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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for Middletown apartments

Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (24 reviews)
"Great place to stayed "
United States
Mike F.
The price is SAR 507
SAR 877 total
includes taxes & fees
28 May - 29 May
Apple Mountain Retreat
Terrace/patio

Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (8 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveler
The price is SAR 450
SAR 748 total
includes taxes & fees
30 May - 31 May
Cozy English Basement Apt quiet but close to downtown
Interior

NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
8.0 out of 10, Very Good, (1 review)
"The listing indicated pets were welcome and we were able to bring our 13 year old dog, who loves traveling with my husband and I. There was some initial confusion after we booked the Schoolhouse, saying pets are prohibited. Through contact with the host, it was cleared up pretty quickly. All in all, the place was comfortable and we had what we needed to cook a couple of meals. I loved the area and enjoyed walking our dog on the state-maintained back roads. We would have liked to take advantage...
United States
Kathy S.
The price is SAR 338
SAR 1,164 total
includes taxes & fees
25 May - 26 May
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fridge, microwave, oven, stovetop

The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.8 out of 10, Good, (7 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is SAR 473
SAR 913 total
includes taxes & fees
22 Jun - 23 Jun
The Queen of Winchester Three Bedroom with Upper Level Deck
Terrace/patio

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

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Luray
9.8 out of 10, Exceptional, (18 reviews)
"It was an amazing place, will recommend to friends and hopefully will be back."
United States
Lucerito I.
The price is SAR 684
SAR 1,088 total
includes taxes & fees
27 May - 28 May
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Terrace/patio

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

Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks
Luray
10.0 out of 10, Exceptional, (9 reviews)
"We had a wonderful time, loved the location and space! "
United States
Jennifer C.
The price is SAR 625
SAR 1,003 total
includes taxes & fees
3 Jun - 4 Jun
Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks
2 bedrooms, iron/ironing board, WiFi, bed sheets

Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is SAR 668
SAR 1,203 total
includes taxes & fees
22 Jun - 23 Jun
Morocco Loft 2BR overlooking city walking mall
Smart TV

Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.0 out of 10, Wonderful, (16 reviews)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is SAR 694
SAR 1,203 total
includes taxes & fees
21 Jun - 22 Jun
Nostalgia Lane in the heart of the city
Smart TV, books

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

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is SAR 518
SAR 863 total
includes taxes & fees
22 Jun - 23 Jun
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Interior

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

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Old Town Winchester
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful space; helpful host."
United States
Sally C.
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Smart TV

Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4 reviews)
"You need to add some kitchen tongs Otherwise everything was fantastic!!!"
United States
Michelle K.
Yellow Submarine trendy basement apt and courtyard
Terrace/patio

Glamping dome w/ hot tub & mountain views

Glamping dome w/ hot tub & mountain views
Augusta
9.6 out of 10, Exceptional, (7 reviews)
"This property was really cool to stay at. Nice and cozy with everything needed for a comfortable stay. "
United States
Brandy B.
The price is SAR 904
SAR 1,386 total
includes taxes & fees
21 Jun - 22 Jun
Glamping dome w/ hot tub & mountain views
Property grounds

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
10.0 out of 10, Exceptional, (1 review)
"Kay and Joe are wonderful guests. They went above and beyond to made us feel so welcomed. The Love Nest is the most cozy and wonderful place we stayed in. Their property is gorgeous and very peaceful. Everything we needed to unwind from a hard week. We will be coming back soon!"
United States
Mariana F.
The price is SAR 814
SAR 962 total
includes taxes & fees
25 May - 26 May
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Dining

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

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.2 out of 10, Wonderful, (7 reviews)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Exterior detail

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
6.0 out of 10, (1 review)
The price is SAR 413
SAR 744 total
includes taxes & fees
22 Jun - 23 Jun
The Stock Exchange downtown 3rd floor studio apt
Smart TV, fireplace

Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"Excellent location, easy walk to most of the Old Town area. Michele is a great host, will definitely stay here again if in the area. "
United States
Larry E.
The price is SAR 833
SAR 1,488 total
includes taxes & fees
21 Jun - 22 Jun
Scarborough Fair walk to downtown two story apt
Terrace/patio

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

Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath
Augusta
7.4 out of 10, Good, (3 reviews)
"Great Experience!"
United States
Kimberly B.
The price is SAR 675
SAR 1,133 total
includes taxes & fees
2 Jun - 3 Jun
Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath
Outdoor spa tub

Glamping dome w/ hot tub & mountain views

Glamping dome w/ hot tub & mountain views
Augusta
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful stay!"
United States
Eli W.
The price is SAR 782
SAR 1,218 total
includes taxes & fees
3 Jun - 4 Jun
Glamping dome w/ hot tub & mountain views
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

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

6/10 Okay
"Food was great. Room was ok. But we didnt have any internet access. Our room was a black hole. The room next had internet. But not us. They gave us a number to a tech guy but after an hour there was still no solution. We were not offered a different room until we complained at check-out to a different staff member.. too little.. too late"
Laura 1-night trip
Posted 3 hours ago
Holiday Inn Express Woodstock-Shenandoah Valley by IHG

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. 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. Nostalgia Lane in the heart of the city: Located 12.4 mi/20 km away in Winchester. Amenities include Smart TVs. 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 from Middletown. Includes private balconies and sofa beds. Access to a hot tub 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. Shenandoah River and Cedar Creek and Belle Grove National Historical Park are a couple of lovely local spots to get outside and enjoy nature. While here, Belle Grove Plantation and Jackson's Chase Golf Course 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.

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