A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

Holiday Rentals in Middletown

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Middletown holiday rentals

A hot tub in front of a wooden cabin with a tree in the background.

1. Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (15 reviews)
"This tiny house was an absolute dream to stay at! Jen is very attentive to detail- everything from the decor to the thoughtful welcome basket and supplying a feed bucket for the farm animals was perfection. My kids requested our next vacation just be there instead! "
United States
Laura H.
The price is €158
includes taxes & fees
22 Nov - 23 Nov
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A garden with a wooden swing set and a circular seating area.

2. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (57 reviews)
"We enjoyed our stay here. The property was lovely and the house was nicely stocked and decorated. We will definitely stay again when in the area!"
United States
Marsha N.
Newly renovated Farm cottage with Mountain views
A modern, dark-colored triangular building with a balcony and outdoor seating area.

3. Chalet w/Hot Tub, Deck, Game Room & EV Charger

Chalet w/Hot Tub, Deck, Game Room & EV Charger
Stephens City
10.0 out of 10, Exceptional, (11 reviews)
"A wonderful place to relax and enjoy being with family or friends, with lots of room for the dogs to run and play!"
United States
Laura V.
The price is €334
includes taxes & fees
30 Nov - 1 Dec
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

4. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (16 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
The price is €371
includes taxes & fees
12 Nov - 13 Nov
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A house with a fire pit in the foreground and a deck with string lights in the background.

5. The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6

The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6
Strasburg
10.0 out of 10, Exceptional, (20 reviews)
"This was the ideal isolated cabin for our trip to Northern Virginia. It was clean, well laid out, and very well stocked with everything you need. I highly recommend staying here if you are in the area!"
United States
Paul S.
The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6
A wooden deck with white railings and a covered porch area.

6. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (51 reviews)
"It was great and beautiful place to staying. Thanks for hospitality"
United States
Onon
The price is €192
includes taxes & fees
22 Nov - 23 Nov
Mountain View Bungalow in Front Royal
A cozy living room with a grey sofa, patterned cushions, a small side table with a lamp, and decorative vases.

7. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.0 out of 10, Wonderful, (18 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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8. Sunset Haven - 10 min from Skyline Drive. Hot Tub

Sunset Haven - 10 min from Skyline Drive. Hot Tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"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!"
United States
Laura D.
Sunset Haven - 10 min from Skyline Drive. Hot Tub
A cozy cabin interior with a large gray sectional sofa, a fireplace, and wooden paneling.

9. Waterfront cabin w/fireplace, hot tub & BBQ grill

Waterfront cabin w/fireplace, hot tub & BBQ grill
Maurertown
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful time. The cabin was well stocked and we had everything we could have possibly needed. The hot tub was so nice and relaxing. We will definitely be coming back to this cabin. We loved the area and enjoyed the town. "
United States
DONNA M.
The price is €306
includes taxes & fees
16 Nov - 17 Nov
Waterfront cabin w/fireplace, hot tub & BBQ grill
A modern living room with a sofa, a coffee table, and a lamp. There is a kitchen area in the background with cabinets and a painting on the wall.

10. Executive Suites

Executive Suites
3.0 star property
Winchester
The price is €255
includes taxes & fees
12 Nov - 13 Nov
Executive Suites
A wooden deck with a swing, surrounded by trees.

11. Private Cabin in the woods w/ firepit right next to Shenandoah River

Private Cabin in the woods w/ firepit right next to Shenandoah River
Bentonville
10.0 out of 10, Exceptional, (42 reviews)
"Had a great stay, host was quick to answer questions, available for communication and extremely kind. Cabin was clean and comfortable, it’s going on our list of places to come back to."
United States
Isaac S.
The price is €323
includes taxes & fees
12 Nov - 13 Nov
Private Cabin in the woods w/ firepit right next to Shenandoah River
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

12. Pool Table, Fireplace & Deck near Shenandoah Park

Pool Table, Fireplace & Deck near Shenandoah Park
Front Royal
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Very quiet neighborhood good for walking"
United States
tom c.
Pool Table, Fireplace & Deck near Shenandoah Park
A two-story house with a front porch, a mailbox, and a number plate.

13. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.8 out of 10, Exceptional, (11 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
The price is €303
includes taxes & fees
12 Nov - 13 Nov
Cameron Charmer pristine downtown apt with double master suites
A covered outdoor area with a fire pit, seating, and a view of the landscape.

14. Mountaintop Cottage | Private Hot Tub

Mountaintop Cottage | Private Hot Tub
Front Royal
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay, house was beautiful and clean. Coffee in the morning with the deer was awesome. Love the neighborhood cat Luna."
United States
Kevin D.
The price is €536
includes taxes & fees
12 Nov - 13 Nov
Mountaintop Cottage | Private Hot Tub
A hot tub with a view of a forest and a sunset.

15. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.6 out of 10, Exceptional, (14 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
The price is €288
includes taxes & fees
17 Nov - 18 Nov
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

16. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
The price is €227
includes taxes & fees
10 Dec - 11 Dec
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

17. Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (47 reviews)
"Nice cabin for couples. The bed was comfy and had all basic necessities for making meals. We will definitely stay again."
United States
Carla M.
The price is €227
includes taxes & fees
12 Nov - 13 Nov
Blue Mountain Cabin, secluded, perfect for couples, near main road
A hot tub on an outdoor deck with a view of trees and hills.

18. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is €595
includes taxes & fees
15 Nov - 16 Nov
Mountain View Cottage | Hot Tub & Game Room
A modern living room with a fireplace, a large sofa, a coffee table, and a TV mounted on the wall.

19. Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!

Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
3.0 star property
Luray
The price is €293
includes taxes & fees
12 Nov - 13 Nov
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
A cozy living room with a stone fireplace, leather sofas, and a large TV.

20. Delicious Cabin | Wine Country Hot Tub, Game Room + Screened Porch

Delicious Cabin | Wine Country Hot Tub, Game Room + Screened Porch
Linden
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful property in a beautiful location! Great amenities!"
United States
Joan M.
The price is €436
includes taxes & fees
6 Dec - 7 Dec
Delicious Cabin | Wine Country Hot Tub, Game Room + Screened Porch
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

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent
"One night stay. All was great!"
Stephen 1-night trip
Posted 2 hours ago
Ramada by Wyndham Strasburg/Shenandoah Valley

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middletown holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as €192 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday 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 holiday.

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 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?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This holiday home rental outside of Middletown is located in a rural location, 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Middletown?

Shenandoah River and Cedar Creek and Belle Grove National Historical Park are a couple of lovely local spots to get outside and enjoy nature. While here, Belle Grove Plantation and Jackson's Chase Golf Course 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.