Holiday Rentals in Middletown

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Our top choices for Middletown holiday rentals

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

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (111 reviews)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
The price is €166
includes taxes & fees
16 Feb - 17 Feb
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (142 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is €296
includes taxes & fees
13 Mar - 14 Mar
Charming "Cream of the Crop" Cape ~❤️of Middletown

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (71 reviews)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is €92
includes taxes & fees
23 Feb - 24 Feb
❤️ Secluded 1940s Romantic Tiny House on the River

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

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
10.0 out of 10, Exceptional, (9 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
The price is €140
includes taxes & fees
15 Feb - 16 Feb
Bring Your Own Boat - Meticulously restored house on the Potomac River

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Frederick
10.0 out of 10, Exceptional, (6 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is €181
includes taxes & fees
17 Feb - 18 Feb
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
9.4 out of 10, Exceptional, (11 reviews)
"Peaceful studio with a lovely view off the porch. Was easy to find and all aspects of the stay were smooth. Perfect place for a few days in Frederick "
United States
Morgan P.
The price is €147
includes taxes & fees
15 Feb - 16 Feb
Cozy Pine Tree Nest

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (62 reviews)
"We had a great time. House was very comfortable and location was perfect."
United States
Liz R.
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (8 reviews)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is €162
includes taxes & fees
17 Feb - 18 Feb
Pet-friendly, heart of downtown

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (28 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
Cozy, dog-friendly, downtown

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
Blue Ridge Summit
9.6 out of 10, Exceptional, (14 reviews)
"Great spot close to the wedding venue!!"
United States
Alfred T.
The price is €169
includes taxes & fees
17 Feb - 18 Feb
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
The price is €132
includes taxes & fees
16 Feb - 17 Feb
Birch Cabin at Hunting Creek Hideaway

Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (34 reviews)
"Mountain mama is organized and accessible throughout the stay. House was clean and comfortable with lively views. "
United States
Dennis W.
The price is €306
includes taxes & fees
16 Feb - 17 Feb
Antietam Look Out - Incredible Sunset Views!

Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (21 reviews)
"Great place for a family weekend retreat. "
United States
Dina S.
The price is €307
includes taxes & fees
16 Feb - 17 Feb
Peregrine's Perch - Cabin Overlooking the River!

Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (56 reviews)
"great communication, very easy people to talk to they were so sweet! the place was exactly what i was looking for and everything was kept very clean on arrival, and the area was lovely!"
United States
Maggie M.
The price is €155
includes taxes & fees
15 Feb - 16 Feb
Cozy Getaway near Harper`s Ferry, C&O & Potomac

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (24 reviews)
"Lovely views, very spacious, well appointed in terms of kitchen."
United States
sharyn m.
Art Docko - Lakefront Artist Retreat w/ Hot Tub!

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (121 reviews)
"Great location — right on the Carroll Creek Walk and a stone’s throw from excellent restaurants and nice shops. "
United States
Darby R.
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*
Downtown Frederick
9.0 out of 10, Wonderful, (77 reviews)
"Lovely place. It was perfect for our girls' trip long weekend. The rooms were so spacious and tastefully decorated. It was also super clean and had everything we needed, including for our night staying in with Door-dash to binge watch a couple Netflix series. The coffee lover in our group was so appreciative of the supplies and setup. The location is fabulous for walking the Creek Park, or to dinning and shopping options. We're looking forward to making this our Christmas present to each other...
United States
Lynne
The price is €222
includes taxes & fees
15 Feb - 16 Feb
*Luxury Condo In Downtown Frederick*

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
10.0 out of 10, Exceptional, (16 reviews)
"Great location. Great house. Could not have asked for more. "
United States
A. Bland and D. T.
The price is €327
includes taxes & fees
16 Feb - 17 Feb
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (7 reviews)
"Host was very responsive before and during my stay. Apartment is beautifully appointed and has all the amenities you need for a great weekend stay!!"
United States
lizbeth g.
Huge 1br apt, baby-friendly, dogs, walkable downtown

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

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Keedysville
9.8 out of 10, Exceptional, (67 reviews)
"Great stay! We would book again. "
United States
Sam F.
The price is €307
includes taxes & fees
16 Feb - 17 Feb
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
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, apart-hotels, 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 €92 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?

Charming "Cream of the Crop" Cape ~❤️of Middletown: This highly rated holiday home rental in Middletown offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Middletown?

Expedia has 6 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 Gambrill 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.