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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, 191 reviews
"Overall we enjoyed our stay. A couple things of note: Bringing black out shades is super helpful! The closet in the bedroom is big enough for a portable crib. Be sure to bring toilet paper. We only had one full and one partial roll between the two bathrooms(and they were paper thin). Because there isn’t anywhere super close, it’s nice to know to pack some ahead of time :) The road is so peaceful and we went on the trail quite a few times. It was a bit wet, so we didn’t make it all the way...
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Mountain Views, River Frontage & HotTub + Country!
10.0 out of 10, Exceptional, 13 reviews
"Took my kids 13 11 and 7 they had a great time at river and cooking out and s'mores over the fire and hot tub was a plus"
Mountain Views, River Frontage & HotTub + Country!
Star view cabin-Riverfront
9.8 out of 10, Exceptional, 280 reviews
"My husband and I really enjoyed our long weekend! The first night's sunset was spectacular and we really enjoyed relaxing by the river. The cabin was spacious and the beds comfortable. Our only issue was the condition of some of the cookware and kitchen items. Otherwise, we highly recommend this property."
Star view cabin-Riverfront
Bear Valley- Riverfront with hot tub!
9.8 out of 10, Exceptional, 101 reviews
"We had a great time spending a long holiday weekend here. It was relaxing and peaceful and perfect for what we needed. However I would say the place needs some work and the owner should put some money back into it. The directv barely works and the internet is non existent but we made due without it. Cosmetically it needs some love. If it got some love we’d probably visit frequently however next time we’ll probably look for a more put together place. Location is fantastic so if you’re cool with...
Bear Valley- Riverfront with hot tub!
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
9.8 out of 10, Exceptional, 269 reviews
"Great views, lots of wildlife, peaceful, the mountain goat trail to the water was interesting."
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
9.6 out of 10, Exceptional, 153 reviews
"Wonderful, comfy , gorgeous, restful"
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
10.0 out of 10, Exceptional, 276 reviews
"Our stay at Solitude was absolutely wonderful! The property was exactly as described, clean and beautiful. My wife and I loved our weekend away. We enjoyed sitting in the hot tub, relaxing by the campfire and watching nature go by. It was exactly what we needed for our anniversary, a place away from the business of our everyday lives. Highly recommend this place to anyone who is looking to get away!"
The price is NZ$528
includes taxes & fees
22 July - 23 July
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
Falling Leaf Cabin Secluded With Mountain View!
9.8 out of 10, Exceptional, 259 reviews
"This cabin was perfect for a peaceful getaway. It was clean and well taken care of. The porch was my favorite part of the house! What a great way to get away from busy northern Virginia!"
Falling Leaf Cabin Secluded With Mountain View!
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
10.0 out of 10, Exceptional, 334 reviews
"We enjoyed our stay"
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
9.4 out of 10, Exceptional, 301 reviews
"We loved the cabin. Furniture and pots & pans could use a serious update. I cook all the time but it was very difficult with the old pots & pans."
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Heaven’s Oasis- Riverfront cabin with hot tub!
10.0 out of 10, Exceptional, 6 reviews
"Property was great when we were there, the only thing that was a bummer was I think the pool pump was back flushing in the middle of the night. I think it was on a timer At 2:30 am and ran for a long time and we had to shut the windows because of the noise of running water. Also most mornings at 6:00 the pool was being filled on a timer and the pump ran for at least 4 hours at a time, so there was not much water pressure so couldn’t take a morning shower. Most windows did not have screen and the...
Heaven’s Oasis- Riverfront cabin with hot tub!
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, 147 reviews
"We arrived Thursday afternoon and stayed until Sunday morning. It was the most peaceful time away I have ever had. Everyone had a wonderful time and thought the house was amazing. Completely loved my time on Half Moon Lane!"
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
9.2 out of 10, Wonderful, 211 reviews
"It was fun to play parcheesi again!"
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Cozy Lakeside Homestead
10.0 out of 10, Exceptional, 168 reviews
"We had a wonderful weekend at you sweet beautiful cottage. Thank you for the delicious cookies and wine what a special treat. We saw lots of deer. We had fun walking around the lake. Thank you for sharing your rental."
The price is NZ$486
includes taxes & fees
11 July - 12 July
Cozy Lakeside Homestead
Captain's Lodge 15 Acres w/300 Meters Of Private Shenandoah Riverfront property
9.4 out of 10, Exceptional, 43 reviews
"This was honestly everything we hoped it would be! Beautiful landscape, river access, plenty of space at the Captains Lodge to relax and enjoy yourself or play games with the family. We enjoyed the entire stay! Internet was not great, but also we were fine with unplugging and just enjoying the nature. Would recommend to anyone who enjoys playing in the river and having BBQ and campfires with the comfort of an amazing house to rest your head (:"
Captain's Lodge 15 Acres w/300 Meters Of Private Shenandoah Riverfront property
Heaven's Hideaway- a perfect getaway on the Shenandoah River!
9.8 out of 10, Exceptional, 79 reviews
"This is a well-kept, clean and quite getaway location. It was perfect for a couple's quick escape from the daily grind. It was perfect for the two of us and presented a very welcoming and comfortable living environment. It has a great balance that makes you feel comfortable using the amenities and simply feeling at home. Relaxing and watching a sunrise/sunset from the hot tub is simply icing on the cake. April was perhaps an idea time to visit as the foliage was not fully out it provided a...
Heaven's Hideaway- a perfect getaway on the Shenandoah River!
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
9.8 out of 10, Exceptional, 261 reviews
"We stayed for a total of 4 nights. Our first reaction when we pulled in was that the road was a gravel road and on a very steep hill, which is definitely not stated on the listing. The outside and inside of the cabin is nice and I would say clean. The only reason I would give this cabin such a low rating was because of the amenities… and the wasp nest on the deck. We were trying to enjoy the hot tub outside and had to cut it short because a carpenter bee was digging itself a home inside the...
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Secluded, Cozy Cottage in the Shenandoah Valley
10.0 out of 10, Exceptional, 146 reviews
"Very peaceful, clean, up to date and great location. Hiked to the top of the mountain on a well maintained several mile trail on the property with incredible views. Thank you to the hosts and will plan to visit again. What a great tranquil place to relax!"
Secluded, Cozy Cottage in the Shenandoah Valley
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream
10.0 out of 10, Exceptional, 25 reviews
"The pictures and description are 100% accurate, but being there in person to take in the peaceful surroundings and views of nature with the family was a great experience. The hostess was responsive from the moment we booked and provided all the info we needed to make it to this mountain top cabin on the VA/WV border. We drove up on a Friday and after getting out of DC traffic we were on our way to Almost Heaven cabin. When we’re about a mile or so from the cabin we saw a black bear crossing...
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream
Family-friendly waterfront cabin with great views & canoes/kayaks. Pets welcome!
9.8 out of 10, Exceptional, 171 reviews
"Our 5-day stay on the banks of the river celebrated a family milestone in comfort and beauty. The cottage was spacious with multiple dining areas (2) and gathering areas (4) both inside and outside. All the appliances served us well, and the beds were comfortable. We appreciated the quiet neighbors and no outboard motors on the river. Having kayaks and canoes on the property (no need to rent) was a real highlight. Two unfavorable aspects: the cottage could have used a beginning-of-the-season...
Family-friendly waterfront cabin with great views & canoes/kayaks. Pets welcome!
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See all available properties in Middletown
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.

Other types of properties in Middletown you may be interested in

Wayside Inn
3.5 star property
9.2 out of 10, Wonderful, 346 reviews
"Nice quiet inn in a historic setting. "
The price is NZ$189
includes taxes & fees
25 June - 26 June
Wayside Inn
La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, 1,397 reviews
"I believe this was the first time we have ever stayed at La Quinta and we will definitely return. I hope all are like this one in Winchester. The place was so very clean in the breakfast area in the hallways on the elevators in the bedrooms. Generally have one fruit for breakfast if you're lucky but they had five including grapefruit which I have never seen. The bed was extremely comfortable and I liked the ability to close off the toilet shower from the sink area. All the amenities with the...
The price is NZ$190
includes taxes & fees
30 June - 1 July
La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, 826 reviews
"Everything"
The price is NZ$155
includes taxes & fees
1 July - 2 July
Microtel Inn & Suites by Wyndham Winchester
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middletown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middletown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Middletown. Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Middletown short-term rentals, that won’t be hard to do.

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?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This holiday home rental outside of Middletown is located in a rural location, 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. You can relax into your holiday with a garden and a selection of games.

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?

Shenandoah River and Cedar Creek and Belle Grove National Historical Park 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.

Recent reviews of Middletown properties
Expedia verified reviews