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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (121)
"Good location "
Countryside Cabin with Mountain Views near Surreybrooke Gardens

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

9.6 out of 10, Exceptional, (104)
"Our weekend cabin stay was wonderful. The safe neighborhood was quite and peaceful. Its location near nature and the city was just perfect. The cozy cabin was clean and comfy. We loved Gambrill State Park and downtown Frederick didn't disappoint as well."
The price is NZ$371
includes taxes & fees
13 Oct - 14 Oct
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

9.4 out of 10, Exceptional, (17)
"Small basement apartment had all we needed and wanted. Wonderful location. "
The price is NZ$320
includes taxes & fees
8 Oct - 9 Oct
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (128)
"Beautiful location right on the Potomac River."
RIVERKEEPER INN, Waterfront Property on the Potomac River

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (61)
"We truly loved this location and definitely will be back!"
The price is NZ$180
includes taxes & fees
20 Oct - 21 Oct
❤️ Secluded 1940s Romantic Tiny House on the River

The Oculus - Huge Cabin with a Hot Tub!

9.6 out of 10, Exceptional, (24)
"The place was big and very roomy and comfortable. Very clean .. very nice. "
The price is NZ$749
includes taxes & fees
14 Oct - 15 Oct
The Oculus - Huge Cabin with a Hot Tub!

Antietam Creek - Quiet 2 Bedroom Cabin

9.4 out of 10, Exceptional, (85)
"I loved the trip to that cabin, one of the most wonderful things"
The price is NZ$568
includes taxes & fees
13 Oct - 14 Oct
Antietam Creek - Quiet 2 Bedroom Cabin

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (132)
"Wonderful stay in a historic home within walking distance of so much American history and so many trails. Would definitely stay here again."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Enchanting Cottage, walk to Downtown Harpers Ferry

9.6 out of 10, Exceptional, (41)
"This place was perfect for our one-night stay in Harpers Ferry. Its location is in easy walking distance of the main sites. The house is old but charming. "
The price is NZ$670
includes taxes & fees
5 Nov - 6 Nov
Enchanting Cottage, walk to Downtown Harpers Ferry

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (100)
"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."
The price is NZ$973
includes taxes & fees
20 Oct - 21 Oct
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

10.0 out of 10, Exceptional, (75)
"Wonderful view from the sunroom. Peaceful and rejuvenating stay in this welcoming home. "
The price is NZ$474
includes taxes & fees
8 Oct - 9 Oct
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

9.4 out of 10, Exceptional, (106)
"Great little farm house in a quaint little town "
The price is NZ$505
includes taxes & fees
15 Oct - 16 Oct
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Blue Ridge Getaway - Sunset Views, A.T. Access

10.0 out of 10, Exceptional, (59)
"My girlfriend and I had a wonderful weekend escaping the hustle and bustle of the city. The view was spectacular and the property was perfect!"
The price is NZ$624
includes taxes & fees
8 Oct - 9 Oct
Blue Ridge Getaway - Sunset Views, A.T. Access

Luxury Getaway on The Potomac

9.8 out of 10, Exceptional, (19)
"We had 15 family members and friends staying there for 4 days. It was very comfortable and the kitchen is quite luxurious! Be aware that it's way out in the country, which was exactly what I wanted!Melissa was very responsive to our questions.Only issue we had was that the kitchen wasn't super clean (empty drawers had crumbs, microwave wasn't clean), but not bad enough to complain."
Luxury Getaway on The Potomac

Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

9.2 out of 10, Wonderful, (61)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
The price is NZ$479
includes taxes & fees
28 Oct - 29 Oct
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

8.4 out of 10, Very good, (24)
"This house"
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

9.2 out of 10, Wonderful, (12)
"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."
The price is NZ$735
includes taxes & fees
8 Oct - 9 Oct
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

9.8 out of 10, Exceptional, (23)
"Loved this home in the riverfront! Perfect Fourth of July Getaway for the whole family. "
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

Secluded Cabin a Stone's Throw From the A.T.!

10.0 out of 10, Exceptional, (33)
"We enjoyed the beautiful views and the house had everything we wanted."
The price is NZ$673
includes taxes & fees
14 Oct - 15 Oct
Secluded Cabin a Stone's Throw From the A.T.!

Wild And Wonderful Silos

9.6 out of 10, Exceptional, (7)
"Heated mattress was the best. Thank you! "
The price is NZ$506
includes taxes & fees
8 Oct - 9 Oct
Wild And Wonderful Silos
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

Find out more about Middletown

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 favorite 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 depends 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 NZ$180 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 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. Middletown is known for its golf courses and riverfront. Make sure you have time to check out the entertainment choices while you're in the area.

What are some of the best holiday rentals that Middletown has to offer?

Enchanting Cottage, walk to Downtown Harpers Ferry: This holiday home rental outside of Middletown is located in the city centre, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Middletown?

Expedia has 5 holiday rentals for your stay in Middletown.

What can I see and do in Middletown?

While exploring the area, visit family-friendly sights like Catoctin Wildlife Preserve and Zoo, or get outside and enjoy nature at Baker Park. Other places in town to visit include Maryland National Golf Club and South Mountain State Park.

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.