchester. Amenities include private patios. Cozy English Basement Apt quiet but close to downtown: It’s situated in Winchester, 12.2 mi/19.6 km from Middletown.
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.