A large house in a field with a cloudy sky.

Holiday Rentals in Middletown

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (14 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
The price is €165
includes taxes & fees
28 Sept - 29 Sept
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, (50 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.
The price is €276
includes taxes & fees
28 Sept - 29 Sept
Newly renovated Farm cottage with Mountain views
A wooden deck with white railings and a covered porch area.

3. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (42 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is €199
includes taxes & fees
28 Sept - 29 Sept
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.

4. 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
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is €202
includes taxes & fees
29 Sept - 30 Sept
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
A bedroom with a bed, bedside table, lamp, and a window with curtains.

5. 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, (10 reviews)
"We had a wonderful 10-day stay with our dogs at this beautiful property. The area is great, with quick access to many things. There are many really nice, small details about the home that we enjoyed. The large table was great for our 3000-piece puzzle, and the dogs enjoyed running around the property and down by the creek. Everything was very clean, and the kitchen, although low on cooking supplies, was very nice for cooking our meals. Sadly, it rained almost every day, but we were able to enjoy...
United States
Brian F.
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A house with a fire pit in the foreground and a deck with string lights in the background.

6. The Haven at Turkey Run • Hot Tub, Fire Pit, Games

The Haven at Turkey Run • Hot Tub, Fire Pit, Games
Strasburg
10.0 out of 10, Exceptional, (18 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 price is €434
includes taxes & fees
20 Oct - 21 Oct
The Haven at Turkey Run • Hot Tub, Fire Pit, Games
A hot tub with a view of a forest and a sunset.

7. 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.
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A cozy cabin interior with a large gray sectional sofa, a fireplace, and wooden paneling.

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

Waterfront cabin w/fireplace, hot tub & BBQ grill
Maurertown
10.0 out of 10, Exceptional, (3 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 €303
includes taxes & fees
29 Sept - 30 Sept
Waterfront cabin w/fireplace, hot tub & BBQ grill
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

9. 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 €377
includes taxes & fees
29 Sept - 30 Sept
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A two-story house with a balcony, string lights, and a swing.

10. Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
Cozy A frame cabin in quaint Front Royal. Dog friendly
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

11. 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, (44 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
The price is €194
includes taxes & fees
4 Oct - 5 Oct
Blue Mountain Cabin, secluded, perfect for couples, near main road
A wooden deck with a hot tub, outdoor furniture, and a view of trees.

12. Skyland Hideaway | Mountain Cabin w/ Hot Tub

Skyland Hideaway | Mountain Cabin w/ Hot Tub
Linden
9.6 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay! The house was lovely and accommodating. We will definitely be back!"
United States
Amanda B.
The price is €396
includes taxes & fees
12 Oct - 13 Oct
Skyland Hideaway | Mountain Cabin w/ Hot Tub
A log cabin interior with a cozy living room, a kitchen in the background, and a staircase leading to an upper level.

13. Cozy Log Cabin w Porch, Fire Pit, Games & River

Cozy Log Cabin w Porch, Fire Pit, Games & River
Maurertown
9.6 out of 10, Exceptional, (46 reviews)
"Wonderful cabin, had a great time! "
United States
Katherine R.
The price is €437
includes taxes & fees
26 Oct - 27 Oct
Cozy Log Cabin w Porch, Fire Pit, Games & River
A cozy living room with a stone fireplace, leather sofas, and a large TV.

14. Delicious Cabin • Wine Country Retreat w/ Hot Tub

Delicious Cabin • Wine Country Retreat w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (18 reviews)
"Property and cabin was very clean and well stocked. Location was great to get to wineries. We saw deer and fox in the back yard, very peaceful."
United States
Edward
Delicious Cabin • Wine Country Retreat w/ Hot Tub
A stainless steel barbecue grill with four burners, positioned against a concrete wall with a wooden staircase in the background.

15. The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (23 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
The price is €361
includes taxes & fees
30 Sept - 1 Oct
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

16. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
10.0 out of 10, Exceptional, (1 review)
"Great location. Great quiet atmosphere. Just one little thing - the steps are steep; so just something to be aware of."
United States
David S.
The price is €407
includes taxes & fees
8 Oct - 9 Oct
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
A wooden deck with a swing, surrounded by trees.

17. 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, (39 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 €334
includes taxes & fees
6 Oct - 7 Oct
Private Cabin in the woods w/ firepit right next to Shenandoah River
A wooden deck with a hot tub, steps, and a view of a forest.

18. The Foxwood Cabin | Hot Tub, Screened Porch, Grill

The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"Excellent stay. Very quiet and private. The property was very clean, had all of the amenities needed. Very comfortable and homey. The only thing you need to be aware of is that the USPS does not deliver to the address, Amazon will have the post office hold it in Front Royal."
United States
Roland C.
The price is €412
includes taxes & fees
29 Sept - 30 Sept
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

19. 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
10.0 out of 10, Exceptional, (2 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 €235
includes taxes & fees
29 Sept - 30 Sept
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A modern kitchen with a black countertop, wooden dining table, and a view of the outdoors through large sliding glass doors.

20. Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
9.8 out of 10, Exceptional, (36 reviews)
"It was a great place to stay and very clean."
United States
Chynna V.
The price is €382
includes taxes & fees
28 Sept - 29 Sept
Mountain cabin near national park & wineries
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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"The room was very comfortable. Uno's was a wonderful place to eat!"
Carol 1-night trip
Posted less than an hour ago
The George Washington Hotel, A Wyndham Grand Hotel

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 €194 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.