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

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, (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 HK$1,136
HK$1,439 total
includes taxes & fees
22 Sept - 23 Sept
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, (49 reviews)
"What an absolutely lovely and peaceful place to stay! We had a wonderful visit. "
United States
Stephanie T.
The price is HK$1,128
HK$2,412 total
includes taxes & fees
31 Aug - 1 Sept
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, (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 HK$1,351
HK$2,726 total
includes taxes & fees
15 Sept - 16 Sept
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

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 HK$2,292
HK$3,415 total
includes taxes & fees
26 Aug - 27 Aug
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A wooden deck with white railings and a covered porch area.

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 HK$1,058
HK$1,744 total
includes taxes & fees
30 Aug - 31 Aug
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.

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 HK$1,164
HK$1,769 total
includes taxes & fees
26 Aug - 27 Aug
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
A modern kitchen with a black countertop, wooden dining table, and a view of the outdoors through large sliding glass doors.

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 HK$1,482
HK$3,355 total
includes taxes & fees
26 Aug - 27 Aug
Mountain cabin near national park & wineries
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

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 HK$1,489
HK$1,876 total
includes taxes & fees
3 Sept - 4 Sept
Blue Mountain Cabin, secluded, perfect for couples, near main road
A gravel path leading through a wooded area with a fire pit and chairs set up for outdoor seating.

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

Rivah Retreat -River Front- Fishing -Hot tub
Woodstock
10.0 out of 10, Exceptional, (29 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$1,207
HK$2,311 total
includes taxes & fees
3 Sept - 4 Sept
Rivah Retreat -River Front- Fishing -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 HK$1,291
HK$2,706 total
includes taxes & fees
1 Sept - 2 Sept
Waterfront cabin w/fireplace, hot tub & BBQ grill
A modern living room with a fireplace, a round coffee table, and a comfortable seating area.

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.
Indigo Blue modern open vibe on tree lined street
A wooden deck with a swing, surrounded by trees.

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, (38 reviews)
"Awesome spot…clean, cozy, private. Hosts were very responsive- can’t ask for anything more "
United States
Asim K.
The price is HK$1,168
HK$2,663 total
includes taxes & fees
9 Sept - 10 Sept
Private Cabin in the woods w/ firepit right next to Shenandoah River
A two-story house with a front porch, a mailbox, and a number plate.

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 HK$1,552
HK$2,672 total
includes taxes & fees
17 Sept - 18 Sept
Cameron Charmer pristine downtown apt with double master suites
A log cabin interior with a cozy living room, a kitchen in the background, and a staircase leading to an upper level.

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 HK$1,261
HK$3,284 total
includes taxes & fees
7 Sept - 8 Sept
Cozy Log Cabin w Porch, Fire Pit, Games & River
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

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 HK$1,160
HK$2,060 total
includes taxes & fees
21 Sept - 22 Sept
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A two-story house with a balcony, a hot tub, and a circular wooden structure.

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 HK$1,411
HK$4,071 total
includes taxes & fees
30 Aug - 31 Aug
Luxury Mountain Retreat w/ Valley Views, Hot Tub
A balcony with a view of a valley and distant mountains.

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 HK$1,489
HK$4,253 total
includes taxes & fees
26 Aug - 27 Aug
Wilderness Ridge | Private Cabin w/ Mountain Views
A spacious log cabin with a stone fireplace, large windows, a television, and a cozy seating 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 HK$1,489
HK$3,259 total
includes taxes & fees
1 Sept - 2 Sept
River Woods Retreat: Hot Tub, Hikes, 2 Fireplaces, EV
A living room with a sofa, armchair, coffee table, and a television.

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 HK$1,450
HK$2,584 total
includes taxes & fees
21 Sept - 22 Sept
Nostalgia Lane in the heart of the city
A cabin with a hot tub on a deck, surrounded by a forest.

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 HK$1,728
HK$3,566 total
includes taxes & fees
26 Aug - 27 Aug
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

Spark by Hilton Winchester

Spark by Hilton Winchester

8/10 Good
"The hotel and room were the cleanest place I have stayed at in a long time! Definitely would recommend it to anyone."
James 1-night trip
Posted 5 hours ago
Spark by Hilton 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?

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub: This holiday home rental outside of Middletown is located on a river, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.