A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Middletown apartments

A living room with a dining table, two sofas, a floor lamp, a clock, and a window with curtains.

1. Downtown Apt 3 • 2BR • Near Park & River • Private

Downtown Apt 3 • 2BR • Near Park & River • Private
Front Royal
10.0 out of 10, Exceptional, (1 review)
"This property is absolutely perfect: great location for walking through the historic part of town, close to food & fun, very well appointed (right down to quality toilet paper!) & perfectly clean. Yuliya responded very quickly from the moment I made the reservation to checkout. We would stay again for sure! Thank you, Yuliya & Mark!"
United States
kim B.
The price is CA $204
CA $376 total
includes taxes & fees
Oct 29 - Oct 30
Downtown Apt 3 • 2BR • Near Park & River • Private
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

2. The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 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 $105
CA $350 total
includes taxes & fees
Oct 29 - Oct 30
The Queen of Winchester Three Bedroom with Upper Level Deck
A black door with the number 415, a window, and a hanging flower basket.

3. Downtown Apt.1 • 2BR/2BA• Near Park/River• Private

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
The price is CA $212
CA $405 total
includes taxes & fees
Oct 29 - Oct 30
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

4. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.8 out of 10, Excellent, (3 reviews)
"Easy space for a 2 person weekend getaway, very close within walking distance to food, shops, breweries, etc"
United States
Jameson D.
The price is CA $155
CA $274 total
includes taxes & fees
Nov 12 - Nov 13
Rosamond nice downtown studio apt
A living room with a sofa, ottoman, lamp, and a mirror.

5. Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is CA $225
CA $427 total
includes taxes & fees
Oct 29 - Oct 30
Morocco Loft 2BR overlooking city walking mall
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

6. 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
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

7. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
The price is CA $208
CA $369 total
includes taxes & fees
Nov 23 - Nov 24
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

8. 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
8.4 out of 10, Very good, (6 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
United States
Leslie L.
The price is CA $193
CA $332 total
includes taxes & fees
Nov 15 - Nov 16
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A room with a radiator, a wooden rocking chair, a door, and a window with a lace curtain.

9. The Blue Door steps from Handley Library

The Blue Door steps from Handley Library
Old Town Winchester
5.4 out of 10, (3 reviews)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The price is CA $161
CA $270 total
includes taxes & fees
Oct 29 - Oct 30
The Blue Door steps from Handley Library
A living room with a fireplace, a television mounted above it, and a large window with a view of trees.

10. NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
9.4 out of 10, Exceptional, (3 reviews)
"We were staying at the schoolhouse to go hiking and ride bikes. They house has been tastefully decorated. I enjoyed the quite community and the listening to the tree frogs at night. Front Royal has a few things you can enjoy such as the movie theatre, bakery and state park. I would highly recommend this propery."
United States
Suzanne J.
The price is CA $133
CA $450 total
includes taxes & fees
Nov 16 - Nov 17
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

11. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (15 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is CA $273
CA $491 total
includes taxes & fees
Oct 29 - Oct 30
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a table and chairs.

12. Downtown Apt 2 • 2BR • Near Park & River • Private

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
The price is CA $204
CA $403 total
includes taxes & fees
Oct 29 - Oct 30
Downtown Apt 2 • 2BR • Near Park & River • Private
A building with a red door, white trim, and a small balcony with a metal railing.

13. The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
United States
Greg A.
The price is CA $154
CA $281 total
includes taxes & fees
Nov 12 - Nov 13
The Stock Exchange downtown 3rd floor studio apt
A wooden deck leading to a building with a sign reading "TURKEY RUN".

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

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Luray
9.6 out of 10, Exceptional, (24 reviews)
"Great location for access to Shenandoah and Luray. The cabin was very nice and clean and it was a perfect solo getaway!"
United States
Kelsie H.
The price is CA $240
CA $505 total
includes taxes & fees
Nov 9 - Nov 10
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
A living room with a sofa, armchair, coffee table, and a television.

15. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
8.8 out of 10, Excellent, (21 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is CA $259
CA $472 total
includes taxes & fees
Oct 29 - Oct 30
Nostalgia Lane in the heart of the city
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

16. 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
9.0 out of 10, Wonderful, (10 reviews)
"Great location…"
United States
John P.
The price is CA $287
CA $527 total
includes taxes & fees
Oct 29 - Oct 30
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A balcony with a table, two wine glasses, and a view of a fenced area with a truck and a building in the background.

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

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
9.6 out of 10, Exceptional, (5 reviews)
"Such a lovely stay. The property was peaceful and relaxing, and the night sky was absolutely beautiful. We loved our time here and would happily return. Great communication (and snacks) too :)"
United States
Melissa B.
The price is CA $304
CA $373 total
includes taxes & fees
Nov 1 - Nov 2
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A wooden deck with a bench and a grill, overlooking a forested area.

18. 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, (11 reviews)
"Absolutely loved this tiny cabin. So relaxing to be near the river and the hot tub is a great add in! Will definitely stay here again!"
United States
Anonymous traveller
The price is CA $333
CA $608 total
includes taxes & fees
Nov 16 - Nov 17
Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks
A hot tub with a wooden deck and a tented accommodation.

19. Glamping dome w/ hot tub & mountain views

Glamping dome w/ hot tub & mountain views
Augusta
9.6 out of 10, Exceptional, (10 reviews)
"Wonderful stay! Will be back! "
United States
Shanna A.
The price is CA $335
CA $645 total
includes taxes & fees
Nov 3 - Nov 4
Glamping dome w/ hot tub & mountain views
A geodesic dome tent with a wooden deck and red chairs.

20. 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 CA $397
CA $707 total
includes taxes & fees
Nov 17 - Nov 18
Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath
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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Rapport qualité prix le meilleur"
michel 1-night trip
Posted 3 hours ago
Quality Inn Winchester

Find out more about Middletown

Middletown Apartments information

Number of reviews
109
Accommodation
53 Apartments
Lowest Price
CA $270
Highest Price
CA $707

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: Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC: Located 12.6 mi/20.2 km away in Winchester. Glamping dome w/ hot tub & mountain views: Located in Augusta, 22.6 mi/36.4 km away. Includes private balconies. Access to a hot tub 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. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!: It's situated in Winchester, 12.7 mi/20.5 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. 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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