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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Apartments in Middletown

Pretty Little Apt by the Train II
Interior

Pretty Little Apt by the Train II

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great time. Love this city"
The price is AED 477
AED 803 total
includes taxes & fees
6 Oct - 7 Oct
Pretty Little Apt by the Train II
Cozy English Basement Apt quiet but close to downtown
Exterior

Cozy English Basement Apt quiet but close to downtown

9.6 out of 10, Exceptional, (7)
"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 367
AED 645 total
includes taxes & fees
20 Oct - 21 Oct
Cozy English Basement Apt quiet but close to downtown
Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Private kitchen

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester

2.0 star property
The price is AED 569
AED 953 total
includes taxes & fees
6 Oct - 7 Oct
Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
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)
"Great property with all the comforts of home"
The price is AED 654
AED 1,169 total
includes taxes & fees
21 Oct - 22 Oct
Morocco Loft 2BR overlooking city walking mall
Apple Mountain Retreat
Property grounds

Apple Mountain Retreat

10.0 out of 10, Exceptional, (18)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is AED 496
AED 855 total
includes taxes & fees
6 Oct - 7 Oct
Apple Mountain Retreat
Rosamond nice downtown studio apt
Interior

Rosamond nice downtown studio apt

8.0 out of 10, Very Good, (2)
"Small but appropriately priced."
The price is AED 404
AED 707 total
includes taxes & fees
6 Oct - 7 Oct
Rosamond nice downtown studio apt
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, (12)
"It was an amazing place, will recommend to friends and hopefully will be back."
The price is AED 557
AED 921 total
includes taxes & fees
7 Oct - 8 Oct
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath
1 bedroom, WiFi, bed sheets

Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath

1.0 star property
7.4 out of 10, Good, (3)
"Great Experience!"
The price is AED 977
AED 1,504 total
includes taxes & fees
28 Oct - 29 Oct
Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath
Skyland Hideaway | Mountain Cabin w/ Hot Tub
TV, fireplace, offices

Skyland Hideaway | Mountain Cabin w/ Hot Tub

10.0 out of 10, Exceptional, (14)
"We just stayed at SkyLand The house was clean, comfortable and welcoming. Matt is a great host Very responsive. The hot tub needed more water...no big deal. The beds were comfy and the coffee much appreciated upon arrival. Definitely wanna stay again."
The price is AED 522
AED 1,313 total
includes taxes & fees
22 Oct - 23 Oct
Skyland Hideaway | Mountain Cabin w/ Hot Tub
The Blue Door steps from Handley Library
Exterior detail

The Blue Door steps from Handley Library

2.0 star property
7.0 out of 10, Good, (2)
"Perfect. Met all expectations. Small but Great."
The price is AED 422
AED 707 total
includes taxes & fees
4 Nov - 5 Nov
The Blue Door steps from Handley Library
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
2 bedrooms, travel crib, WiFi, bed sheets

NEW! Historic Schoolhouse HotTub+FirePit+Wineries

The price is AED 356
AED 1,216 total
includes taxes & fees
6 Oct - 7 Oct
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Luxe Dome w Hot Tub, King Bed, Full Bath & FirePit
Terrace/patio

Luxe Dome w Hot Tub, King Bed, Full Bath & FirePit

9.4 out of 10, Exceptional, (3)
"This property was really cool to stay at. Nice and cozy with everything needed for a comfortable stay. "
The price is AED 678
AED 1,235 total
includes taxes & fees
7 Oct - 8 Oct
Luxe Dome w Hot Tub, King Bed, Full Bath & FirePit
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, (7)
"Perfect location and fit! Perfect balance of privacy and access"
The price is AED 662
AED 1,058 total
includes taxes & fees
6 Oct - 7 Oct
Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Private kitchen

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
12 Oct - 13 Oct
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Nostalgia Lane in the heart of the city
3 bedrooms, iron/ironing board, WiFi, bed sheets

Nostalgia Lane in the heart of the city

9.0 out of 10, Wonderful, (12)
"Great location in the heart of Winchester. Walking distance to everything. "
The price is AED 680
AED 1,203 total
includes taxes & fees
15 Oct - 16 Oct
Nostalgia Lane in the heart of the city
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Dining

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

9.0 out of 10, Wonderful, (6)
"Our Wonder Clock stay was great. Everything was as expected. Location to downtown was awesome and very easily walkable. Our stay was cut short unexpectedly, but we would stay here again! The host was very responsive to one concern we had and was willing to fix immediately. "
The price is AED 753
AED 1,382 total
includes taxes & fees
6 Oct - 7 Oct
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Scarborough Fair walk to downtown two story apt
Terrace/patio

Scarborough Fair walk to downtown two story apt

9.6 out of 10, Exceptional, (4)
"Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. "
The price is AED 815
AED 1,436 total
includes taxes & fees
6 Oct - 7 Oct
Scarborough Fair walk to downtown two story apt
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Exterior

The Foxwood Cabin | Hot Tub, Screened Porch, Grill

10.0 out of 10, Exceptional, (5)
"Our stay was positively excellent. The property was extremely well-kept and clean. The king bed was so comfortable, and the master bedroom was magical. The hot tub was the icing on the cake, and the views were stunning. I would recommend this property to anyone looking to get away from the hustle and bustle of every day living."
The price is AED 628
AED 1,572 total
includes taxes & fees
15 Oct - 16 Oct
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Microwave, oven, stovetop, dishwasher

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

The price is AED 808
AED 1,427 total
includes taxes & fees
6 Oct - 7 Oct
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Luxe Dome w/ Hot Tub, Full Bath & Mountain View!
1 bedroom, WiFi, bed sheets

Luxe Dome w/ Hot Tub, Full Bath & Mountain View!

10.0 out of 10, Exceptional, (4)
"Fabulous, will visit again"
The price is AED 937
AED 1,418 total
includes taxes & fees
5 Nov - 6 Nov
Luxe Dome w/ Hot Tub, Full Bath & 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.
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Top Middletown Hotel Reviews

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

10/10 Excellent
"Clean and inviting!!! Loved the cookie snack! "
Terry 1-night trip
Posted 2 days ago
Hampton Inn Winchester-University/Mall Area

Frequently asked questions

What's it like to stay at an apartment in Middletown?
You might not have many choices centrally in Middletown, but Expedia can help you find accommodations in the area similar to apartments. 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: Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks: Located in Rileyville, 16.4 mi/26.4 km from the heart of Middletown. Includes private balconies and sofa beds. Access to a hot tub is available on site. Secluded Cabin Escape • Hot Tub & Games • 13 Acres: Located 6 mi/9.7 km away in Strasburg. Private balconies and fireplaces are included. Onsite laundry facilities and a hot tub are on site. Apple Mountain Retreat: Located in Linden, 11.6 mi/18.7 km away. Includes free WiFi, private patios, and fireplaces. Access to onsite laundry facilities is available on site. New - Modern Mountain Retreat w/ Hot tub and view!: Located 13.2 mi/21.2 km away in Front Royal. Free WiFi, private balconies, and fireplaces are included. Onsite laundry facilities and a hot tub are on site. Whitetail Cabin | Couple`s Retreat w/ Hot Tub: Located in Linden, 12.3 mi/19.8 km from Middletown. Includes laundry facilities, private balconies, and fireplaces. Onsite laundry facilities and a hot tub are 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, 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.