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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Our top choices for Middletown holiday rentals

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (120)
"We LOVED our stay at Surrey Cabin! Quaint, clean, quiet, and the property is breathtaking! The bed was super comfortable and we had everything we needed. We will definitely be coming back! "
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 AU$276
includes taxes & fees
24 Sept - 25 Sept
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, (14)
"Small basement apartment had all we needed and wanted. Wonderful location. "
The price is AU$263
includes taxes & fees
28 Sept - 29 Sept
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

The Oculus - Huge Cabin with a Hot Tub!

9.6 out of 10, Exceptional, (23)
"This was a great place for our vacation."
The price is AU$667
includes taxes & fees
2 Oct - 3 Oct
The Oculus - Huge Cabin with a Hot Tub!

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (127)
"My 2 grandsons & I had a wonderful visit at the Riverkeeper Inn. The Riverfront is beautiful & lots of nature to enjoy. They also liked riding around on the golf cart in the neighborhood checking out the deer & birds. Very peaceful. It was a nice getaway for them being from Texas. "
RIVERKEEPER INN, Waterfront Property on the Potomac River

❤️ Secluded 1940s Romantic Tiny House on the River

9.8 out of 10, Exceptional, (60)
"We truly loved this location and definitely will be back!"
The price is AU$163
includes taxes & fees
5 Oct - 6 Oct
❤️ Secluded 1940s Romantic Tiny House on the River

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

10.0 out of 10, Exceptional, (57)
"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 AU$558
includes taxes & fees
24 Sept - 25 Sept
Blue Ridge Getaway - Sunset Views, A.T. Access

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

10.0 out of 10, Exceptional, (132)
"The house was perfect, right in the middle of historic Harper’s Ferry. We all had the best time! "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Antietam Creek - Quiet 2 Bedroom Cabin

9.4 out of 10, Exceptional, (85)
"Cool even with no AC. Key is to open windows at night let the coolness in, Close windows and coverings during daytime. Fans on continuously to circulate the air… Chefs kiss!!"
The price is AU$505
includes taxes & fees
22 Sept - 23 Sept
Antietam Creek - Quiet 2 Bedroom Cabin

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 AU$597
includes taxes & fees
22 Sept - 23 Sept
Secluded Cabin a Stone's Throw From the A.T.!

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

9.4 out of 10, Exceptional, (104)
"Great little farm house in a quaint little town "
The price is AU$454
includes taxes & fees
25 Sept - 26 Sept
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

10.0 out of 10, Exceptional, (68)
"The property was clean, quiet and the neighborhood was safe. We had a great time and tawny was a great host."
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

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

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 AU$467
includes taxes & fees
30 Sept - 1 Oct
Enchanting Cottage, walk to Downtown Harpers Ferry

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

10.0 out of 10, Exceptional, (74)
"Wonderful view from the sunroom. Peaceful and rejuvenating stay in this welcoming home. "
The price is AU$426
includes taxes & fees
22 Sept - 23 Sept
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

Charming Cabin in the Woods with River Access

9.6 out of 10, Exceptional, (33)
"Very nice rest time…"
The price is AU$459
includes taxes & fees
28 Sept - 29 Sept
Charming Cabin in the Woods with River Access

Luxury Getaway on The Potomac

9.8 out of 10, Exceptional, (17)
"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

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (31)
"Enjoyable stay, lovely location Clean comfortable home."
Waterfront property in Harpers Ferry - Private River Access

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

10.0 out of 10, Exceptional, (145)
"Wonderful house for a great weekend away"
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Lakefront Log Cabin w/ Dreamy Waterfront Patio!

2.0 star property
9.8 out of 10, Exceptional, (7)
"Beautiful property. Nice views of the lake."
The price is AU$493
includes taxes & fees
29 Sept - 30 Sept
Lakefront Log Cabin w/ Dreamy Waterfront Patio!
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 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$163 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. 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?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This holiday home rental outside of Middletown offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Middletown?

Expedia has 4 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 South Mountain State Park and Maryland National Golf Club.

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.