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

Middletown Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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 AU$264
includes taxes & fees
22 Nov - 23 Nov
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A covered outdoor seating area with a sofa, a small table, and a chair.

2. 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)
"Loved the house and privacy it provided. Relaxing getaway and it was furnished nicely. Slippers and robes added an extra touch. Communication was stellar."
United States
Rebekah G.
The price is AU$601
includes taxes & fees
3 Nov - 4 Nov
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A garden with a wooden swing set and a circular seating area.

3. 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.
The price is AU$452
includes taxes & fees
25 Oct - 26 Oct
Newly renovated Farm cottage with Mountain views
A wooden deck with white railings and a covered porch area.

4. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (46 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is AU$324
includes taxes & fees
2 Nov - 3 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.

5. 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.
The price is AU$324
includes taxes & fees
27 Oct - 28 Oct
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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, 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, (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 AU$706
includes taxes & fees
4 Nov - 5 Nov
The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6
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.
The price is AU$501
includes taxes & fees
9 Nov - 10 Nov
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, (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 AU$475
includes taxes & fees
4 Nov - 5 Nov
Waterfront cabin w/fireplace, hot tub & BBQ grill
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

9. The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is AU$357
includes taxes & fees
28 Oct - 29 Oct
The Queen of Winchester Three Bedroom with Upper Level Deck
A cabin with a porch, wooden steps, and a small table and chair.

10. Mountain Retreat w/ Loft, Fire Pit, & Grill

Mountain Retreat w/ Loft, Fire Pit, & Grill
Delray
9.2 out of 10, Wonderful, (11 reviews)
"Clean and as advertised. Gravel road was fine for most vehicles as long as they have a little clearance"
United States
Rex W.
The price is AU$327
includes taxes & fees
26 Oct - 27 Oct
Mountain Retreat w/ Loft, Fire Pit, & Grill
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

11. 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 AU$607
includes taxes & fees
3 Nov - 4 Nov
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A two-story house with a balcony, string lights, and a swing.

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

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
9.4 out of 10, Exceptional, (9 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
The price is AU$403
includes taxes & fees
2 Nov - 3 Nov
Cozy A frame cabin in quaint Front Royal. Dog friendly
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

13. Pool Table, Fireplace & Deck near Shenandoah Park

Pool Table, Fireplace & Deck near Shenandoah Park
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Home was clean and looked like it had recently been remodeled/updated. The host was very responsive and when the oven wasn't working properly, they went to Lowes and purchased a new one immediately! Made our short trip much easier not having to eat out or find a last minute option for our kids/babysitter on Friday evening. We were only in town from Thursday-Sunday, and it was perfect for the 5 of us. The pool table was a fun addition for the kids. The only minor complaint I have is that I wish I...
United States
Crystal H.
The price is AU$809
includes taxes & fees
2 Nov - 3 Nov
Pool Table, Fireplace & Deck near Shenandoah Park
A wooden deck with a swing, surrounded by trees.

14. 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, (41 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.
Private Cabin in the woods w/ firepit right next to Shenandoah River
A gravel path leading through a wooded area with a fire pit and chairs set up for outdoor seating.

15. Rivah Retreat -River Front- Fishing -Hot tub

Rivah Retreat -River Front- Fishing -Hot tub
Woodstock
10.0 out of 10, Exceptional, (32 reviews)
"It is a great place for a getaway. The place is very clean and very accommodating. I loved spending the afternoon at the river We would come back here again."
United States
Ahmed N.
The price is AU$402
includes taxes & fees
3 Nov - 4 Nov
Rivah Retreat -River Front- Fishing -Hot tub
A living room with a fireplace, a television mounted above it, and a large window with a view of trees.

16. NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
9.4 out of 10, Exceptional, (3 reviews)
"We were staying at the schoolhouse to go hiking and ride bikes. They house has been tastefully decorated. I enjoyed the quite community and the listening to the tree frogs at night. Front Royal has a few things you can enjoy such as the movie theatre, bakery and state park. I would highly recommend this propery."
United States
Suzanne J.
The price is AU$469
includes taxes & fees
9 Nov - 10 Nov
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
A house by a clear stream with a wooden bridge.

17. Peaceful Retreat on Creekside

Peaceful Retreat on Creekside
Edinburg
9.0 out of 10, Wonderful, (18 reviews)
"Amazing location that was perfect for a weekend getaway! The creek was so peaceful and water views from the deck were amazing! "
United States
Richard D.
The price is AU$313
includes taxes & fees
2 Nov - 3 Nov
Peaceful Retreat on Creekside
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

18. 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, (2 reviews)
"Really wonderful cabin. Everything was very clean and the house was super cute. Amenities were great. Would stay here again!!"
United States
Andrew G.
The price is AU$645
includes taxes & fees
3 Nov - 4 Nov
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
A hot tub with a view of a snowy landscape and trees.

19. "Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Rileyville
10.0 out of 10, Exceptional, (375 reviews)
"Amazing location and perfect get away for two"
United States
Heather R.
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

20. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
The price is AU$543
includes taxes & fees
28 Oct - 29 Oct
The Honeymoon Cabin | Private Couple's Retreat w/ 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.
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Top Middletown Hotel Reviews

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

8/10 Good
"It was a nice hotel."
Eric 1-night trip
Posted 8 hours ago
Comfort Inn & Suites Winchester

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, 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 favourite 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 depend 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 AU$324 per night. Entering your travel dates in the search wizard might find you 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.