Middletown Vacation Rentals

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Our top choices for Middletown vacation rentals

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.4 out of 10, Exceptional, (13 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (25 reviews)
"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"
United States
Brian B.
The price is CA $185
CA $301 total
includes taxes & fees
May 14 - May 15
Mountain View Bungalow in Front Royal

Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (28 reviews)
"Great place. Very clean, lots of comfortable rooms. Nice outside area for dogs. "
United States
Lisa W.
The price is CA $274
CA $627 total
includes taxes & fees
May 17 - May 18
Hidden Gem on Hidden Valley Lane

River Access Cabin w Hot Tub, Deck, Grill, & Wifi

River Access Cabin w Hot Tub, Deck, Grill, & Wifi
Luray
8.6 out of 10, Excellent, (27 reviews)
"As it is described. Clean and peaceful. "
United States
Anna A.
The price is CA $243
CA $460 total
includes taxes & fees
Jun 2 - Jun 3
River Access Cabin w Hot Tub, Deck, Grill, & Wifi

Modern Riverside Cabin w Hot Tub, Fire Pit, Kayaks

Modern Riverside Cabin w Hot Tub, Fire Pit, Kayaks
Rileyville
9.6 out of 10, Exceptional, (4 reviews)
"We had an absolute wonderful time! It was so relaxing and the descriptions were spot on. After reading the reviews, we brought our foam mattress cover for the bed and it made a big difference. The public fishing spot near the cabin is also a boat launch spot so we had some traffic while fishing but we still caught some fish! Rivers Edge is also on the corner lot so we felt it was very private and highly recommend! The hot tub was also a perfect touch. 10/10 vacation! Thanks Tony! "
United States
Allison S.
The price is CA $277
CA $432 total
includes taxes & fees
May 14 - May 15
Modern Riverside Cabin w Hot Tub, Fire Pit, Kayaks

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (34 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Host was responsive and helpful. Would definitely stay again."
United States
Wafaa L.
The price is CA $260
CA $324 total
includes taxes & fees
May 14 - May 15
Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain House - Hot Tub, Grill, Fire Table

Blue Mountain House - Hot Tub, Grill, Fire Table
Linden
The price is CA $212
CA $696 total
includes taxes & fees
May 26 - May 27
Blue Mountain House - Hot Tub, Grill, Fire Table

Skyland Hideaway | Mountain Cabin w/ Hot Tub

Skyland Hideaway | Mountain Cabin w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (15 reviews)
"Quiet with amenities to support R&R, enjoying nature, and togetherness."
United States
Patricia B.
The price is CA $212
CA $575 total
includes taxes & fees
May 14 - May 15
Skyland Hideaway | Mountain Cabin w/ Hot Tub

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (23 reviews)
"Great place to stayed "
United States
Mike F.
The price is CA $185
CA $314 total
includes taxes & fees
May 25 - May 26
Apple Mountain Retreat

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

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Rileyville
10.0 out of 10, Exceptional, (361 reviews)
"It was exactly what we needed, out of the way and in nature, but close to beautiful attractions and grocery stores "
United States
Aaron A.
The price is CA $208
CA $372 total
includes taxes & fees
May 14 - May 15
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub

"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub
Rileyville
10.0 out of 10, Exceptional, (327 reviews)
"Incredible views!!"
United States
anthony c.
The price is CA $204
CA $368 total
includes taxes & fees
May 20 - May 21
"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (22 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
The price is CA $185
CA $524 total
includes taxes & fees
May 18 - May 19
The Juniper Cabin • Cozy Hideaway w/ Hot Tub

Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (4 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
The price is CA $198
CA $246 total
includes taxes & fees
Jun 1 - Jun 2
Luxury tiny home farm stay on historic property with hot tub in Stephens City

Apple Mountain House • Hot Tub • Game Room

Apple Mountain House • Hot Tub • Game Room
Front Royal
9.8 out of 10, Exceptional, (12 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is CA $242
CA $579 total
includes taxes & fees
May 17 - May 18
Apple Mountain House • Hot Tub • Game Room

Cozy cabin w/hot tub & fire pit

Cozy cabin w/hot tub & fire pit
Rio
9.4 out of 10, Exceptional, (6 reviews)
"Enjoyed our stay very much!! Enjoyed the hot tub and the space very much. "
United States
Melissa M.
The price is CA $221
CA $474 total
includes taxes & fees
May 27 - May 28
Cozy cabin w/hot tub & fire pit

Private Cabin in the woods w/ firepit right next to Shenandoah River

Private Cabin in the woods w/ firepit right next to Shenandoah River
Bentonville
10.0 out of 10, Exceptional, (35 reviews)
"Awesome spot…clean, cozy, private. Hosts were very responsive- can’t ask for anything more "
United States
Asim K.
The price is CA $204
CA $462 total
includes taxes & fees
May 19 - May 20
Private Cabin in the woods w/ firepit right next to Shenandoah River

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

Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Luray
9.6 out of 10, Exceptional, (76 reviews)
"Very nice place and very well set up and welcoming."
United States
Adam Y.
The price is CA $180
CA $427 total
includes taxes & fees
May 27 - May 28
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Lookout Cabin in the mountains, Amazing Views!

Lookout Cabin in the mountains, Amazing Views!
Page County
9.8 out of 10, Exceptional, (38 reviews)
"Nice cabin for Holliday getaway. great views"
United States
Raymond F.
Lookout Cabin in the mountains, Amazing Views!

The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.8 out of 10, Good, (7 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is CA $129
CA $287 total
includes taxes & fees
May 19 - May 20
The Queen of Winchester Three Bedroom with Upper Level Deck
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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Top Middletown Hotel Reviews

Find out more about Middletown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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. 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. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your 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 lovely local spots to get outside and enjoy nature. 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.