Middletown Holiday Rentals

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Holiday Rentals in Middletown

Cabin in Middletown

10.0 out of 10, Exceptional, (128)
"Great place to stay. Very quiet. Just wish there would have been a king size bed, otherwise loved it"
United States
Corinne R.
Countryside Cabin with Mountain Views near Surreybrooke Gardens

Cabin in Middletown

9.6 out of 10, Exceptional, (105)
"We loved it! As cute/sweet as described."
United States
Fran E.
The price is NZ$332
includes taxes & fees
26 Nov - 27 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Holiday Home in Charles Town

9.6 out of 10, Exceptional, (65)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
United States
Cherilyn M.
The price is NZ$722
includes taxes & fees
4 Dec - 5 Dec
Terra Alta - Incredible River Views and Hot Tub!

Cabin in Fairfield

10.0 out of 10, Exceptional, (312)
"Very clean and was perfect location for our golf weekend ! Thanks again … "
United States
jim h.
Think Snow! Liberty Ski Resort 5 minutes Away! Time to plan a winter getaway!

Holiday Home in Harpers Ferry

9.8 out of 10, Exceptional, (133)
"Although I never met my hostess, the cottage stay was easy to book and just as advertised. Fantastic views, well stocked kitchen, and a personal greeting on wet board. Gas fireplace was warm and cozy."
United States
Karen
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Cabin in Shepherdstown

10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is NZ$187
includes taxes & fees
1 Dec - 2 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

Apartment in Harpers Ferry

9.4 out of 10, Exceptional, (20)
"Cute little place with a cabin feel, it had everything I needed and then some. The place was very clean, the bed was very comfortable, and the shower was clean and welcome after long hiking days. "
United States
Julie B.
The price is NZ$376
includes taxes & fees
22 Nov - 23 Nov
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Cabin in Shepherdstown

9.6 out of 10, Exceptional, (39)
"My family enjoyed our stay at the cabin including having access to the river for morning coffee and playing board games in the evening after a day of tubing. The drive to the cabin was beautiful with lots of deer sightings. "
United States
Leana H.
The price is NZ$452
includes taxes & fees
4 Dec - 5 Dec
Charming Cabin in the Woods with River Access

Holiday Home in Harpers Ferry

8.2 out of 10, Very good, (29)
"Very nice. Loved the location. Arcade did not work and no propane for the fire pit but overall amazing."
United States
Terry K.
Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Cabin in Harpers Ferry

9.2 out of 10, Wonderful, (9)
"Very charming and spacious silo! Very quiet and comfortable. Highly recommend and would definitely stay again!"
United States
Lauren M.
The price is NZ$530
includes taxes & fees
24 Nov - 25 Nov
Wild And Wonderful Silos

Apartment in Brunswick

9.8 out of 10, Exceptional, (20)
"Absolutely loved staying in this historic apartment! The hosts are incredibly friendly and the area is very walkable with local food and shops within a quarter to half mile. Such a great experience here, can’t recommend it enough and can’t wait to stay again!"
United States
Alicia
The price is NZ$332
includes taxes & fees
25 Nov - 26 Nov
Beautiful, Historic, Hiking, Biking and C&O Canal

Holiday Home in Harpers Ferry

9.8 out of 10, Exceptional, (105)
"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."
United States
Debbie G.
The price is NZ$968
includes taxes & fees
24 Nov - 25 Nov
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Holiday Home in Harpers Ferry

9.6 out of 10, Exceptional, (101)
"The house was beyond expectations."
United States
Eddie J.
The price is NZ$735
includes taxes & fees
1 Dec - 2 Dec
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Cottage in Harper's Ferry

9.4 out of 10, Exceptional, (131)
"Beautiful location right on the Potomac River."
United States
Diane
RIVERKEEPER INN, Waterfront Property on the Potomac River

Cabin in Charles Town

10.0 out of 10, Exceptional, (9)
"Host communicated well. Great location right on the river. Family had a great time. "
United States
Geoff C.
The price is NZ$583
includes taxes & fees
1 Dec - 2 Dec
The River House

Cabin in Harpers Ferry

10.0 out of 10, Exceptional, (33)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
The price is NZ$669
includes taxes & fees
24 Nov - 25 Nov
Secluded Cabin a Stone's Throw From the A.T.!

Apartment in Martinsburg

9.8 out of 10, Exceptional, (20)
"Our family thoroughly our stay at this beautiful well-equipped house. Our family agreed this was our favorite vacation house. Great location on the Potomac River made better with all the available water toys. My Great-Grand Children enjoyed the fishing and even caught a few. We were slightly disappointed that the dock shown in one picture wasn't there. It was destroyed in a recent storm. "
United States
Anonymous traveller
Luxury Getaway on The Potomac

Chalet in Harpers Ferry

9.4 out of 10, Exceptional, (27)
"The house was very clean upon arrival. We enjoyed spending time in the hot tub and playing pool on a kid’s pool table. It was close the Harper’s Ferry. We also saw deer very close both days we were there, and we loved this!!"
United States
Kelly
The price is NZ$607
includes taxes & fees
1 Dec - 2 Dec
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Cabin in Keedysville

9.4 out of 10, Exceptional, (87)
"I loved the trip to that cabin, one of the most wonderful things"
United States
Roberto R.
The price is NZ$589
includes taxes & fees
24 Nov - 25 Nov
Antietam Creek - Quiet 2 Bedroom Cabin

Cabin in Harpers Ferry

9.2 out of 10, Wonderful, (62)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
The price is NZ$491
includes taxes & fees
2 Dec - 3 Dec
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
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

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$187 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?

Terra Alta - Incredible River Views and Hot Tub!: This holiday home rental outside of Middletown is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 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 private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 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.