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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Apartments in Middletown

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 SAR 581
SAR 959 total
includes taxes & fees
7 Oct - 8 Oct
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
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 SAR 506
SAR 873 total
includes taxes & fees
15 Oct - 16 Oct
Apple Mountain Retreat
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 SAR 833
SAR 1,483 total
includes taxes & fees
27 Oct - 28 Oct
Scarborough Fair walk to downtown two story apt
Charming Loft In Winchester Va, Furnished and all Inclusive
Living area

Charming Loft In Winchester Va, Furnished and all Inclusive

8.0 out of 10, Very Good, (4)
"Nice property, everything works well. It's a perfect space for two people. If you're looking to explore the city and just come back to relax, it's a good option for you."
Charming Loft In Winchester Va, Furnished and all Inclusive
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 SAR 694
SAR 1,258 total
includes taxes & fees
27 Oct - 28 Oct
Nostalgia Lane in the heart of the city
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 SAR 413
SAR 722 total
includes taxes & fees
5 Oct - 6 Oct
Rosamond nice downtown studio apt
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 SAR 668
SAR 1,194 total
includes taxes & fees
21 Oct - 22 Oct
Morocco Loft 2BR overlooking city walking mall
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 Blue Door steps from Handley Library
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 812 total
includes taxes & fees
5 Oct - 6 Oct
Pretty Little Apt by the Train II
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 SAR 701
SAR 1,112 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 SAR 638
SAR 806 total
includes taxes & fees
9 Oct - 10 Oct
Cozy studio close to Skyline Drive, Hiking, and Main Street.
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 star property
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
New - Modern Mountain Retreat w/ Hot tub and view!
5 bedrooms, desk, iron/ironing board, travel crib

New - Modern Mountain Retreat w/ Hot tub and view!

10.0 out of 10, Exceptional, (22)
"We loved this property and will likely return for another visit."
New - Modern Mountain Retreat w/ Hot tub and view!
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 1,002
SAR 1,506 total
includes taxes & fees
23 Oct - 24 Oct
Luxe Dome w/ Hot Tub, Full Bath & Mountain View!
Waterfront Virginia Retreat w/ Canoe, Pets Welcome
Apartment (0 Bedroom) | Front of property

Waterfront Virginia Retreat w/ Canoe, Pets Welcome

3.0 star property
10.0 out of 10, Exceptional, (2)
Waterfront Virginia Retreat w/ Canoe, Pets Welcome
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."
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
The Queen of Winchester Three Bedroom with Upper Level Deck
Private kitchen

The Queen of Winchester Three Bedroom with Upper Level Deck

7.8 out of 10, Good, (7)
"Very comfortable. Close to all the things we wanted to do!Owner responded quickly to small issue and was super helpful!"
The Queen of Winchester Three Bedroom with Upper Level Deck
Front Royal Retreat on 3 Acres w/ Mtn Views!
Apartment (2 Bedrooms) | Interior

Front Royal Retreat on 3 Acres w/ Mtn Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"What a lovely quiet place to stay! An excellent house, much better option than a hotel for my family. "
Front Royal Retreat on 3 Acres w/ Mtn Views!
King Apartment -2 miles to I-81
1 bedroom, desk, cribs/infant beds, free WiFi

King Apartment -2 miles to I-81

10.0 out of 10, Exceptional, (11)
"Nicely appointed, very comfortable and exceptionally clean. We would stay here again! The owners are very thoughtful with the details and include items like snacks and a make up mirror that isn't typically included. Great spot and very reasonably priced."
King Apartment -2 miles to I-81
The Outpost Suite 3 - Whimsical Farmhouse Retreat
Outdoor dining

The Outpost Suite 3 - Whimsical Farmhouse Retreat

7.2 out of 10, Good, (10)
"First we found it strange that you enter into this unit through the bathroom. It is up a laneway behind a house and backs onto a subdivision. The “kitchenette” was not very clean with some leftover packages of food in drawer from previous guests and no microwave. It was a warm day when we arrived and the heat was on full blast and was controlled from another unit. It continued to blast heat for our whole visit. We were to stay for 3 nights and the first night was fine as there were no guests in...
The Outpost Suite 3 - Whimsical Farmhouse Retreat
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
"Very nice property. "
Pam 1-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 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. Apple Mountain Retreat: Located 11.6 mi/18.7 km away in Linden. Free WiFi, private patios, and fireplaces are included. Access to onsite laundry facilities 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. 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. Charming Loft In Winchester Va, Furnished and all Inclusive: It's situated in Winchester, 9.5 mi/15.3 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. 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.