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Check prices for these dates

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22 Aug - 24 Aug
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29 Aug - 31 Aug
In one month
12 Sep - 14 Sep
In two months
10 Oct - 12 Oct

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 SAR 488
SAR 808 total
includes taxes & fees
16 Sep - 17 Sep
Pretty Little Apt by the Train II
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 SAR 578
SAR 998 total
includes taxes & fees
3 Sep - 4 Sep
Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath
The Stock Exchange downtown 3rd floor studio apt
Fridge, microwave, oven, stovetop

The Stock Exchange downtown 3rd floor studio apt

2.0 star property
6.0 out of 10, (1)
The Stock Exchange downtown 3rd floor studio apt
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 SAR 432
SAR 723 total
includes taxes & fees
1 Sep - 2 Sep
The Blue Door steps from Handley Library
Rosamond nice downtown studio apt
Interior

Rosamond nice downtown studio apt

8.0 out of 10, Very Good, (2)
"Small but appropriately priced."
Rosamond nice downtown studio apt
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Fridge, microwave, oven, stovetop

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

2.0 star property
8.0 out of 10, Very Good, (3)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
The price is SAR 518
SAR 876 total
includes taxes & fees
17 Aug - 18 Aug
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
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, (10)
"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 SAR 759
SAR 1,149 total
includes taxes & fees
15 Sep - 16 Sep
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Berryville Bliss: Basement Apartment in welcoming Berryville
Outdoor dining

Berryville Bliss: Basement Apartment in welcoming Berryville

10.0 out of 10, Exceptional, (3)
"Clean, comfortable and close to Historic Rosemont! Pool was incredible!"
The price is SAR 679
SAR 1,715 total
includes taxes & fees
26 Aug - 27 Aug
Berryville Bliss: Basement Apartment in welcoming Berryville
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, (5)
"Perfect location and fit! Perfect balance of privacy and access"
Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks
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 SAR 705
SAR 1,134 total
includes taxes & fees
17 Aug - 18 Aug
Luxe Dome w/ Hot Tub, Full Bath & Mountain View!
Apple Mountain Retreat
Property grounds

Apple Mountain Retreat

10.0 out of 10, Exceptional, (14)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is SAR 507
SAR 873 total
includes taxes & fees
17 Aug - 18 Aug
Apple Mountain Retreat
Nostalgia Lane in the heart of the city
3 bedrooms, iron/ironing board, WiFi, bed sheets

Nostalgia Lane in the heart of the city

8.8 out of 10, Excellent, (10)
"Great location in the heart of Winchester. Walking distance to everything. "
Nostalgia Lane in the heart of the city
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 SAR 821
SAR 1,412 total
includes taxes & fees
3 Sep - 4 Sep
Luxe Dome w Hot Tub, King Bed, Full Bath & FirePit
Scarborough Fair walk to downtown two story apt
Terrace/patio

Scarborough Fair walk to downtown two story apt

9.4 out of 10, Exceptional, (3)
"We stayed here overnight after our trip to Shenandoah. House had everything we needed for a peaceful night. "
The price is SAR 833
SAR 1,471 total
includes taxes & fees
17 Aug - 18 Aug
Scarborough Fair walk to downtown two story apt
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"The front desk and cleaning staff were really helpful when we lost our car key fob. They offered to call mechanics to create a duplicate and finally even found our lost one. "
Sandip 2-night trip
Posted 1 day ago
Comfort Inn & Suites Winchester

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 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. Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks: Located in Rileyville, 16.4 mi/26.3 km away. Includes private balconies and sofa beds. Access to a hot tub is available on site. Berryville Bliss: Basement Apartment in welcoming Berryville: Located 17.9 mi/28.9 km away in Berryville. A private pool, free WiFi, and private patios are included. An outdoor pool and a hot tub are on site. Apple Mountain Retreat: Located in Linden, 11.6 mi/18.7 km from Middletown. Includes free WiFi, private patios, and fireplaces. 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, 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.