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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Middletown vacation rentals

Terrace/patio

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, (13 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 ￥23,107
￥29,443 total
includes taxes & fees
Aug 31 - Sep 1
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Property grounds

2. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (50 reviews)
"What an absolutely lovely and peaceful place to stay! We had a wonderful visit. "
United States
Stephanie T.
The price is ￥22,948
￥49,042 total
includes taxes & fees
Aug 31 - Sep 1
Newly renovated Farm cottage with Mountain views
Outdoor dining

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, (8 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 ￥33,509
￥63,759 total
includes taxes & fees
Sep 13 - Sep 14
Chalet w/Hot Tub, Deck, Game Room & EV Charger
Outdoor spa tub

4. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (15 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
The price is ￥46,613
￥69,441 total
includes taxes & fees
Aug 30 - Aug 31
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Terrace/patio

5. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (37 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is ￥21,514
￥35,476 total
includes taxes & fees
Aug 30 - Aug 31
Mountain View Bungalow in Front Royal
Living area

6. 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 ￥23,665
￥35,948 total
includes taxes & fees
Aug 30 - Aug 31
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Interior

7. Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (34 reviews)
"It was a great place to stay and very clean."
United States
Chynna V.
The price is ￥30,119
￥68,201 total
includes taxes & fees
Aug 31 - Sep 1
Mountain cabin near national park & wineries
Property grounds

8. 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, (43 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
The price is ￥30,278
￥36,912 total
includes taxes & fees
Aug 30 - Aug 31
Blue Mountain Cabin, secluded, perfect for couples, near main road
Property grounds

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

Rivah Retreat -River Front- Fishing -Hot tub
Woodstock
10.0 out of 10, Exceptional, (30 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 ￥28,476
￥51,268 total
includes taxes & fees
Sep 22 - Sep 23
Rivah Retreat -River Front- Fishing -Hot tub
Living area

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 ￥26,235
￥55,006 total
includes taxes & fees
Sep 9 - Sep 10
Waterfront cabin w/fireplace, hot tub & BBQ grill
Interior

11. Indigo Blue modern open vibe on tree lined street

Indigo Blue modern open vibe on tree lined street
Winchester Historic District
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! The place was very clean and exactly as described. Michele communicated clearly and responded quickly, which made everything easy from check-in to check-out. The location was also perfect—very close to downtown and convenient to everything we wanted to do. We would definitely stay here again and highly recommend it to others!"
United States
Elaina R.
The price is ￥35,059
￥64,639 total
includes taxes & fees
Aug 30 - Aug 31
Indigo Blue modern open vibe on tree lined street
Property grounds

12. 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)
"Awesome spot…clean, cozy, private. Hosts were very responsive- can’t ask for anything more "
United States
Asim K.
The price is ￥23,745
￥54,140 total
includes taxes & fees
Sep 2 - Sep 3
Private Cabin in the woods w/ firepit right next to Shenandoah River
Exterior

13. 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, (9 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 ￥31,553
￥56,152 total
includes taxes & fees
Aug 30 - Aug 31
Cameron Charmer pristine downtown apt with double master suites
Living area

14. 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 ￥25,638
￥66,756 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Log Cabin w Porch, Fire Pit, Games & River
Living area

15. 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 ￥23,585
￥41,707 total
includes taxes & fees
Aug 30 - Aug 31
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Terrace/patio

16. Luxury Mountain Retreat w/ Valley Views, Hot Tub

Luxury Mountain Retreat w/ Valley Views, Hot Tub
Front Royal
9.4 out of 10, Exceptional, (3 reviews)
"Gorgeous views!!"
United States
Charlie R.
The price is ￥27,251
￥81,032 total
includes taxes & fees
Aug 30 - Aug 31
Luxury Mountain Retreat w/ Valley Views, Hot Tub
Property grounds

17. Wilderness Ridge | Private Cabin w/ Mountain Views

Wilderness Ridge | Private Cabin w/ Mountain Views
Linden
9.6 out of 10, Exceptional, (11 reviews)
"We had a great time and experience. "
United States
Adriane B.
The price is ￥30,278
￥86,481 total
includes taxes & fees
Sep 1 - Sep 2
Wilderness Ridge | Private Cabin w/ Mountain Views
Living area

18. River Woods Retreat: Hot Tub, Hikes, 2 Fireplaces, EV

River Woods Retreat: Hot Tub, Hikes, 2 Fireplaces, EV
Bentonville
10.0 out of 10, Exceptional, (69 reviews)
"Lovely home in quiet, rustic setting. Very relaxing stay. Great communication with owner."
United States
Mary W.
The price is ￥31,075
￥67,321 total
includes taxes & fees
Sep 9 - Sep 10
River Woods Retreat: Hot Tub, Hikes, 2 Fireplaces, EV
Living area

19. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (18 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is ￥29,482
￥53,445 total
includes taxes & fees
Aug 30 - Aug 31
Nostalgia Lane in the heart of the city
Terrace/patio

20. NEW Zen Cabin in the Clouds . Hot Tub, Wineries, Skyline

NEW Zen Cabin in the Clouds . Hot Tub, Wineries, Skyline
Front Royal
10.0 out of 10, Exceptional, (1 review)
"We stayed at this lovely cabin for a few days over the Thanksgiving holiday, and it was perfect. It was cozy, comfortable, and spotless…just the right size to feel at home. Natasha, the host, was wonderful. Even while traveling abroad, she communicated quickly and clearly, and we never had any issues reaching her.The kitchen was fully equipped for preparing meals, and every other room had everything we could possibly need. Thank you, Natasha - we’ll definitely be back!"
United States
Indira A.
The price is ￥37,290
￥75,230 total
includes taxes & fees
Aug 31 - Sep 1
NEW Zen Cabin in the Clouds . Hot Tub, Wineries, Skyline
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

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent
"The rooms were clean and well-maintained. The hotel has a convenient location to shopping and dining options. The public spaces are beautiful and comfortable. I rented a meeting room for a Celebration of Life gathering and used the hotel's catering service. The food was excellent and the staff was professional and helpful. The hotel restaurant wasn't great for breakfast, as the service was slow and the oatmeal was served undercooked. However, dinner was fine."
barbara 2-night trip
Posted less than an hour ago
DoubleTree by Hilton Front Royal Blue Ridge Shadows

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 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?

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub: This vacation home rental near Middletown is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.