Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Middletown vacation rentals

Outdoor spa 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.
$349 nightly
The price is $385
Jun 30 - Jul 1
Total with taxes and fees
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Property grounds

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

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Rileyville
9.8 out of 10, Exceptional, (327 reviews)
"Cabin had rustic vibes but is very well taken care of and clean."
United States
Heidi
$241 nightly
The price is $278
Jun 25 - Jun 26
Total with taxes and fees
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Exterior

Mountain Retreat w/ Loft, Fire Pit, & Grill

Mountain Retreat w/ Loft, Fire Pit, & Grill
Delray
9.0 out of 10, Wonderful, (10 reviews)
"The cabin was nice and clean and had everything we needed for a 2 night stay."
United States
Karen
$203 nightly
The price is $224
Jun 25 - Jun 26
Total with taxes and fees
Mountain Retreat w/ Loft, Fire Pit, & Grill
Property grounds

Peaceful Retreat on Creekside

Peaceful Retreat on Creekside
Edinburg
9.2 out of 10, Wonderful, (17 reviews)
"Amazing location that was perfect for a weekend getaway! The creek was so peaceful and water views from the deck were amazing! "
United States
Richard D.
$202 nightly
The price is $222
Jun 29 - Jun 30
Total with taxes and fees
Peaceful Retreat on Creekside
TV, fireplace, foosball, offices

Delicious Cabin • Wine Country Retreat w/ Hot Tub

Delicious Cabin • Wine Country Retreat w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (11 reviews)
"The cabin was impressive both inside and out. We loved the location and proximity to skyline drive. We would definitely stay here again as it made our trip so much more enjoyable. "
United States
Bill A.
$413 nightly
The price is $456
Jun 28 - Jun 29
Total with taxes and fees
Delicious Cabin • Wine Country Retreat w/ Hot Tub
Terrace/patio

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, (6 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
$165 nightly
The price is $184
Jul 12 - Jul 13
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Interior

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, (79 reviews)
"Very nice place and very well set up and welcoming."
United States
Adam Y.
$291 nightly
The price is $333
Jun 28 - Jun 29
Total with taxes and fees
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (27 reviews)
"We had a great stay! The house is cozy and just perfect for a private get away. The hosts were very communicative and wonderful, we will be back! "
United States
Virginia A.
$198 nightly
The price is $220
Jun 25 - Jun 26
Total with taxes and fees
Mountain View Bungalow in Front Royal
Property grounds

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, (36 reviews)
"Awesome spot…clean, cozy, private. Hosts were very responsive- can’t ask for anything more "
United States
Asim K.
$304 nightly
The price is $335
Jun 25 - Jun 26
Total with taxes and fees
Private Cabin in the woods w/ firepit right next to Shenandoah River
Outdoor spa tub

Stargaze from Hot Tub Pet-Friendly Mtn Cabin

Stargaze from Hot Tub Pet-Friendly Mtn Cabin
Page County
9.6 out of 10, Exceptional, (15 reviews)
"King size bed, fenced yard for our dog, and good mid-week price are what made us choose this place for a short get away. It really suited our needs and we'll be back! Bed was comfortable. House was clean, nicely decorated, and felt welcoming. Could not get WiFi to work, but our cell phone reception was fine."
United States
Joyce F.
$263 nightly
The price is $303
Jun 29 - Jun 30
Total with taxes and fees
Stargaze from Hot Tub Pet-Friendly Mtn Cabin
Exterior

Blue Mountain House - Hot Tub, Grill, Fire Table

Blue Mountain House - Hot Tub, Grill, Fire Table
Linden
$412 nightly
The price is $454
Jul 12 - Jul 13
Total with taxes and fees
Blue Mountain House - Hot Tub, Grill, Fire Table
TV

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
$205 nightly
The price is $226
Jun 30 - Jul 1
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Pool

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

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Rileyville
10.0 out of 10, Exceptional, (363 reviews)
"Fantastic stay! Will definitely come back!"
United States
Tristan T.
$241 nightly
The price is $278
Jun 25 - Jun 26
Total with taxes and fees
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
TV, fireplace

Mountain retreat chalet w/ hot tub & deck

Mountain retreat chalet w/ hot tub & deck
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.
$290 nightly
The price is $313
Jun 30 - Jul 1
Total with taxes and fees
Mountain retreat chalet w/ hot tub & deck
Terrace/patio

Lake-view! Hot Tub! Fire Pit. Grill. Game Room. King bed.

Lake-view! Hot Tub! Fire Pit. Grill. Game Room. King bed.
Luray
9.6 out of 10, Exceptional, (40 reviews)
"the host came mid stay to refill the hot tub! wasn’t expecting that at all. super attentive and kind hosts - beautiful stay! "
United States
Miranda B.
$380 nightly
The price is $438
Jul 20 - Jul 21
Total with taxes and fees
Lake-view! Hot Tub! Fire Pit. Grill. Game Room. King bed.
Property grounds

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, (36 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.
$215 nightly
The price is $237
Jun 25 - Jun 26
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
Terrace/patio

Reel It In Cabin

Reel It In Cabin
Page County
9.6 out of 10, Exceptional, (51 reviews)
"The Reel It Inn Cabin is clean and cozy, stocked with everything you need for a nice get-away. The hot tub was lovely especially on the clear crisp nights we had for our stay. Stargazing while hot tubbing? Yes please! The hosts made sure to communicate anything we needed to know for our stay and even let us know how to reach them once we were at the cabin. 10/10 will stay here again! "
United States
Kait V.
$345 nightly
The price is $378
Jun 25 - Jun 26
Total with taxes and fees
Reel It In Cabin
Smart TV, fireplace, DVD player, books

Cozy Log Cabin w Porch, Fire Pit, Games & River

Cozy Log Cabin w Porch, Fire Pit, Games & River
Maurertown
9.6 out of 10, Exceptional, (42 reviews)
"Wonderful cabin, had a great time! "
United States
Katherine R.
$419 nightly
The price is $467
Jun 25 - Jun 26
Total with taxes and fees
Cozy Log Cabin w Porch, Fire Pit, Games & River
Outdoor spa tub

Cast Away Cabin

Cast Away Cabin
Page County
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful and relaxing stay. Nice peaceful location. Would definitely stay here again!"
United States
Jeremy H.
$363 nightly
The price is $399
Jun 25 - Jun 26
Total with taxes and fees
Cast Away Cabin
Exterior

Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
10.0 out of 10, Exceptional, (6 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
$236 nightly
The price is $260
Jul 21 - Jul 22
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Staff and hotel were top notch i will stay here again and again!"
Steven 1-night trip
Posted 2 hours ago
Quality Inn Winchester

Find out more about Middletown

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $220 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Secluded River Cabin Getaway (Masten Cabin): This vacation home rental near Middletown is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in Middletown?

Shenandoah River and Cedar Creek and Belle Grove National Historical Park are a couple of lovely local spots to get outside and enjoy nature. While here, Belle Grove Plantation and Jackson's Chase Golf Course 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.