A large house in a field with a cloudy sky.

Middletown Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 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 HK$1,138
HK$1,441 total
includes taxes & fees
20 Oct - 21 Oct
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, (55 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 HK$1,256
HK$2,562 total
includes taxes & fees
12 Oct - 13 Oct
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, (43 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is HK$1,059
HK$1,738 total
includes taxes & fees
18 Oct - 19 Oct
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
9.0 out of 10, Wonderful, (18 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is HK$1,165
HK$1,762 total
includes taxes & fees
13 Oct - 14 Oct
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, (11 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.
The price is HK$1,870
HK$3,587 total
includes taxes & fees
3 Nov - 4 Nov
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 HK$1,609
HK$3,887 total
includes taxes & fees
3 Nov - 4 Nov
The Haven at Turkey Run • Hot Tub, Fire Pit, Games
A wooden cabin with a porch, a bench, and a table.

7. Peaceful mountain cabin in charming Berryville VA - next to river and brewery

Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Berryville
10.0 out of 10, Exceptional, (3 reviews)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveller
The price is HK$589
HK$1,930 total
includes taxes & fees
18 Oct - 19 Oct
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
A cabin with a porch, wooden steps, and a small table and chair.

8. 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 HK$816
HK$1,765 total
includes taxes & fees
12 Oct - 13 Oct
Mountain Retreat w/ Loft, Fire Pit, & Grill
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

9. 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, (3 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 HK$1,161
HK$2,054 total
includes taxes & fees
12 Oct - 13 Oct
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A gravel path leading through a wooded area with a fire pit and chairs set up for outdoor seating.

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

Rivah Retreat -River Front- Fishing -Hot tub
Woodstock
10.0 out of 10, Exceptional, (31 reviews)
"This property is excellent for a secluded getaway that is still close to major attractions. The private river access is great and the host stocked the cabin as well as any property we've stayed at."
United States
Robert G.
The price is HK$1,184
HK$2,246 total
includes taxes & fees
4 Nov - 5 Nov
Rivah Retreat -River Front- Fishing -Hot tub
A two-story house with a balcony, string lights, and a swing.

11. 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, (8 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
The price is HK$1,138
HK$2,216 total
includes taxes & fees
1 Nov - 2 Nov
Cozy A frame cabin in quaint Front Royal. Dog friendly
A stainless steel barbecue grill with four burners, positioned against a concrete wall with a wooden staircase in the background.

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

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (24 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
The price is HK$1,358
HK$3,082 total
includes taxes & fees
3 Nov - 4 Nov
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
A cozy cabin interior with a large gray sectional sofa, a fireplace, and wooden paneling.

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

Waterfront cabin w/fireplace, hot tub & BBQ grill
Maurertown
10.0 out of 10, Exceptional, (4 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 HK$1,636
HK$3,160 total
includes taxes & fees
8 Nov - 9 Nov
Waterfront cabin w/fireplace, hot tub & BBQ grill
A house by a clear stream with a wooden bridge.

14. 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 HK$777
HK$1,705 total
includes taxes & fees
18 Oct - 19 Oct
Peaceful Retreat on Creekside
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

15. 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 HK$1,232
HK$3,514 total
includes taxes & fees
27 Oct - 28 Oct
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

16. 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 HK$1,714
HK$4,479 total
includes taxes & fees
18 Oct - 19 Oct
Pool Table, Fireplace & Deck near Shenandoah Park
A white building with a black door and a set of blue-painted stairs with black railings.

17. The Blue Door steps from Handley Library

The Blue Door steps from Handley Library
Old Town Winchester
5.4 out of 10, (3 reviews)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The price is HK$902
HK$1,520 total
includes taxes & fees
26 Oct - 27 Oct
The Blue Door steps from Handley Library
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

18. 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 HK$2,295
HK$3,420 total
includes taxes & fees
12 Oct - 13 Oct
Riverfront! Shenandoah River! Sleeps 4! New 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.

19. 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 HK$1,028
HK$2,960 total
includes taxes & fees
2 Nov - 3 Nov
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A wooden cabin with a porch, surrounded by trees and a gravel path.

20. The Grape Escape - A-Frame Cabin

The Grape Escape - A-Frame Cabin
Linden
10.0 out of 10, Exceptional, (26 reviews)
"This property was great for a weekend of relaxation!"
United States
Steven B.
The price is HK$1,373
HK$2,657 total
includes taxes & fees
14 Oct - 15 Oct
The Grape Escape - A-Frame 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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Top Middletown Hotel Reviews

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"The room was clean and updated. The only minor complaint is the shower didn't get as hot as I am used too. It was in a good neighborhood with lots of options for eating."
Nicholas 1-night trip
Posted 2 hours ago
Quality Inn Winchester

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middletown!

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.