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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Property grounds
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (189)
"My family and I stayed with our dog at this beautiful cabin. It was spacious and decorated so nicely. Very cozy and relaxing atmosphere! We will definitely be back."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Mountain Views, River Frontage & HotTub + Country!
Property grounds
Mountain Views, River Frontage & HotTub + Country!
10.0 out of 10, Exceptional, (13)
"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
Property grounds
Star view cabin-Riverfront
9.8 out of 10, Exceptional, (278)
"I have to say the last two reviews made us a bit nervous but those people must have been self-proclaimed critics because we had a truly exceptional experience. Everything was perfect - the hot tub, the river access point, the fire pit(s). A dream come true. We will absolutely be back. Nina’s friendliness and attention to detail made this truly a one of a kind experience. Can’t wait to bring our whole family back!!"
Star view cabin-Riverfront
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Bear Valley- Riverfront with hot tub!
Outdoor dining
Bear Valley- Riverfront with hot tub!
9.8 out of 10, Exceptional, (99)
"A great place to relax, fish, grill-out, & enjoy the hot tub when the sun goes down."
Bear Valley- Riverfront with hot tub!
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
2 bedrooms, WiFi, bed sheets
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
9.8 out of 10, Exceptional, (267)
"My husband, chihuahua and I spent last week in Virginia. The second half was at the Cliffside Cabin. Each morning, we had our coffee sitting on the porch admiring the beautiful mountains and river view. The location was perfect for our outings. We hiked trails, explored Front Royal, saw the Caverns and tubed down the Shenandoah River which was so relaxing! If we're back in the area I would definitely stay here again."
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
Property grounds
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
9.6 out of 10, Exceptional, (151)
"We enjoyed the home but the land even more. Nature is awesome!"
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
Pool
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
10.0 out of 10, Exceptional, (275)
"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!"
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
Falling Leaf Cabin Secluded With Mountain View!
Exterior
Falling Leaf Cabin Secluded With Mountain View!
9.8 out of 10, Exceptional, (259)
"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
Property grounds
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
10.0 out of 10, Exceptional, (334)
"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
2 bedrooms, WiFi, bed sheets
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
9.4 out of 10, Exceptional, (299)
"Loved the cabin. Very cozy. Beautiful views from the deck. Upkeep was great. We really enjoyed the stay and plan to stay again in the future."
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Heaven’s Oasis- Riverfront cabin with hot tub!
Property grounds
Heaven’s Oasis- Riverfront cabin with hot tub!
10.0 out of 10, Exceptional, (6)
"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
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (144)
"Wonderful restful stay in a beautiful cabin with anything you could ever want."
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
Terrace/patio
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
9.2 out of 10, Wonderful, (211)
"It was fun to play parcheesi again!"
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Cozy Lakeside Homestead
Property grounds
Cozy Lakeside Homestead
10.0 out of 10, Exceptional, (166)
"Super close to the lake. Loved kayaking and fishing. Cozy property with everything you need all there. Truly enjoyed our stay."
The price is CA $287
CA $406 total
includes taxes & fees
Jun 9 - Jun 10
Cozy Lakeside Homestead
Captain's Lodge 15 Acres w/300 Meters Of Private Shenandoah Riverfront property
Aerial view
Captain's Lodge 15 Acres w/300 Meters Of Private Shenandoah Riverfront property
9.4 out of 10, Exceptional, (42)
"Although the home was a little dated, we had a wonderful time together with plenty of space. The main room was large enough for everyone to be in w/o being crowded. The host responded quickly to any questions we had. I would recommend it to other large groups if you are not looking for new and modern."
Captain's Lodge 15 Acres w/300 Meters Of Private Shenandoah Riverfront property
Heaven's Hideaway- a perfect getaway on the Shenandoah River!
Property grounds
Heaven's Hideaway- a perfect getaway on the Shenandoah River!
9.8 out of 10, Exceptional, (79)
"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
Property grounds
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
9.8 out of 10, Exceptional, (261)
"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 price is CA $342
CA $514 total
includes taxes & fees
Jun 9 - Jun 10
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Secluded, Cozy Cottage in the Shenandoah Valley
Secluded, Cozy Cottage in the Shenandoah Valley
10.0 out of 10, Exceptional, (145)
"My husband and I stayed for the weekend. While the home is definitely out in the woods, it is not as secluded as we had hoped. There is a large occupied house that looks down on the rental house and hot tub. The ring doorbell can also see the hot tub, and we did not feel like it was private enough for us to use. The house is beautiful and there is plenty of space to wander in the woods."
Secluded, Cozy Cottage in the Shenandoah Valley
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream
Property grounds
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream
10.0 out of 10, Exceptional, (25)
"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!
Property grounds
Family-friendly waterfront cabin with great views & canoes/kayaks. Pets welcome!
9.8 out of 10, Exceptional, (170)
"The views from the property are amazing. The location on the river for fishing and kayaking was convenient. Very responsive owner when issues arose, he brought new grill and coffeemaker during our stay. The house is a 20 minute drive from Luray. While the inside was clean the outside is in need of some TLC, especially the porch screens."
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
Serves dinner and happy hour
Wayside Inn
3.5 star property
9.2 out of 10, Wonderful, (344)
"Nice quiet inn in a historic setting. "
The price is CA $144
CA $158 total
includes taxes & fees
Jun 16 - Jun 17
Wayside Inn
La Quinta Inn & Suites by Wyndham Winchester
Exterior
La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (1372)
"Convenient to I81. Availability of accessible rooms. Continental breakfast."
The price is CA $153
CA $166 total
includes taxes & fees
Jun 10 - Jun 11
La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
Lobby
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (807)
"They are new and clean. Excellent service."
The price is CA $115
CA $125 total
includes taxes & fees
Jun 9 - Jun 10
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.

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middletown vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown vacation rentals we have selected for you start as low as CA $130 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation 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 vacation.

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 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?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This vacation home rental near Middletown is located in the mountains and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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?

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 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.

Recent reviews of Middletown properties
Expedia verified reviews

Comfort Inn & Suites

Comfort Inn & Suites

5/5 Excellent
Just What I Wanted
"We checked in early, 6:30-7:00, and one of their 2 computers was not working yet. Surprisingly, 4 others were also checking in early. Our Accessible room was on the first floor and perfect!"
A verified traveller stayed at Comfort Inn & Suites
Posted 17 hours ago
Comfort Inn & Suites