Photo by Stephanie Sutton

Holiday Rentals in Middletown

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Holiday Rentals in Middletown

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (310)
"This lovely cabin was exactly what we were looking for. It's cozy with a spectacular view and the river access was perfectly scenic. "
Star view cabin-Riverfront

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (84)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

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

9.6 out of 10, Exceptional, (306)
"It was very rustic and supplies were plentiful. The cleaner went above and beyond to help me and checked on me after a bad storm. The only hassle was the security gate, but I understand the need to keep unauthorized persons off the property. It was just getting the key out opening and closing and relocking every trip out. It’s all ok. I do suggest that candles are available as the power was out one night for 3 hours and I was alone and not scared but just in darkness except for moonlight. Loved...
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

Falling Leaf Cabin With Winter River And Mountain View!

9.8 out of 10, Exceptional, (281)
"Fourth time here and it never gets old!!! absolutely gorgeous!"
Falling Leaf Cabin With Winter River And Mountain View!

Bear Valley- Riverfront with hot tub!

9.6 out of 10, Exceptional, (115)
"We thoroughly enjoyed our stay. It was very peaceful and quiet. Lots of wildlife and the view of the Shenandoah Valley River was amazing. Would definitely stay here again. "
Bear Valley- Riverfront with hot tub!

Mountain Views, River Frontage & HotTub + Country!

10.0 out of 10, Exceptional, (27)
"The cabin and property are amazing. The river is a short walk from the cabin and absolutely serene. The locals are kind and welcoming. Couldn't ask for a nicer place to relax and reconnect with mother nature. "
Mountain Views, River Frontage & HotTub + Country!

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (169)
"This was the perfect get away. The cottage was clean, comfortable, and had all the amenities we needed. "
Secluded, Cozy Cottage in the Shenandoah Valley

The Perch Riverfront Cabin - Starlink Satellite Wi-Fi

9.4 out of 10, Exceptional, (31)
"The best escape that we could use have hoped for! Beautiful views and songbird symphonies in the morning. Had sunshine and a thunderstorm to enjoy, couldn’t have been a better stay!"
The Perch Riverfront Cabin - Starlink Satellite Wi-Fi

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

9.8 out of 10, Exceptional, (283)
"Property was easy to locate and readily accessible. Did not realize property was on a mountain that had steep hills, just a fear of mine so it was more jarring for me but it may be nothing of substance for someone else who is used to country living. House itself was super cute and intimate! We loved the layout and hot tun was clean enough to the location and environment"
The price is €277
includes taxes & fees
17 Apr - 18 Apr
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

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

9.6 out of 10, Exceptional, (346)
"We enjoyed every moment. Communication with the owner was fantastic. We will recommend the cabin to friends and family"
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

Riverfront, pet friendly ! Log cabin with 2 bedrooms and loft!

10.0 out of 10, Exceptional, (263)
"Excellent location away from city life! Quiet, comfortable, relaxing."
Riverfront, pet friendly ! Log cabin with 2 bedrooms and loft!

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (39)
"We loved our stay at the cottage! Will is a wonderful host!"
Historical cottage in the town of Paris

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

10.0 out of 10, Exceptional, (309)
"My wife & I needed a break from the daily grind & this place was exactly what the doctor ordered. Highly highly recommend this place to anyone. We hope to be able to return again sometime"
The price is €259
includes taxes & fees
23 Apr - 24 Apr
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

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

9.6 out of 10, Exceptional, (55)
"Family and I loved our stay at Whistling Woods Retreat! Relax by the fire and take in the blue ridge mountains! Short drive to luray and Shenandoah national park. Tons of games and places to explore on the property for the kids. Definitely Recommend ! "
The price is €298
includes taxes & fees
4 May - 5 May
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

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

9.4 out of 10, Exceptional, (133)
"Our family thoroughly enjoyed staying here! The property was beautiful and the views are unmatched!!!!! Everything about this place was perfect. "
Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

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

9.6 out of 10, Exceptional, (103)
"The cabin was clean, comfortable, and tastefully decorated. It offered lots of amenities, all of which were in working order. I would definitely recommend it for a weekend getaway!"
Heaven's Hideaway- a perfect getaway near the Shenandoah River!

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (216)
"Beautiful home"
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

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

10.0 out of 10, Exceptional, (44)
"A home away from home! We had a fabulous stay - doing day hikes in the national park (Thornton Gap is an easy 30min drive) and spending family time cooking, playing games in the evenings. We appreciated all the nice details Diana arranged for our stay. So glad we chose this location! "
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!

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!

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

9.6 out of 10, Exceptional, (173)
"We had an extremely relaxing stay. The area is gorgeous…loved being close to the water. We brought our dog and it was great to let him run and play and just be a dog. Did have a few issues with a few appliances, but the host was super quick to bring a new remote and coffee pot. All in all we would stay again!"
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-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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Other types of properties in Middletown you may be interested in

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (386)
"Was a very fun atmosphere with and employees and also other guess very nice and friendly and excellent wings"
The price is €115
includes taxes & fees
17 Apr - 18 Apr
Wayside Inn

La Quinta Inn & Suites by Wyndham Winchester

3.0 star property
9.2 out of 10, Wonderful, (1915)
"in inf Firmin. Rima rijfijfj"
The price is €104
includes taxes & fees
13 Apr - 14 Apr
La Quinta Inn & Suites by Wyndham Winchester

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1004)
"Beautiful hotel, super easy check in, restaurant on the property is Unos Pizzeria, just one block away is Old Town and we had an enjoyable evening strolling that area after dinner. We’ve already booked another stay for ‘our stop on the way home.’"
The price is €131
includes taxes & fees
17 Apr - 18 Apr
The George Washington Hotel, A Wyndham Grand Hotel
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 holiday rental in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Middletown has to offer?

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly: This holiday home rental outside of Middletown is located on a river, and has a fireplace, a balcony and a BBQ 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 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middletown?

Choose from 3 Expedia holiday rentals in Middletown for a memorable holiday.

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, Cedar Creek Battlefield Foundation and Belle Grove Plantation are other places worth a visit.

What’s a holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.