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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Middletown apartments

Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (23 reviews)
"Great place to stayed "
United States
Mike F.
The price is CA $184
CA $316 total
includes taxes & fees
May 1 - May 2
Apple Mountain Retreat
Interior

Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."
United States
Stephanie L.
The price is CA $177
CA $298 total
includes taxes & fees
May 4 - May 5
Pretty Little Apt by the Train II
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 CA $252
CA $454 total
includes taxes & fees
May 4 - May 5
Nostalgia Lane in the heart of the city
Interior

Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is CA $150
CA $262 total
includes taxes & fees
Apr 30 - May 1
Rosamond nice downtown studio apt
Living area

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 CA $243
CA $445 total
includes taxes & fees
Apr 30 - May 1
Morocco Loft 2BR overlooking city walking mall
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 CA $128
CA $283 total
includes taxes & fees
May 4 - May 5
The Queen of Winchester Three Bedroom with Upper Level Deck
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 CA $123
CA $392 total
includes taxes & fees
Apr 30 - May 1
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
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 CA $209
CA $343 total
includes taxes & fees
May 3 - May 4
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
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, (7 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 traveller
The price is CA $136
CA $239 total
includes taxes & fees
May 25 - May 26
Cozy English Basement Apt quiet but close to downtown
Interior

Very charming & spacious 2 bedrm

Very charming & spacious 2 bedrm
Winchester
Very charming & spacious 2 bedrm
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 CA $150
CA $272 total
includes taxes & fees
May 4 - May 5
The Stock Exchange downtown 3rd floor studio apt
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
8.6 out of 10, Excellent, (4 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is CA $188
CA $320 total
includes taxes & fees
May 4 - May 5
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
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.
The price is CA $279
CA $509 total
includes taxes & fees
Apr 30 - May 1
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
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, (6 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 CA $302
CA $540 total
includes taxes & fees
Apr 30 - May 1
Scarborough Fair walk to downtown two story apt
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, (4 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is CA $266
CA $492 total
includes taxes & fees
Apr 30 - May 1
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
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, (8 reviews)
"We had a wonderful time, loved the location and space! "
United States
Jennifer C.
The price is CA $260
CA $412 total
includes taxes & fees
May 20 - May 21
Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks
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 CA $296
CA $352 total
includes taxes & fees
Apr 30 - May 1
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
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.
The price is CA $199
CA $352 total
includes taxes & fees
May 4 - May 5
Yellow Submarine trendy basement apt and courtyard
Room

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Old Town Winchester
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Outdoor spa tub

Glamping dome w/hot tub & fire pit

Glamping dome w/hot tub & fire pit
Augusta
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful stay!"
United States
Eli W.
The price is CA $272
CA $432 total
includes taxes & fees
Apr 30 - May 1
Glamping dome w/hot tub & fire pit
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
"Staff and property was great"
Preston 1-night trip
Posted 5 hours ago
Comfort Inn & Suites Winchester

Find out more about Middletown

Middletown Apartments information

Number of reviews
118
Accommodation
51 Apartments
Lowest Price
CA $239
Highest Price
CA $540

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. WonderClock House downtown vintage duplex w/ porches, steps to Handley Library: 12.6 mi/20.2 km away in Winchester. Fireplaces and Smart TVs are included. Nostalgia Lane in the heart of the city: Located in Winchester, 12.4 mi/20 km from Middletown. Includes Smart TVs. 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 lovely local spots to get outside and enjoy nature. 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.

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