Holiday Rentals in Middletown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Middletown holiday rentals

A single-story house with a red front door, a small porch, and a mailbox.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (162 reviews)
"Great little spot!"
United States
Shelby W.
The price is €242
includes taxes & fees
15 Nov - 16 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

2. 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, (118 reviews)
"Beautiful property! Owner is very quick to communicate and did a fantastic job making it a very relaxing place to stay!"
United States
Cindy B.
The price is €196
includes taxes & fees
15 Nov - 16 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A log cabin interior with a wooden bench, a leather sofa, a coffee table, and a bookshelf.

3. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is €201
includes taxes & fees
25 Nov - 26 Nov
Cozy Downtown Cabin - Family Friendly
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
10.0 out of 10, Exceptional, (75 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is €236
includes taxes & fees
15 Nov - 16 Nov
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A kitchen with a dishwasher, a sink, and a stove. There are pots hanging above the sink and a window with a view of greenery outside.

5. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (72 reviews)
"The house is very cute and a perfect fit for our needs. We appreciated how clean the house was too! It's conveniently located to some many restaurants and shops. We would gladly stay here again!"
United States
Sara W.
The price is €255
includes taxes & fees
15 Nov - 16 Nov
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A compact kitchen with a coffee machine, microwave, and a small cart with kitchen tools.

6. 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, (18 reviews)
"Place was perfect and tbe location great. East in and out town..or to get to down town"
United States
Andrew
The price is €189
includes taxes & fees
22 Nov - 23 Nov
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

7. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (108 reviews)
"Great location"
United States
John
The price is €319
includes taxes & fees
15 Nov - 16 Nov
Modern Condo Right off Market Street
A hallway with brick walls, a white door, and a black console table with a vase.

8. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (102 reviews)
"Very convenient location with parking. Prompt communication with owner. However it needs a good deep clean. My towels were used and muddy like the workmen fixing the deck had just showered there. But I would stay there again if necessary."
United States
Jessica
The price is €304
includes taxes & fees
2 Dec - 3 Dec
Luxury Condo In Downtown Frederick
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

9. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (22 reviews)
"Our stay was so enjoyable!"
United States
Kimberly C.
The price is €386
includes taxes & fees
19 Nov - 20 Nov
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.2 out of 10, Wonderful, (149 reviews)
"Great location. Amenities were perfect for a little bit of an extended stay. Definitely will come back in the future"
United States
Dave T.
The price is €231
includes taxes & fees
15 Nov - 16 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A wooden deck leading to a cabin surrounded by dense forest.

11. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (101 reviews)
"The cabin was clean, spacious, and"
United States
Daniel
The price is €315
includes taxes & fees
15 Nov - 16 Nov
Antietam Creek - Quiet 2 Bedroom Cabin
A spacious living room with wooden walls and large windows, a fireplace, and a view of the outdoors.

12. 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, (78 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
The price is €429
includes taxes & fees
17 Nov - 18 Nov
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
An outdoor covered patio with wicker furniture and string lights, overlooking a forested area.

13. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (46 reviews)
"Beautiful house. Spent most of our time at the house sitting on the deck."
United States
Betty M.
The price is €409
includes taxes & fees
18 Nov - 19 Nov
Antietam Look Out - Incredible Sunset Views!
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

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

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
10.0 out of 10, Exceptional, (71 reviews)
"Cute downtown area with multiple spots to grab breakfast and convenience store stuff. Easy access to Harper's Ferry and made for a nice restful spot between hikes in nature and around town."
United States
Robert
The price is €157
includes taxes & fees
15 Nov - 16 Nov
Cozy Getaway near Harper`s Ferry, C&O & Potomac
A hammock hanging from a tree by a lake.

15. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is €96
includes taxes & fees
29 Nov - 30 Nov
❤️ Secluded 1940s Romantic Tiny House on the River
A two-story house with a porch decorated with string lights and garlands.

16. Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
9.8 out of 10, Exceptional, (13 reviews)
"We had a very comfortable stay. The apartment was clean, well-equipped, and had everything we needed. The instructions were clear, and the host was responsive and helpful throughout our stay. Parking was a little challenging, but aside from that, everything was great. We would happily stay here again!"
United States
Kamakshi B.
The price is €208
includes taxes & fees
14 Nov - 15 Nov
Historic Getaway near C&O Canal, hiking and biking
Living area

17. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (22 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
United States
Janice M.
The price is €432
includes taxes & fees
22 Nov - 23 Nov
Newly constructed 6 bedroom home
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

18. Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (29 reviews)
"really nice place"
United States
David R.
The price is €175
includes taxes & fees
15 Nov - 16 Nov
Beautiful, Historic, Hiking, Biking and C&O Canal
A backyard with a patio, outdoor seating, a fire pit, and a small shed.

19. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
Boonsboro
9.8 out of 10, Exceptional, (19 reviews)
"Cute place with a lot of character. Host was very responsive. We enjoyed our sray."
United States
Dawn V.
The price is €291
includes taxes & fees
15 Nov - 16 Nov
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A stone bridge with ivy over a calm waterway, surrounded by lush greenery and a clear sky.

20. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (13 reviews)
"We had a great time. It was perfect for us. I would highly recommend it to others and would not hesitate to return there when back in the area. "
United States
Tereasa G.
The price is €352
includes taxes & fees
15 Nov - 16 Nov
New townhouse
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.
View all properties

Find holiday rentals that suit your style

Apartment image
Apartments
Apartments
cabin image
Cabins
Cabins

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 €96 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?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This holiday home rental outside of Middletown is located in the mountains, and has a patio, a BBQ and air conditioning to put you at ease 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 7 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.