Photo by Stephanie Sutton

Middletown Vacation Rentals

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Vacation Rentals in Middletown

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (312)
"very cute little place, would definitely stay again"
Star view cabin-Riverfront

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (83)
"The cabin is beautiful and tucked away in the trees. Amazing colors this time of year and was such a great little getaway. Highly recommend staying here!"
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Falling Leaf Cabin With Winter River And Mountain View!

9.8 out of 10, Exceptional, (282)
"Fourth time here and it never gets old!!! absolutely gorgeous!"
Falling Leaf Cabin With Winter River And Mountain View!

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

9.6 out of 10, Exceptional, (309)
"The cabin is a very cozy getaway location, with a great view just out the window."
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

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

9.8 out of 10, Exceptional, (284)
"The Chalet was perfect for our quick trip in Luray! Very clean and absolutely beautiful views. Thank you! "
The price is CA $235
CA $400 total
includes taxes & fees
May 1 - May 2
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

Bear Valley- Riverfront with hot tub!

9.6 out of 10, Exceptional, (116)
"Beautiful place, perfect for a quiet family getaway! Property manager was super responsive. Will love to stay again. "
Bear Valley- Riverfront with hot tub!

The Perch Riverfront Cabin - Starlink Satellite Wi-Fi

9.4 out of 10, Exceptional, (31)
"Perfect cabin in the ideal setting"
The Perch Riverfront Cabin - Starlink Satellite Wi-Fi

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (40)
"Had a wonderful stay - - beautiful country and delightful cottage."
Historical cottage in the town of Paris

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.6 out of 10, Exceptional, (349)
"This cabin stay was wonderful. It is perched high on a cliff and the views are spectacular. The cabin is secluded which makes for a nice relaxing stay. I can't wait to come back."
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

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

10.0 out of 10, Exceptional, (309)
"We had a wonderful and recuperative weekend at Solitude. We especially enjoyed the hot tub and the fireplace. Perfect!"
The price is CA $242
CA $405 total
includes taxes & fees
May 11 - May 12
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Magical Riverfront Retreat in Luray – Cozy Getaway with Stunning Views!

9.8 out of 10, Exceptional, (179)
"Wonderful property I hope to be back during warmer weather"
Magical Riverfront Retreat in Luray – Cozy Getaway with Stunning Views!

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (171)
"We enjoyed our stay at this lovely property."
Secluded, Cozy Cottage in the Shenandoah Valley

Heaven's Hideaway- a perfect getaway near the Shenandoah River!

9.6 out of 10, Exceptional, (104)
"Cabin was very cozy and comfortable for two people. "
Heaven's Hideaway- a perfect getaway near the Shenandoah River!

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

9.6 out of 10, Exceptional, (174)
"Beautiful location and property. The house is rustic and had trouble getting the heat to work. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Cozy Lakeside Homestead

10.0 out of 10, Exceptional, (190)
"Had a great time with my wife and dog. 5/5 across the board!"
The price is CA $290
CA $405 total
includes taxes & fees
May 26 - May 27
Cozy Lakeside Homestead

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

9.6 out of 10, Exceptional, (56)
"Wonderful property and greats views "
The price is CA $202
CA $459 total
includes taxes & fees
May 1 - May 2
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!

10.0 out of 10, Exceptional, (44)
"We have rented Shiloh Lodge several times for fishing and hunting. The guys love this lodge. Convenient to the river and hunting across the road."
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!

Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

9.4 out of 10, Exceptional, (133)
"We decided to stay up here to enjoy a couple friends birthdays, and it was the perfect stay. Great location with plenty of things to do a short drive away. Would stay here again!"
Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

Cozy Retreat - Hot tub + Mountain Views + Pets

10.0 out of 10, Exceptional, (26)
"Great time at a great place"
The price is CA $132
CA $373 total
includes taxes & fees
May 20 - May 21
Cozy Retreat - Hot tub + Mountain Views + Pets

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

10.0 out of 10, Exceptional, (38)
"Great and communicative host. Very accommodating. Spent a few hours in the hot tub enjoying the stars. Great kitchen to cook a lovely meal. Would stay again!"
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
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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Other types of properties in Middletown you may be interested in

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (387)
"This inn is absolutely amazing. Staff went above and beyond to ensure we were comfortable and our stay was memorable. We plan to come back very soon! "
The price is CA $145
CA $174 total
includes taxes & fees
May 1 - May 2
Wayside Inn

La Quinta Inn & Suites by Wyndham Winchester

3.0 star property
9.2 out of 10, Wonderful, (1969)
"Very nice hotel, friendly staff, great breakfast "
The price is CA $129
CA $141 total
includes taxes & fees
May 4 - May 5
La Quinta Inn & Suites by Wyndham Winchester

Comfort Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (1008)
"Great stay. Would definitely stay here again."
The price is CA $140
CA $152 total
includes taxes & fees
May 4 - May 5
Comfort Inn & Suites
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.

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?

Cozy Lakeside Homestead: This vacation home near Middletown is located on a lake and has a fireplace, a patio, 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.

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.