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

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Middletown vacation rentals

A garden with a wooden swing set and a circular seating area.

1. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (56 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 AED 588
AED 1,191 total
includes taxes & fees
18 Oct - 19 Oct
Newly renovated Farm cottage with Mountain views
A wooden deck with white railings and a covered porch area.

2. 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 AED 496
AED 818 total
includes taxes & fees
18 Oct - 19 Oct
Mountain View Bungalow in Front Royal
A bedroom with a bed, bedside table, lamp, and a window with curtains.

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)
"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 AED 603
AED 1,341 total
includes taxes & fees
26 Oct - 27 Oct
Chalet w/Hot Tub, Deck, Game Room & EV Charger
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 AED 545
AED 825 total
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.

5. 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 AED 790
AED 1,851 total
includes taxes & fees
2 Nov - 3 Nov
The Haven at Turkey Run • Hot Tub, Fire Pit, Games
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

6. 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 AED 1,074
AED 1,601 total
includes taxes & fees
26 Oct - 27 Oct
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A cozy cabin interior with a large gray sectional sofa, a fireplace, and wooden paneling.

7. 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 AED 608
AED 1,272 total
includes taxes & fees
4 Nov - 5 Nov
Waterfront cabin w/fireplace, hot tub & BBQ grill
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

8. 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, (4 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 AED 547
AED 965 total
includes taxes & fees
19 Oct - 20 Oct
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

9. 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 AED 653
AED 1,907 total
includes taxes & fees
19 Oct - 20 Oct
Pool Table, Fireplace & Deck near Shenandoah Park
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, (32 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 AED 507
AED 1,000 total
includes taxes & fees
3 Nov - 4 Nov
Rivah Retreat -River Front- Fishing -Hot tub
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11. 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.
The price is AED 1,194
AED 2,163 total
includes taxes & fees
20 Oct - 21 Oct
Sunset Haven - 10 min from Skyline Drive. Hot Tub
A wooden cabin with a porch, surrounded by trees and a gravel path.

12. 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 AED 643
AED 1,244 total
includes taxes & fees
25 Oct - 26 Oct
The Grape Escape - A-Frame Cabin
A cabin with a porch, wooden steps, and a small table and chair.

13. 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 AED 382
AED 826 total
includes taxes & fees
19 Oct - 20 Oct
Mountain Retreat w/ Loft, Fire Pit, & Grill
A two-story house with a balcony, string lights, and a swing.

14. 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 AED 533
AED 1,037 total
includes taxes & fees
1 Nov - 2 Nov
Cozy A frame cabin in quaint Front Royal. Dog friendly
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 AED 525
AED 1,349 total
includes taxes & fees
9 Nov - 10 Nov
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A two-story house with a front porch, a mailbox, and a number plate.

16. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (10 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 AED 727
AED 1,294 total
includes taxes & fees
18 Oct - 19 Oct
Cameron Charmer pristine downtown apt with double master suites
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, (45 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 AED 771
AED 960 total
includes taxes & fees
18 Oct - 19 Oct
Blue Mountain Cabin, secluded, perfect for couples, near main road
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

18. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (14 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is AED 716
AED 924 total
includes taxes & fees
18 Oct - 19 Oct
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
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 AED 514
AED 1,426 total
includes taxes & fees
3 Nov - 4 Nov
The Honeymoon Cabin | Private Couple's Retreat 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.

20. 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, (47 reviews)
"Wonderful cabin, had a great time! "
United States
Katherine R.
The price is AED 682
AED 1,646 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Log Cabin w Porch, Fire Pit, Games & River
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

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park

8/10 Good
"Clean room, nice staff, and everything was orderly. For the price, its ok."
Hyo Jun 1-night trip
Posted 1 hour ago
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, you can find vacation rentals near well known sights in Middletown, or you can go with a secluded option if you're looking for relaxation. Our travelers 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 vacation home rentals that Middletown has to offer?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This vacation home rental near Middletown is located in a rural location and has a fireplace, a balcony, and a barbecue grill 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 vacation with amenities like 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 vacation rental in Middletown like?

Vacation rentals are private properties where you can stay for a couple of days or more in Middletown. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for small groups.