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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Welcome to the Ladybug Retreat!

The price is AU$570
includes taxes & fees
20 July - 21 July
Welcome to the Ladybug Retreat!

Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

9.0 out of 10, Wonderful, (24)
"Everything was as described. We had a lovely weekend relaxing under the stars in the hot tub and spending time with family in the Shenandoah Valley. We can't wait to come back to this oasis!"
The price is AU$468
includes taxes & fees
14 July - 15 July
Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

10.0 out of 10, Exceptional, (14)
"View was great, was pretty isolated from other houses in the area, and cute decor. Very comfortable stay. "
The price is AU$583
includes taxes & fees
13 July - 14 July
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

Charming Private Suite in Historic Colonial House – right beside from The Inn!

10.0 out of 10, Exceptional, (14)
"an excellent option if dining at the INN"
The price is AU$357
includes taxes & fees
4 Aug - 5 Aug
Charming Private Suite in Historic Colonial House – right beside from The Inn!

Colonial 3BR Home • Walk to The Inn • Great Location • Fast Wi-Fi

10.0 out of 10, Exceptional, (119)
"The house was comfy and well appointed. The owners have made every effort to cover whatever you might need while staying in the home. "
The price is AU$489
includes taxes & fees
4 Aug - 5 Aug
Colonial 3BR Home • Walk to The Inn • Great Location • Fast Wi-Fi

Mint Cottage at Little Washington - a modern, spacious retreat with a view

10.0 out of 10, Exceptional, (6)
"Mint Cottage is a gem. Its spacious, beautifully furnished, and a great place to stay to explore Shenandoah National Park and its environs"
The price is AU$670
includes taxes & fees
13 July - 14 July
Mint Cottage at Little Washington - a modern, spacious retreat with a view

Pirate's Cove River Front Oasis, Group Adventure

10.0 out of 10, Exceptional, (4)
"The place is amazing and the host was quick with the response! Me and my family had a great time and will be returning guests!!!"
The price is AU$2,222
includes taxes & fees
14 July - 15 July
Pirate's Cove River Front Oasis, Group Adventure

Windy Knoll Adventure!

8.8 out of 10, Excellent, (3)
"Great stay and very accommodating for outings/get together with friends. We loved the fire pit area. Great views of the Shenandoah river as well."
The price is AU$610
includes taxes & fees
20 July - 21 July
Windy Knoll Adventure!

Juliana Spa Suite - Luxury Main Floor

9.0 out of 10, Wonderful, (2)
"Very clean.. Great location! "
The price is AU$232
includes taxes & fees
14 July - 15 July
Juliana Spa Suite - Luxury Main Floor

Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

10.0 out of 10, Exceptional, (13)
"Great proximity to Shenandoah N P ! Comfortable beds! Appreciated the host let us check in early."
The price is AU$582
includes taxes & fees
13 July - 14 July
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

Big Sunny Family House

10.0 out of 10, Exceptional, (35)
"The house was clean, the kitchen had sufficient utensils and supplies, the location was close to restaurants."
The price is AU$760
includes taxes & fees
22 July - 23 July
Big Sunny Family House

Cameron Charmer pristine downtown apt with double master suites

9.0 out of 10, Wonderful, (2)
"Property is freshly renovated, very clean, nicely appointed. There was a pervasive musty/mildewy smell throughout the unit, i expect there is a leak somewhere from the renovation. Also, while well appointed, there were no hospitality items...usually there is at least coffee/tea, especially at this price point. We enjoyed our stay and the location was convenient to the theater and the downtown area."
The price is AU$535
includes taxes & fees
14 July - 15 July
Cameron Charmer pristine downtown apt with double master suites

Sunset Haven - 10 min from Skyline Drive. Hot Tub

9.8 out of 10, Exceptional, (7)
"Really enjoyed our stay. The house was lovely with amazing views. The bar and game room were fun. Lots of detail and thought were put into making this house feel like home. We will definitely be back!"
The price is AU$1,207
includes taxes & fees
21 July - 22 July
Sunset Haven - 10 min from Skyline Drive. Hot Tub

Newly renovated Farm cottage with Mountain views

9.8 out of 10, Exceptional, (30)
"The cottage was very charming and outfitted for maximum relaxation. We would definitely stay there again."
The price is AU$501
includes taxes & fees
13 July - 14 July
Newly renovated Farm cottage with Mountain views

River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi

10.0 out of 10, Exceptional, (51)
"Very well maintained property. "
The price is AU$725
includes taxes & fees
3 Aug - 4 Aug
River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi

Ridgeview Mountain Cabin

9.4 out of 10, Exceptional, (41)
"Very well maintained, clean, gorgeous views. We'll be back next year."
The price is AU$543
includes taxes & fees
13 July - 14 July
Ridgeview Mountain Cabin

Overlook Mountain Cabin

9.8 out of 10, Exceptional, (159)
"Beautiful mountain view! The trip was nice and beautiful! I love a good cozy vibe in the mountains! Communication with property manger was very excellent customer service! "
The price is AU$562
includes taxes & fees
21 July - 22 July
Overlook Mountain Cabin

Shenandoah Mountain Cabin

10.0 out of 10, Exceptional, (14)
"This place is amazing! So clean and comfortable. Drive up to the cabin is very bumpy but so very worth it. "
The price is AU$582
includes taxes & fees
21 July - 22 July
Shenandoah Mountain Cabin

Hideaway Mountain Cabin

10.0 out of 10, Exceptional, (11)
"Hideaway cabin was the perfect mountain getaway. My husband and I stayed here with our two dogs and it was so cozy and had everything we needed. The cabin was clean, and had all the essentials for cooking. The views are amazing and we loved using the wood fire stove. We took our dogs to the waterfall hike and they had a blast. Definitely recommend staying here! "
The price is AU$582
includes taxes & fees
25 July - 26 July
Hideaway Mountain Cabin
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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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?

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 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.