Middletown Holiday Rentals from AU$313: Search Short-Term Rentals

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Our top choices for Middletown holiday rentals

1. Luxury tiny home farm stay on historic property with hot tub in Stephens City

Stephens City

Shawn P.

includes taxes & fees

13 Sept - 14 Sept

2. Newly renovated Farm cottage with Mountain views

Strasburg

Stephanie T.

includes taxes & fees

8 Sept - 9 Sept

3. Mountain View Bungalow in Front Royal

Front Royal

HEMANT S.

includes taxes & fees

8 Sept - 9 Sept

4. Chalet w/Hot Tub, Deck, Game Room & EV Charger

Stephens City

"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...

Brian F.

includes taxes & fees

23 Sept - 24 Sept

5. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Front Royal

Jake M.

includes taxes & fees

9 Sept - 10 Sept

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

Front Royal

Hailey

includes taxes & fees

8 Sept - 9 Sept

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

Maurertown

DONNA M.

includes taxes & fees

29 Sept - 30 Sept

8. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

Linden

Scott M.

includes taxes & fees

22 Sept - 23 Sept

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Top Middletown Hotel Reviews

Travelodge by Wyndham Winchester

8/10 Good

"The registration staff was very helpful. I expressed that I did not want a room on the wing that they have long term guests that I believe are homeless. I have been placed there in the past because I have a service dog and did not like it. I was given a much nicer room. However, stayed 3 nights and never did a housekeeper come in and empty trash or give clean towels. The outside has cigarette butts all over. We have been going to this hotel for many years, several times a year and it seems it has gone downhill which is very disappointing to me. The long term people hang out at the entrance smoking. Who wants to deal with that upon entering. I hope this review calls these issues to managements attention and they bring this hotel back to the nice place it once was."

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Perfect for our needs. Located near to family, good neighborhood located nearby for walk/run in free time. Available hot breakfast nice and filling, limited fitness room also available with a nearby indoor pool. Rooms are compact but it fit our travel needs as a couple looking for a place to sleep over the weekend perfectly. Staff were also really helpful and had our keycards ready to go immediately, our fastest recent check-in and helpful for a later evening arrival. We‘ll stay here again while in the area."

Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent

"Stayed two separate nights. As a solo traveler, I felt safe checking in and driving around the area for food, (dinner, I didn't try mexican restaurant next door but was assured by locals that it was very good) Staff were pleasant, room clean and comfortable. Breakfast was standard continental fare, nothing unexpectant. Parking was convenient. I used the gym in the morning only negative was the lack of weights available. 10lb, 20lb and 25lb only. but it was clean, unfortunately tv wasn't working but I had brought my headphones so worked for me. I would stay here again if ever in the area"

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"We chose Old Town Winchester and stayed at The George Washington Hotel as our gathering spot for High school girl friends The Hotel was beautiful ,our rooms big enough plus having a sm scale table with 2 chairs ,the bathroom very roomy,beds were very comfortable and the staff very accommodating and welcoming The amenities at the hotel met our needs perfectly ! It was really nice to be in a walkable area with many shops and restaurants ,pubs .No complaints from 5 women in our group 😁"

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

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

Middletown holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as AU$313 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday 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 holiday.

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 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.

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Check prices for these dates

Our top choices for Middletown holiday rentals

1. Luxury tiny home farm stay on historic property with hot tub in Stephens City

2. Newly renovated Farm cottage with Mountain views

3. Mountain View Bungalow in Front Royal

4. Chalet w/Hot Tub, Deck, Game Room & EV Charger

5. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

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

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

8. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

9. Cozy Log Cabin w Porch, Fire Pit, Games & River

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

11. Private Cabin in the woods w/ firepit right next to Shenandoah River

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

13. Delicious Cabin • Wine Country Retreat w/ Hot Tub

14. Downtown Apt 2 • 2BR • Near Park & River • Private

15. Downtown Apt 3 • 2BR • Near Park & River • Private

16. Downtown Apt.1 • 2BR/2BA• Near Park/River• Private

17. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

18. The Foxwood Cabin | Hot Tub, Screened Porch, Grill

19. Cozy A frame cabin in quaint Front Royal. Dog friendly

20. The Grape Escape - A-Frame Cabin

Find holiday rentals that suit your style

Top Middletown Hotel Reviews

Travelodge by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

TRU By Hilton Winchester

La Quinta Inn & Suites by Wyndham Winchester

Ramada by Wyndham Strasburg/Shenandoah Valley

Quality Inn Winchester

The George Washington Hotel, A Wyndham Grand Hotel

Courtyard by Marriott Winchester

Days Inn by Wyndham Winchester

Find out more about Middletown

Frequently asked questions

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