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Middletown Vacation Rentals

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Check prices for these dates

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

Our top choices for Middletown vacation 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 CA $203
CA $244 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $202
CA $429 total
includes taxes & fees
Sep 24 - Sep 25
Newly renovated Farm cottage with Mountain views

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, (9 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 CA $214
CA $458 total
includes taxes & fees
Sep 23 - Sep 24
Chalet w/Hot Tub, Deck, Game Room & EV Charger
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, (41 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is CA $189
CA $308 total
includes taxes & fees
Sep 27 - Sep 28
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
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is CA $208
CA $313 total
includes taxes & fees
Sep 29 - Sep 30
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, 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 CA $389
CA $817 total
includes taxes & fees
Oct 12 - Oct 13
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.

7. 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 CA $410
CA $608 total
includes taxes & fees
Sep 24 - Sep 25
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A log cabin interior with a cozy living room, a kitchen in the background, and a staircase leading to an upper level.

8. 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 CA $226
CA $586 total
includes taxes & fees
Sep 23 - Sep 24
Cozy Log Cabin w Porch, Fire Pit, Games & River
A hot tub with a view of a forest and a sunset.

9. 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.

10. 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 CA $235
CA $490 total
includes taxes & fees
Sep 29 - Sep 30
Waterfront cabin w/fireplace, hot tub & BBQ grill
A wooden cabin with a porch, surrounded by trees and a gravel path.

11. 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 CA $184
CA $380 total
includes taxes & fees
Sep 24 - Sep 25
The Grape Escape - A-Frame Cabin
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

12. 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 CA $240
CA $299 total
includes taxes & fees
Sep 23 - Sep 24
Blue Mountain Cabin, secluded, perfect for couples, near main road
A cozy living room with a stone fireplace, leather sofas, and a large TV.

13. 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
The price is CA $213
CA $602 total
includes taxes & fees
Sep 27 - Sep 28
Delicious Cabin • Wine Country Retreat w/ Hot Tub
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
10.0 out of 10, Exceptional, (7 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
The price is CA $241
CA $433 total
includes taxes & fees
Oct 19 - Oct 20
Cozy A frame cabin in quaint Front Royal. Dog friendly
A house with a deck, outdoor hot tub, and a staircase leading to a covered porch.

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 CA $225
CA $582 total
includes taxes & fees
Sep 23 - Sep 24
The Juniper Cabin • Cozy Hideaway w/ Hot Tub

16. 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 CA $456
CA $822 total
includes taxes & fees
Sep 29 - Sep 30
Sunset Haven - 10 min from Skyline Drive. Hot Tub
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

17. Golfers' Paradise: 3 Courses Nearby + Pool Table

Golfers' Paradise: 3 Courses Nearby + Pool Table
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 CA $361
CA $870 total
includes taxes & fees
Sep 24 - Sep 25
Golfers' Paradise: 3 Courses Nearby + Pool Table
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

18. 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 CA $208
CA $366 total
includes taxes & fees
Sep 24 - Sep 25
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A wooden cabin with a garage, surrounded by trees and a gravel driveway.

19. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is CA $363
CA $672 total
includes taxes & fees
Sep 29 - Sep 30
The Pond Cabin
A two-story house with a balcony, outdoor seating, and a hot tub.

20. Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6

Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
Front Royal
10.0 out of 10, Exceptional, (17 reviews)
"We loved this house and will definitely use it again. That said, the bathroom "
United States
Margaret S.
The price is CA $229
CA $625 total
includes taxes & fees
Oct 5 - Oct 6
Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"Hotel was very clean and breakfast was delicious with a lot of options"
Kailyn 1-night trip
Posted 2 hours ago
TRU By Hilton Winchester

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

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

Middletown vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown vacation rentals we have selected for you start as low as CA $308 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 vacation 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 vacation.

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 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.