Middletown Vacation Rentals from ￥13,436: Search Short-Term Rentals

Q: What are some of the best vacation home rentals that Middletown has to offer?

Secluded River Cabin Getaway (Masten Cabin) : This vacation home rental near Middletown is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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Vacation Rentals in Middletown

￥54,067 total

includes taxes & fees

Jul 13 - Jul 14

"Everything was as described. We had a lovely weekend relaxing under the stars in the hot tub and spending time with family in the Shenandoah Valley. We can't wait to come back to this oasis!"

￥44,527 total

includes taxes & fees

Jul 1 - Jul 2

￥101,197 total

includes taxes & fees

Jul 13 - Jul 14

"Our family stayed one night on the way home from vacation. The cabin was a great place to access the National Park and caves! It was well furnished and had everything we needed! "

￥53,477 total

includes taxes & fees

Jul 8 - Jul 9

"Mint Cottage is a gem. Its spacious, beautifully furnished, and a great place to stay to explore Shenandoah National Park and its environs"

￥69,066 total

includes taxes & fees

Jul 7 - Jul 8

"The place is amazing and the host was quick with the response! Me and my family had a great time and will be returning guests!!!"

￥208,445 total

includes taxes & fees

Jun 26 - Jun 27

"Great stay and very accommodating for outings/get together with friends. We loved the fire pit area. Great views of the Shenandoah river as well."

￥62,687 total

includes taxes & fees

Jul 20 - Jul 21

"Very clean.. Great location! "

￥22,393 total

includes taxes & fees

Jun 30 - Jul 1

"Great proximity to Shenandoah N P ! Comfortable beds! Appreciated the host let us check in early."

￥59,600 total

includes taxes & fees

Jul 15 - Jul 16

"Wonderful stay. "

￥68,819 total

includes taxes & fees

Jul 7 - Jul 8

"Property is freshly renovated, very clean, nicely appointed. There was a pervasive musty/mildewy smell throughout the unit, i expect there is a leak somewhere from the renovation. Also, while well appointed, there were no hospitality items...usually there is at least coffee/tea, especially at this price point. We enjoyed our stay and the location was convenient to the theater and the downtown area."

￥51,071 total

includes taxes & fees

Jul 24 - Jul 25

"This was the perfect location for our little get away. We had Easter lunch, played games, and stayed in a very clean nice place!!"

￥37,059 total

includes taxes & fees

Jun 30 - Jul 1

"Really enjoyed our stay. The house was lovely with amazing views. The bar and game room were fun. Lots of detail and thought were put into making this house feel like home. We will definitely be back!"

￥114,010 total

includes taxes & fees

Jul 21 - Jul 22

"The cottage was very charming and outfitted for maximum relaxation. We would definitely stay there again."

￥46,841 total

includes taxes & fees

Jun 27 - Jun 28

"Very well maintained property. "

￥62,669 total

includes taxes & fees

Jul 2 - Jul 3

"Very well maintained, clean, gorgeous views. We'll be back next year."

￥52,055 total

includes taxes & fees

Jun 29 - Jun 30

"Beautiful mountain view! The trip was nice and beautiful! I love a good cozy vibe in the mountains! Communication with property manger was very excellent customer service! "

￥54,155 total

includes taxes & fees

Jun 26 - Jun 27

"This place is amazing! So clean and comfortable. Drive up to the cabin is very bumpy but so very worth it. "

￥53,654 total

includes taxes & fees

Jun 30 - Jul 1

"Hideaway cabin was the perfect mountain getaway. My husband and I stayed here with our two dogs and it was so cozy and had everything we needed. The cabin was clean, and had all the essentials for cooking. The views are amazing and we loved using the wood fire stove. We took our dogs to the waterfall hike and they had a blast. Definitely recommend staying here! "

￥54,155 total

includes taxes & fees

Jun 26 - Jun 27

"We loved this little getaway spot! The view was gorgeous and the cabin was so clean and cozy!"

￥54,155 total

includes taxes & fees

Jun 26 - Jun 27

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Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middletown!

Recent reviews of Middletown properties

Microtel Inn & Suites by Wyndham Winchester

5/5 Excellent

Great night stay

"Immaculate, very comfortable and attractive."

A verified traveler stayed at Microtel Inn & Suites by Wyndham Winchester

Posted 2 days ago

Holiday Inn Winchester Se-Historic Gateway by IHG

5/5 Excellent

"Our room was comfortable and had many amenities such as a refrigerator and microwave. The staff were welcoming and friendly. Although we were not happy that the restaurant was closed for dinner, the breakfast was wonderful. "

A verified traveler stayed at Holiday Inn Winchester Se-Historic Gateway by IHG

Posted 3 days ago

SpringHill Suites by Marriott Winchester

5/5 Excellent

"Overall, the stay was very nice clean room, comfortable bed, clean and soft sheets, and super nice shower! However, it would have been nice to be notified ahead of time of the parking lot paving and parking situation. The young lady at the front desk was very kind and helpful in telling us where we could park, but it was still a bit annoying. "

A verified traveler stayed at SpringHill Suites by Marriott Winchester

Posted 3 days ago

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, you can find vacation rentals near well known sights in Middletown, or you can go with a secluded option if you're looking for relaxation. Our travelers say Middletown has a good selection of bars and the restaurants. Make sure you have time to check out the entertainment choices and churches during your trip.

What are some of the best vacation home rentals that Middletown has to offer?

Secluded River Cabin Getaway (Masten Cabin): This vacation home rental near Middletown is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Middletown?

Choose from 3 Expedia vacation rentals in Middletown for a memorable vacation.

What’s there to see and do in Middletown?

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, Belle Grove Plantation and Cedar Creek Battlefield Foundation are other places worth a visit.

What’s a vacation rental in Middletown like?

Vacation rentals are private properties where you can stay for a couple of days or more in Middletown. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for small groups.

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Middletown Vacation Rentals

Check prices for these dates

Vacation Rentals in Middletown

Welcome to the Ladybug Retreat!

Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

LUX Mountain View - Hot tub, WiFi, AC

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

Mint Cottage at Little Washington - a modern, spacious retreat with a view

Pirate's Cove River Front Oasis, Group Adventure

Windy Knoll Adventure!

Juliana Spa Suite - Luxury Main Floor

Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

Big Sunny Family House

Cameron Charmer pristine downtown apt with double master suites

Cozy 2-bedroom condo in charming Stephens City

Sunset Haven - 10 min from Skyline Drive. Hot Tub

Newly renovated Farm cottage with Mountain views

River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi

Ridgeview Mountain Cabin

Overlook Mountain Cabin

Shenandoah Mountain Cabin

Hideaway Mountain Cabin

Sunset Mountain Cabin

Find out more about Middletown

Recent reviews of Middletown properties

Microtel Inn & Suites by Wyndham Winchester

Comfort Inn Woodstock Shenandoah

Quality Inn

Sleep Inn & Suites

Hampton Inn Winchester N/Conference Center, VA

Comfort Inn & Suites

Holiday Inn Winchester Se-Historic Gateway by IHG

SpringHill Suites by Marriott Winchester

Country Inn & Suites by Radisson, Winchester, VA

Frequently asked questions