Photo by Stephanie Sutton

Middletown Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Middletown

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (321)
"We thoroughly enjoyed our stay here. From the moment you walk into the cabin, the views are spectacular and the surroundings are relaxing. We had a wonderful time and can’t wait to come back in the warmer weather to enjoy the outdoors more within a quick drive of lots of parks and scenic views Very clean and well appointed top-notch. "
Star view cabin-Riverfront

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

10.0 out of 10, Exceptional, (330)
"The property was on a beautiful valley right next to the Shenandoah river. Everything was about as perfect as it could be. Would definitely recommend. "
The price is CA $240
CA $403 total
includes taxes & fees
Jul 20 - Jul 21
"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, (184)
"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

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

9.8 out of 10, Exceptional, (292)
"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 CA $216
CA $373 total
includes taxes & fees
Jul 13 - Jul 14
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

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.

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

10.0 out of 10, Exceptional, (32)
"We came for our honeymoon and had a great time. Thanks!"
Cabin near River, Firepit, Family-friendly, WiFi, Great Location, Veteran owned!

Lookout Cabin in the mountains, Amazing Views!

10.0 out of 10, Exceptional, (14)
"A small, quaint, mountain-top cabin close to Shenandoah National Park. The cabin was clean and cozy with all the amenities you need. Beautiful view from the living room and outdoor hot tub. "
The price is CA $257
CA $481 total
includes taxes & fees
Jul 20 - Jul 21
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!

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (156)
"It was clean. It had a beautiful drive to it and it was tucked up in the woods. It would be nice if there was curtains, but that is OK. You are surrounded by trees. Enjoyed our visit. Has a very cute town nearby. Wasn’t in the house very much was enjoying all the scenery."
Secluded River Cabin Getaway (Masten Cabin)

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

9.8 out of 10, Exceptional, (58)
"The cabin is very nice with great location. We enjoyed our time there."
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi

Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing

10.0 out of 10, Exceptional, (1)
"Our stay at Bala’s home was wonderful. The location right on the river is perfect for a relaxing getaway. A very close drive to the National Park and Front Royal. The home is updated nicely and amenities are well stocked, above average kitchen supplies from the typical vacation rental. Do note that there are no tvs in the bedrooms which we appreciated but some may not. Overall it was great. "
Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing

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

10.0 out of 10, Exceptional, (319)
"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 CA $253
CA $417 total
includes taxes & fees
Jul 22 - Jul 23
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

10.0 out of 10, Exceptional, (44)
"Great getaway location. Beautiful property"
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (177)
"Private and cute cottage in the woods. Shenandoah valley is beautiful!"
Secluded, Cozy Cottage in the Shenandoah Valley

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

9.6 out of 10, Exceptional, (319)
"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

Heaven's Hideaway- perfect getaway near the river!

9.8 out of 10, Exceptional, (115)
"Nice peaceful location"
Heaven's Hideaway- perfect getaway near the river!

Beautiful Private Cabin, adjacent to the National Forest

9.8 out of 10, Exceptional, (128)
"Peaceful and wonderful. Well appointed and very clean"
Beautiful Private Cabin, adjacent to the National Forest

The Perch Riverfront Cabin - Starlink Wi-Fi

9.4 out of 10, Exceptional, (34)
"A wonderful little A-frame style cabin located right along a bend in the Shenandoah River and just 20 minutes from Luray! It was the perfect little weekend getaway spot to disconnect for a while and enjoy nature. "
The Perch Riverfront Cabin - Starlink Wi-Fi

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

Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

9.2 out of 10, Wonderful, (230)
"Quiet, cozy cabin in serene setting. "
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly: This vacation home rental near Middletown is located on a river and has a fireplace, a balcony, and a barbecue grill 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 a hot tub so you can immerse yourself in your vacation.

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, Cedar Creek Battlefield Foundation and Belle Grove Plantation 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.