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Top Holiday Rentals in Middletown

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

10.0 out of 10, Exceptional, (328)
"This cabin fulfilled all my needs. Simple, clean, and efficient. The location was secluded and quiet, just what I needed. Will definitely return!"
The price is £221
includes taxes & fees
8 Jul - 9 Jul
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

9.6 out of 10, Exceptional, (181)
"We had an extremely relaxing stay. The area is gorgeous…loved being close to the water. We brought our dog and it was great to let him run and play and just be a dog. Did have a few issues with a few appliances, but the host was super quick to bring a new remote and coffee pot. All in all we would stay again!"
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Cabin near River, Firepit, Family-friendly, WiFi, Great Location, Veteran owned!

10.0 out of 10, Exceptional, (31)
"The house is great! We loved our stay. The place is even better than the listing. Know that you’re not particularly close to any restaurants or stores but that wasn’t an issue for us. You’re close to the park entrance. The lot is peaceful and an amazing place to unwind after a long day of hiking. "
Cabin near River, Firepit, Family-friendly, WiFi, Great Location, Veteran owned!

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (320)
"We had a wonderful time enjoying this peaceful setting. The house is just as described and everything worked well! "
Star view cabin-Riverfront

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

9.8 out of 10, Exceptional, (291)
"We spent two night, and the place was wonderful. The views of the mountains are magical. The location is great, and close to so many attractions. Highly recommend a visit here."
The price is £212
includes taxes & fees
1 Jul - 2 Jul
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

10.0 out of 10, Exceptional, (318)
"My wife & I needed a break from the daily grind & this place was exactly what the doctor ordered. Highly highly recommend this place to anyone. We hope to be able to return again sometime"
The price is £221
includes taxes & fees
9 Jul - 10 Jul
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Lookout Cabin in the mountains, Amazing Views!

10.0 out of 10, Exceptional, (14)
"Perfect for a night away. Can’t beat the views. Host was wonderful and very quick to reply throughout whole process! Would definitely book again. "
The price is £257
includes taxes & fees
1 Jul - 2 Jul
Lookout Cabin in the mountains, Amazing Views!

Falling Leaf Cabin - Rustic Charm With Modern Decor!

9.8 out of 10, Exceptional, (287)
"Exceeded expectations."
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi

9.8 out of 10, Exceptional, (55)
"The cabin is very nice with great location. We enjoyed our time there."
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (86)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (152)
"We had a wonderful stay! Cabin was clean and welcoming, beautiful views, and overall a charming, relaxing cabin in the woods!"
Secluded River Cabin Getaway (Masten Cabin)

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

9.6 out of 10, Exceptional, (315)
"Beautiful cabin and spectacular location. Highly recommended for a great escape. Loved it!!!"
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

Beautiful Private Cabin, adjacent to the National Forest

9.8 out of 10, Exceptional, (127)
"Peaceful and wonderful. Well appointed and very clean"
Beautiful Private Cabin, adjacent to the National Forest

Heaven's Hideaway- perfect getaway near the river!

9.8 out of 10, Exceptional, (114)
"The cabin was clean, comfortable, and tastefully decorated. It offered lots of amenities, all of which were in working order. I would definitely recommend it for a weekend getaway!"
Heaven's Hideaway- perfect getaway near the river!

Westcott House- Privacy, amenities and space all in one beautiful package!

9.8 out of 10, Exceptional, (88)
"This was just what we needed. We had a family of 30. Included were teens that enjoyed having a separate space and pool table. The upstairs main room was so spacious and the tables were set up like a restaurant. Perfect for meals and mingling. The kitchen was well stocked for cooking meals. We would stay here again. "
Westcott House- Privacy, amenities and space all in one beautiful package!

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (185)
"We had such a wonderful time in this all accommodating, cozy, beautiful cabin! We caught trout in Paddy Creek that we brought back to the cabin and cooked for dinner. We hiked the trail behind the cabin through the national park. We relaxed!! A much needed getaway from the hustle and bustle!"
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

9.6 out of 10, Exceptional, (58)
"Family and I loved our stay at Whistling Woods Retreat! Relax by the fire and take in the blue ridge mountains! Short drive to luray and Shenandoah national park. Tons of games and places to explore on the property for the kids. Definitely Recommend ! "
The price is £250
includes taxes & fees
1 Jul - 2 Jul
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (43)
"The PERFECT stay! We came for the Upperville horse show and you cannot beat the location of this charming cottage. Close proximity to dining, grocery stores, wineries, horse show, and on a quiet street. William was an excellent host with attention to detail, thoughtfulness, and quick and responsive to any questions. "
Historical cottage in the town of Paris

Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating

9.0 out of 10, Wonderful, (27)
"location by the river was beautiful. House is roomy and great for our family of 12. "
The price is £567
includes taxes & fees
16 Jul - 17 Jul
Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating

Charming 3-bedroom cabin with Moutain Views, Hottub, WiFi in Shenandoah.

2.0 star property
10.0 out of 10, Exceptional, (18)
"We loved our stay at this property and Lauren was great to work with and responded to messages quickly. We loved being able to use the hot tub and have our own kitchen and separate bathrooms. "
The price is £285
includes taxes & fees
3 Jul - 4 Jul
Charming 3-bedroom cabin with Moutain Views, Hottub, WiFi in Shenandoah.
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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Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Middletown has to offer?

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly: This holiday home rental outside of Middletown is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middletown?

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

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 holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.