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Compare 148 Vacation Homes in Middletown with updated reviews, rates, and availability.

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (197)
"Our host was very accommodating. We had a lovely time and hope to return "
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
10.0 out of 10, Exceptional, (347)
"Great spot for our girls getaway! Very remote with fantastic views. Front deck was wonderful for morning coffee and sunset watching! Definitely requires a truck or SUV for the road up. Lots of extra towels and plenty of space for all! Great spot! "
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
9.6 out of 10, Exceptional, (162)
"Had another wonderful stay at the farmhouse. You can't beat the scenery, sunsets over the Shenandoah River with the mountains in the backdrop. You can canoe, fish, swim, hike right on the property. Lots beautiful trees and wildlife. Thank you Nina for being a great host and sharing this with our family!"
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
Secluded River Cabin Getaway (Masten Cabin)
9.8 out of 10, Exceptional, (132)
"Nice property sitting on hill. All items in home as advertised. Great screened 2nd level porch. We enjoyed a pleasant weekend!"
Secluded River Cabin Getaway (Masten Cabin)
Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit Kayaks & Tubes for Floating
9.2 out of 10, Wonderful, (21)
"We had a perfect weekend getaway on the river to celebrate and be together with enough space to spread out when needed. The house was fully stocked, the yard had plenty of space and a great fire pit. Not to mention how amazing the river fishing, tubing and relaxing was just a short walk away!"
The price is AED 1,504
AED 2,940 total
includes taxes & fees
22 Oct - 23 Oct
Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit Kayaks & Tubes for Floating
Modern Mountain Retreat w/ Deck + Hot Tub!
10.0 out of 10, Exceptional, (63)
"Quiet peaceful neighborhood. House is clean and spacious. Enjoyed relaxing on the deck, birdwatching, and admiring the Mountain View."
Modern Mountain Retreat w/ Deck + Hot Tub!
Big Sunny Family House
10.0 out of 10, Exceptional, (18)
"Six lady golfers stayed at Big Sunny and traveled to Gainesville to attend the Solheim Cup. We golfed at Shenandoah Valley Golf Course. We enjoyed the house very much. It had everything we needed. It was well supplied with all the extras! Nice to be in walking distance to restaurants and shops."
Big Sunny Family House
Linden Family Home w/ Yard < 5 Mi to Wineries!
2.0 star property
9.0 out of 10, Wonderful, (2)
"This house is perfect for a big group. The owner and neighbor were very friendly and location was great for visiting local caverns. Took about 20 mins to get to skyline caverns and 45 mins to get to Luray caverns. Front Royal town is about a 15 min drive to get supply's. House was a new listing and I did give the owner some feedback on improvements since he asked for them. Great stay and would stay again!"
Linden Family Home w/ Yard < 5 Mi to Wineries!
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (159)
"Great stay and super quiet. House is perfect."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Cozy Lakeside Homestead
10.0 out of 10, Exceptional, (173)
"This property is located about 4 miles down a country lane, with a lake near the mouth of the driveway. If you’re looking to escape society for a bit, this is the place. It rained during most of our trip, but the enclosed porch gave us plenty of space to read, play darts, and still enjoy nature. If you bring along your dog, they have beds and bowls for your use.This place had a cozy cabin feel …recommend!"
Cozy Lakeside Homestead
Luxury Panoramic Views, Private Riverfront Access, Fast Starlink WiFi, & more
10.0 out of 10, Exceptional, (37)
"Fabulous view and comfortable home. We had a wonderful time and thoroughly enjoyed our stay! Would highly recommend."
Luxury Panoramic Views, Private Riverfront Access, Fast Starlink WiFi, & more
Family Farmhouse & Huge Yard with a PRIVATE TRAIL WALK TO WINE!
10.0 out of 10, Exceptional, (42)
"We loved the grounds and the house was perfect, homey, roomy and had everything we needed. It was a short walk to the winery, there's a lovely creek in the back and we loved hanging out outside on the back patio with the fireplace as well as inside the house. There was room for everyone and so peaceful! "
Family Farmhouse & Huge Yard with a PRIVATE TRAIL WALK TO WINE!
A "home away from home" for any family size in the beautiful Shenandoah Valley!
2.0 star property
7.6 out of 10, Good, (5)
"We were visiting family in Winchester and needed a place to stay overnight for two nights with our dog. The house was very clean, had plenty of towels, and comfortable beds. We didn’t spend much time at the house, but it was good for our needs. Would stay again. "
The price is AED 400
AED 787 total
includes taxes & fees
1 Oct - 2 Oct
A "home away from home" for any family size in the beautiful Shenandoah Valley!
Overlook Mountain Cabin
9.8 out of 10, Exceptional, (153)
"The drive up the mountain to the property was fun and exciting—book this house and you'll see what I mean :) There’s ample parking too. The house was spotless, with a deck offering magnificent valley views. The sunset was beautiful, the internet was excellent, and the privacy was perfect—we didn’t want to leave! If you’re looking for a romantic spot, this is it! It's also ideal for families; the hike to the waterfall is great for kids, even if there’s no waterfall (it only flows during the rainy...
The price is AED 671
AED 1,274 total
includes taxes & fees
24 Oct - 25 Oct
Overlook Mountain Cabin
Home w/ Hot Tub Near Shenandoah Nat'l Park!
9.8 out of 10, Exceptional, (16)
"The rental was beautiful. My only complaint is the toilet paper was thin. Otherwise, it was a breathtaking location and a nice home! We enjoyed our stay! "
Home w/ Hot Tub Near Shenandoah Nat'l Park!
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
10.0 out of 10, Exceptional, (27)
"This property was well appointed and afforded my family the space and privacy to relax and enjoy each other's company, as well as the nature these grounds offered. We were very pleased with the entire property and the quick responses from the host! We would definitely stay here again!!!"
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Family Retreat w/ Deck Near Appalachian Trail!
10.0 out of 10, Exceptional, (34)
"The property description and photographs are accurate, and the hostess, Kathryn, is tremendous! This is the second stay for my wife and I, our two adult children, my mother- and father-in-law, and our three Australian Shepherds. Although hot weather and frequent thunderstorms limited outdoor activities and excursions last summer, we had such a pleasant time relaxing and enjoying the property's indoor amenities that we decided to come back again this year. With fantastic weather the entire...
Family Retreat w/ Deck Near Appalachian Trail!
Idyllic Mtn Retreat w/ Hot Tub Near Shenandoah NP!
9.8 out of 10, Exceptional, (35)
"Overall a wonderful stay. We had 12 adults for a get long weekend away. All were very comfortable. Good time was had by all."
Idyllic Mtn Retreat w/ Hot Tub Near Shenandoah NP!
Chic Front Royal Retreat Near Shenandoah River!
10.0 out of 10, Exceptional, (10)
"The description and pictures of this house are very accurate. It was clean and one of the better houses we've stayed in, especially since it is pet-friendly. It is small, but it was perfect for just the two of us. The Downsides: 1. As others mentioned, the sofa is not very comfortable. 2. There are no TVs in the bedrooms. 3. The steps are steep and the treads slope toward you some. I wouldn't wear socks and come down them and if you aren't used to stairs at all, be careful. I wouldn't feel...
Chic Front Royal Retreat Near Shenandoah River!
Clouds Mountain Cabin
9.4 out of 10, Exceptional, (14)
"We had a very quiet nice stay it was nice to have the woods where we could walk the dogs. The drive up was a little difficult even with four wheel drive but definitely worth the view "
Clouds Mountain Cabin
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Other property types in Middletown

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
9.8 out of 10, Exceptional, (281)
"Once again…. a wonderful, peaceful time! We brought our dog with us this time and he had a blast! Toured some wineries and just a short drive for some amazing food. Coffee on the porch and outside fires at night are the best. Already booked next year to come back with friends! "
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Mountain Views, River Frontage & HotTub + Country!
10.0 out of 10, Exceptional, (15)
"Nice place to relax , close to the river. We enjoyed it. "
Mountain Views, River Frontage & HotTub + Country!
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
10.0 out of 10, Exceptional, (347)
"Great spot for our girls getaway! Very remote with fantastic views. Front deck was wonderful for morning coffee and sunset watching! Definitely requires a truck or SUV for the road up. Lots of extra towels and plenty of space for all! Great spot! "
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
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.