Middletown Holiday Rentals

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Holiday Rentals in Middletown

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

Middletown
9.6 out of 10, Exceptional, (110)
"Beautiful cabin with an adorable mini oven, great TV, creature comforts of robes and throws. Best sleep I’ve ever had in the quiet."
United States
Sharon H.
The price is AU$305
includes taxes & fees
30 Nov - 1 Dec
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Charming "Cream of the Crop" Cape ~❤️of Middletown

Middletown
10.0 out of 10, Exceptional, (139)
"Love the place will book again"
United States
WAYNE M.
The price is AU$389
includes taxes & fees
30 Nov - 1 Dec
Charming "Cream of the Crop" Cape ~❤️of Middletown

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is AU$163
includes taxes & fees
9 Dec - 10 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

Bring Your Own Boat - Meticulously restored house on the Potomac River

Hedgesville
10.0 out of 10, Exceptional, (9)
"Cute little house that my husband and I enjoyed for the weekend. Great location close to Martinsburg. It had everything we needed for our weekend The host communicated well, we had no issues, and we would definitely stay here again. Thank you!"
United States
Jennifer E.
The price is AU$249
includes taxes & fees
30 Nov - 1 Dec
Bring Your Own Boat - Meticulously restored house on the Potomac River

Pet-friendly, heart of downtown

Frederick
10.0 out of 10, Exceptional, (6)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is AU$305
includes taxes & fees
11 Dec - 12 Dec
Pet-friendly, heart of downtown

Cozy, dog-friendly, downtown

Frederick
10.0 out of 10, Exceptional, (26)
"Super cute and was the PERFECT location! We had a great stay! "
United States
Sarah S.
The price is AU$305
includes taxes & fees
11 Dec - 12 Dec
Cozy, dog-friendly, downtown

Charming in-law suite. The open-concept living area welcomes you.

Blue Ridge Summit
9.4 out of 10, Exceptional, (11)
"Very restful very accommodating and very helpful ownerd"
United States
Donna B.
The price is AU$295
includes taxes & fees
30 Nov - 1 Dec
Charming in-law suite. The open-concept living area welcomes you.

Birch Cabin at Hunting Creek Hideaway

Thurmont
9.8 out of 10, Exceptional, (18)
"Was wonderful..private and peaceful. Perfect getaway. "
United States
Courtney G.
The price is AU$215
includes taxes & fees
2 Dec - 3 Dec
Birch Cabin at Hunting Creek Hideaway

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Frederick
10.0 out of 10, Exceptional, (62)
"We thoroughly enjoyed our stay in Frederick. The cottage was comfortable and an easy walk to shops, parks and restaurants. We would definitely stay here for our next trip to Frederick. "
United States
Karen B.
The price is AU$399
includes taxes & fees
2 Dec - 3 Dec
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Aslan's How - Cabin with Valley Views & Hot Tub!

2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (8)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
The price is AU$582
includes taxes & fees
30 Nov - 1 Dec
Aslan's How - Cabin with Valley Views & Hot Tub!

Cozy Pine Tree Nest

Frederick
9.4 out of 10, Exceptional, (11)
"Really nice apartment was just what we wanted for a weekend while here to run the JFK 50 miler"
United States
David S.
The price is AU$262
includes taxes & fees
11 Dec - 12 Dec
Cozy Pine Tree Nest

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Waynesboro
9.8 out of 10, Exceptional, (89)
"Love it been coming here for a few years now "
United States
Kristina M.
The price is AU$347
includes taxes & fees
30 Nov - 1 Dec
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Log Cabin w/ Hot Tub & Waterfront Patio!

2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (11)
"Everything was great! We had a lovely stay."
United States
Beth D.
The price is AU$511
includes taxes & fees
1 Dec - 2 Dec
Log Cabin w/ Hot Tub & Waterfront Patio!

6 Mi to Gambrill State Park: Family Gem w/ Patio!

3.0 star property
Frederick
The price is AU$1,341
includes taxes & fees
23 Dec - 24 Dec
6 Mi to Gambrill State Park: Family Gem w/ Patio!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Keedysville
9.8 out of 10, Exceptional, (64)
"Very nice property. My family had a fun stay!"
United States
Radha V.
The price is AU$568
includes taxes & fees
4 Dec - 5 Dec
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Antietam Look Out - Incredible Sunset Views!

Keedysville
9.8 out of 10, Exceptional, (33)
"The property was perfect for our family. It was well equipped with all the kitchen necessities. plenty of space, bedrooms, and bathrooms to accommodate 7 adults and a 1 yr old. Great location for seeing sites. "
United States
Barbara B.
The price is AU$553
includes taxes & fees
3 Dec - 4 Dec
Antietam Look Out - Incredible Sunset Views!

Loft Apt Just off C&O near Harpers Ferry and AT

Brunswick
10.0 out of 10, Exceptional, (16)
"Everything was great. Would stay again! Accurate listing."
United States
Marlin S.
The price is AU$285
includes taxes & fees
28 Dec - 29 Dec
Loft Apt Just off C&O near Harpers Ferry and AT

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Jefferson
9.8 out of 10, Exceptional, (58)
"We loved visiting! Wish we could've stayed longer. The accommodations were great; super comfortable and inviting. Everyone enjoyed themselves. Thanks for having us!"
United States
David F.
The price is AU$389
includes taxes & fees
30 Nov - 1 Dec
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Harpers Ferry
10.0 out of 10, Exceptional, (5)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
United States
Vinod B.
The price is AU$599
includes taxes & fees
1 Dec - 2 Dec
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Frederick
10.0 out of 10, Exceptional, (34)
"Two bedroom each with its own bathroom was so nice for our small group. The apartment is walking distance to town and in a quiet neighborhood. Our stay was perfect!"
United States
Jennifer S.
The price is AU$387
includes taxes & fees
30 Nov - 1 Dec
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
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 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?

Riverside cottage, minutes from historic Harpers Ferry! Private river access!: This holiday home rental outside of Middletown offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable 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.

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 John Brown Wax Museum, 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.