A stone tower with a staircase leading up to it.

Middletown Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Middletown holiday rentals

A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

1. 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, (117 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 AU$306
includes taxes & fees
26 Oct - 27 Oct
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (160 reviews)
"Great little spot!"
United States
Shelby W.
The price is AU$446
includes taxes & fees
3 Nov - 4 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown
A bedroom with a wooden bed, a dresser, a mirror, and a painting on the wall.

3. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is AU$361
includes taxes & fees
26 Oct - 27 Oct
Cozy Downtown Cabin - Family Friendly
A bedroom with a bed, a bedside table with a lamp, a window with a view, and a decorative wall piece.

4. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean place. "
United States
Warren B.
The price is AU$320
includes taxes & fees
28 Oct - 29 Oct
Cozy, dog-friendly, downtown
A storefront with a large glass window, a wooden door, and a brick sidewalk.

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

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (14 reviews)
"Great location for a peaceful solo night away -- thanks!"
United States
Kristina S.
Huge 1br apt, baby-friendly, dogs, walkable downtown
A modern apartment with a living room, kitchen, and dining area.

6. Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (9 reviews)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is AU$320
includes taxes & fees
28 Oct - 29 Oct
Pet-friendly, heart of downtown
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

7. ❤️ 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 AU$155
includes taxes & fees
1 Nov - 2 Nov
❤️ Secluded 1940s Romantic Tiny House on the River
A patio area with a wooden table, chairs, a decorative vase, and a fire pit.

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

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
10.0 out of 10, Exceptional, (54 reviews)
"Great lodging and communicative host"
United States
Peggy D.
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

9. 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, (74 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is AU$366
includes taxes & fees
26 Oct - 27 Oct
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

10. 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, (70 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 AU$260
includes taxes & fees
1 Nov - 2 Nov
Cozy Getaway near Harper`s Ferry, C&O & Potomac
A living room with a large mirror, a sofa, a television, and decorative items.

11. Downtown Frederick retreat with parking. Dog- and baby-friendly!

Downtown Frederick retreat with parking. Dog- and baby-friendly!
Frederick
9.8 out of 10, Exceptional, (8 reviews)
"This place looked exactly like the photos, very clean, super organized, and well designed. We were very comfortable during our stay and would stay here again."
United States
Dvorak A.
The price is AU$402
includes taxes & fees
25 Oct - 26 Oct
Downtown Frederick retreat with parking. Dog- and baby-friendly!
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

12. 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 AU$288
includes taxes & fees
1 Nov - 2 Nov
Beautiful, Historic, Hiking, Biking and C&O Canal
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

13. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (45 reviews)
"The house was as great! Plenty of space for 5 adults. Conveniently located to the areas we wanted to visit. Very quiet location"
United States
Melisa T.
The price is AU$570
includes taxes & fees
4 Nov - 5 Nov
Antietam Look Out - Incredible Sunset Views!
A living room with a dining table, chairs, a sofa, and a television.

14. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
The price is AU$321
includes taxes & fees
26 Oct - 27 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

15. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (106 reviews)
"Great place!"
United States
Danielle G.
The price is AU$498
includes taxes & fees
3 Nov - 4 Nov
Modern Condo Right off Market Street
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.

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

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (71 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 AU$362
includes taxes & fees
26 Oct - 27 Oct
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

17. 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, (76 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 AU$603
includes taxes & fees
3 Nov - 4 Nov
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

18. 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, (146 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is AU$439
includes taxes & fees
1 Nov - 2 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A modern kitchen with grey cabinets, a central island, and pendant lighting.

19. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (99 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 AU$491
includes taxes & fees
27 Oct - 28 Oct
Luxury Condo In Downtown Frederick
A two-story house with a porch decorated with string lights and garlands.

20. 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)
"Very friendly host who made communications easy. We left our iPad behind and they called us right away. The apartment was large, beds were comfortable, and the bathroom renovation was beautiful with a great shower. It is about a block from the C&O trail plus free parking on the property."
United States
Kelly
The price is AU$357
includes taxes & fees
1 Nov - 2 Nov
Historic Getaway near C&O Canal, hiking and biking
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

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

10/10 Excellent
"Comfortable and clean room in a convenient location. The room was large, quiet and had nice amenities and convenient outlets."
Paula 1-night trip
Posted 19 hours ago
Country Inn & Suites by Radisson, Hagerstown, MD

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$155 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?

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.