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Middletown Vacation Rentals

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Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 24 - Oct 26
In two weeks
Oct 31 - Nov 2

Vacation Rentals in Middletown

Interior
Pretty Little Apt by the Train II
Pretty Little Apt by the Train II
2.0 star property
10.0 out of 10, Exceptional, (4)
"Great time. Love this city"
United States
Barbara B.
$192 nightly
The price is $218
Oct 19 - Oct 20
Total with taxes and fees
Pretty Little Apt by the Train II
Smart TV, stereo
Cozy Retreat - Hot tub + Mountain Views + Pets
Cozy Retreat - Hot tub + Mountain Views + Pets
9.8 out of 10, Exceptional, (51)
"This house was super charming and perfect for our weekend getaway!"
United States
Beth S.
$224 nightly
The price is $247
Oct 19 - Oct 20
Total with taxes and fees
Cozy Retreat - Hot tub + Mountain Views + Pets
Terrace/patio
Large Glamper w/ Hot Tub and full bathroom-sleep 6
Large Glamper w/ Hot Tub and full bathroom-sleep 6
10.0 out of 10, Exceptional, (23)
"We absolutely loved this place! The glamper had everything we needed and more! The hot tub was super relaxing and the host is super responsive! Would definitely stay here again in the future."
United States
Anonymous traveler
$160 nightly
The price is $179
Oct 20 - Oct 21
Total with taxes and fees
Large Glamper w/ Hot Tub and full bathroom-sleep 6
Fridge, microwave, oven, stovetop
Mountain View Bungalow in Front Royal
Mountain View Bungalow in Front Royal
10.0 out of 10, Exceptional, (4)
"Property was just what we were looking for "
United States
Tim C.
$198 nightly
The price is $220
Oct 20 - Oct 21
Total with taxes and fees
Mountain View Bungalow in Front Royal
Terrace/patio
Luxury Riverfront Home Getaway with Hot Tub
Luxury Riverfront Home Getaway with Hot Tub
2.0 star property
$445 nightly
The price is $461
Nov 4 - Nov 5
Total with taxes and fees
Luxury Riverfront Home Getaway with Hot Tub
Outdoor spa tub
Fox Den — Hot Tub, Fire Pit, Steps to River
Fox Den — Hot Tub, Fire Pit, Steps to River
10.0 out of 10, Exceptional, (6)
"We loved the house it was just what we wanted and needed. The place was very clean and spacious we took 2 small dogs with us and it was perfect for them. Very close to what we wanted to do but still peaceful. "
United States
Leslie
$321 nightly
The price is $347
Oct 20 - Oct 21
Total with taxes and fees
Fox Den — Hot Tub, Fire Pit, Steps to River
Private kitchen
Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
2.0 star property
$229 nightly
The price is $259
Oct 19 - Oct 20
Total with taxes and fees
Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Outdoor spa tub
Charming 3-bedroom cabin with Moutain Views, Hottub, WiFi in Shenandoah.
Charming 3-bedroom cabin with Moutain Views, Hottub, WiFi in Shenandoah.
2.0 star property
10.0 out of 10, Exceptional, (26)
"We loved our stay. The home comfortably accomodated our party of 4 with pups at the last-minute. We really appreciated the kind and well-thought special touches!"
United States
Kara P.
$280 nightly
The price is $323
Nov 4 - Nov 5
Total with taxes and fees
Charming 3-bedroom cabin with Moutain Views, Hottub, WiFi in Shenandoah.
Fridge, microwave, oven, stovetop
Peaceful Retreat on Creekside
Peaceful Retreat on Creekside
9.4 out of 10, Exceptional, (10)
"We liked being out in the country. Loved hearing the sounds of the woods and the farms. Lovely spot"
United States
Amanda
$195 nightly
The price is $215
Oct 20 - Oct 21
Total with taxes and fees
Peaceful Retreat on Creekside
Terrace/patio
Cute cabin retreat near Shenandoah National Park and pet friendly!
Cute cabin retreat near Shenandoah National Park and pet friendly!
9.4 out of 10, Exceptional, (12)
"Very relaxing end to out Appalachian Trail hike. The hot tub was so relaxing. It was the perfect way to end a strenuous day."
United States
Jean L.
$356 nightly
The price is $393
Nov 6 - Nov 7
Total with taxes and fees
Cute cabin retreat near Shenandoah National Park and pet friendly!
Exterior
Whitetail Cabin | Couple`s Retreat w/ Hot Tub
Whitetail Cabin | Couple`s Retreat w/ Hot Tub
10.0 out of 10, Exceptional, (21)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
$332 nightly
The price is $366
Nov 16 - Nov 17
Total with taxes and fees
Whitetail Cabin | Couple`s Retreat w/ Hot Tub
Terrace/patio
Remote Riverfront Cabin: Hot Tub * Fast Wi-Fi * Disc Golf * Pool Table * Games!
Remote Riverfront Cabin: Hot Tub * Fast Wi-Fi * Disc Golf * Pool Table * Games!
10.0 out of 10, Exceptional, (14)
"The place was awesome"
United States
Robert
$379 nightly
The price is $437
Oct 19 - Oct 20
Total with taxes and fees
Remote Riverfront Cabin: Hot Tub * Fast Wi-Fi * Disc Golf * Pool Table * Games!
Exterior
Cozy English Basement Apt quiet but close to downtown
Cozy English Basement Apt quiet but close to downtown
9.6 out of 10, Exceptional, (7)
"Downtown Winchester is charming, and the property was an easy walk from downtown (though in a safe suburban neighborhood). The property itself was just as advertised. I was able to cook meals there; the bed was comfortable; it was much nicer and more varied than a hotel room."
United States
Sherwood W.
$155 nightly
The price is $176
Oct 20 - Oct 21
Total with taxes and fees
Cozy English Basement Apt quiet but close to downtown
TV, fireplace, offices
Skyland Hideaway | Mountain Cabin w/ Hot Tub
Skyland Hideaway | Mountain Cabin w/ Hot Tub
10.0 out of 10, Exceptional, (14)
"We just stayed at SkyLand The house was clean, comfortable and welcoming. Matt is a great host Very responsive. The hot tub needed more water...no big deal. The beds were comfy and the coffee much appreciated upon arrival. Definitely wanna stay again."
United States
Virginia
$384 nightly
The price is $424
Nov 2 - Nov 3
Total with taxes and fees
Skyland Hideaway | Mountain Cabin w/ Hot Tub
Outdoor spa tub
Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets
Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets
2.0 star property
$297 nightly
The price is $327
Oct 21 - Oct 22
Total with taxes and fees
Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets
Terrace/patio
Cozy Fall Cabin on 17 acres by National Park, EV Charger
Cozy Fall Cabin on 17 acres by National Park, EV Charger
2.0 star property
10.0 out of 10, Exceptional, (5)
"This home was very secluded and had beautiful views. The interior was a perfect mix of historic and modern touches. Hosts were very responsive and we would stay here again!"
United States
Cyndi B.
$337 nightly
The price is $372
Oct 19 - Oct 20
Total with taxes and fees
Cozy Fall Cabin on 17 acres by National Park, EV Charger
Terrace/patio
The Zen Garden by Zen Living
The Zen Garden by Zen Living
9.6 out of 10, Exceptional, (15)
"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.
$278 nightly
The price is $320
Oct 21 - Oct 22
Total with taxes and fees
The Zen Garden by Zen Living
Terrace/patio
Cabin Retreat in Virginia Wine Country – Hot Tub, Theater Room & Pet-Friendly
Cabin Retreat in Virginia Wine Country – Hot Tub, Theater Room & Pet-Friendly
9.8 out of 10, Exceptional, (10)
"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.
$386 nightly
The price is $426
Nov 4 - Nov 5
Total with taxes and fees
Cabin Retreat in Virginia Wine Country – Hot Tub, Theater Room & Pet-Friendly
Property grounds
Reel It In Cabin
Reel It In Cabin
9.6 out of 10, Exceptional, (47)
"This is a beautiful property nearby the Shenandoah River. Quiet, clean, well-furnished, cozy, great hot-tube. Perfect for those who need to rest and spend a relaxing time."
United States
Saulo V.
$276 nightly
The price is $308
Oct 20 - Oct 21
Total with taxes and fees
Reel It In Cabin
Exterior
Wilderness Ridge | Private Cabin w/ Mountain Views
Wilderness Ridge | Private Cabin w/ Mountain Views
9.6 out of 10, Exceptional, (4)
"great get away for a family retreat!!!"
United States
Rex P.
$479 nightly
The price is $528
Nov 2 - Nov 3
Total with taxes and fees
Wilderness Ridge | Private Cabin w/ Mountain Views
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

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 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?

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. Kitchen amenities include a dishwasher, a fridge, and a stovetop. 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 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 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.