Photo by Stephanie Sutton

Middletown Holiday 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

In two weeks
In two months
In three months
In four months

Holiday Rentals in Middletown

Our top choices for Middletown holiday rentals

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (381)
"House had all we needed! "
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

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

10.0 out of 10, Exceptional, (324)
"Loved the privacy "
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

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

10.0 out of 10, Exceptional, (335)
"we were looking for a quiet get away, loved having our 16YO boy more interested in fishing and hiking then sitting on his Xbox! We all really loved how quiet and calm it was, definitely plan on going back"
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Falling Leaf Cabin - Rustic Charm With Modern Decor!

9.8 out of 10, Exceptional, (294)
"Great location! It provided the perfect space to unwind. I image the view changes with each season, but always beautiful with a feeling of privacy. "
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (92)
"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, (160)
"A beautiful home and property. This is a wonderful weekend getaway home. Modern and comfortable, but especially quiet!"
Secluded River Cabin Getaway (Masten Cabin)

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

9.6 out of 10, Exceptional, (60)
"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 AU$499
includes taxes & fees
8 Sept - 9 Sept
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (326)
"My family loves Shenandoah NP and we’ve stayed at multiple places. This cabin was perfect for us! The views were amazing!"
Star view cabin-Riverfront

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

9.8 out of 10, Exceptional, (192)
"The cabin is an absolute gem, located in the mountains but within easy reach of groceries, restaurants, hiking, fishing, etc. The stay was spacious, clean, tidy, had plenty of entertainment options, and communication was timely. Would not hesitate to book again. "
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

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

9.6 out of 10, Exceptional, (190)
"We had a great time sitting on the porch relaxing. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

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

9.2 out of 10, Wonderful, (235)
"Nice cabin to relax and unwind. "
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

Luxury Cabin Getaway in the Blue Ridge Mountains

Luxury Cabin Getaway in the Blue Ridge Mountains

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

10.0 out of 10, Exceptional, (10)
"2 night stay celebrating our 21 year anniversary! Host was attentive & communicated through text daily to check how our stay was going! Unique property grounds & highly enjoyable!"
The price is AU$443
includes taxes & fees
3 Sept - 4 Sept
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

9.4 out of 10, Exceptional, (142)
"Myself and a few friends stayed here in late April. The views from the cabin are as good or better than many on the Appalachian Trail or other nearby trails and parks, and the cabin itself was well appointed. The hosts were great and very prompt with communication. The road and driveway to access the property are gravel and somewhat steep, but I didn't feel like we needed high clearance or 4 wheel drive at any point (in good weather). I would definitely stay here again."
Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

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

10.0 out of 10, Exceptional, (46)
"We had a nice stay at this location. The property managers were extremely quick to respond and helpful pointing out must visit locations while at the property."
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

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

10.0 out of 10, Exceptional, (34)
"Very nice location, would stay here again. Had everything we needed."
Cabin near River, Firepit, Family-friendly, WiFi, Great Location, Veteran owned!

Cozy Retreat - Hot tub + Mountain Views + Pets

9.8 out of 10, Exceptional, (48)
"An amazing stay disconnected from life and close to hiking, sightseeing, and popular attractions. We cooked and read and napped. I would love to come here again!"
The price is AU$388
includes taxes & fees
9 Sept - 10 Sept
Cozy Retreat - Hot tub + Mountain Views + Pets

Apple Mountain Retreat

10.0 out of 10, Exceptional, (15)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is AU$365
includes taxes & fees
27 Aug - 28 Aug
Apple Mountain Retreat

Mountain View Bungalow in Front Royal

"Excelente propiedad "
The price is AU$377
includes taxes & fees
27 Aug - 28 Aug
Mountain View Bungalow in Front Royal

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

9.8 out of 10, Exceptional, (61)
"Great location beautiful place"
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi
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

Top Middletown Hotel Reviews

Find out more about Middletown

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as AU$365 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub: 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. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your 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, Cedar Creek Battlefield Foundation and Belle Grove Plantation 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.