A stone tower with a staircase leading up to it.

Middletown Vacation Rentals

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Check prices for these dates

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

Our top choices for Middletown vacation 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, (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 ￥15,801
￥36,178 total
includes taxes & fees
Nov 15 - Nov 16
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, (162 reviews)
"Great little spot!"
United States
Shelby W.
The price is ￥19,751
￥46,227 total
includes taxes & fees
Nov 16 - Nov 17
Charming "Cream of the Crop" Cape ~❤️of Middletown
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 ￥30,022
￥34,503 total
includes taxes & fees
Nov 25 - Nov 26
Cozy Downtown Cabin - Family Friendly
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

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 ￥13,471
￥37,966 total
includes taxes & fees
Nov 11 - Nov 12
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A compact kitchen with a coffee machine, microwave, and a small cart with kitchen tools.

5. 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 ￥12,691
￥34,556 total
includes taxes & fees
Nov 22 - Nov 23
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

6. ❤️ 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 ￥6,989
￥16,057 total
includes taxes & fees
Nov 16 - Nov 17
❤️ Secluded 1940s Romantic Tiny House on the River
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

7. 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, (148 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 ￥15,801
￥39,695 total
includes taxes & fees
Nov 15 - Nov 16
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

8. 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 ￥15,643
￥26,966 total
includes taxes & fees
Dec 8 - Dec 9
Cozy Getaway near Harper`s Ferry, C&O & Potomac
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.

9. 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 ￥22,721
￥44,243 total
includes taxes & fees
Nov 11 - Nov 12
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

10. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (46 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 ￥16,323
￥62,057 total
includes taxes & fees
Nov 18 - Nov 19
Antietam Look Out - Incredible Sunset Views!
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

11. 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 ￥18,250
￥29,897 total
includes taxes & fees
Dec 9 - Dec 10
Beautiful, Historic, Hiking, Biking and C&O Canal
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

12. 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 ￥29,810
￥55,118 total
includes taxes & fees
Nov 11 - Nov 12
Modern Condo Right off Market Street
A modern kitchen with grey cabinets, a central island, and pendant lighting.

13. 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 ￥24,390
￥49,371 total
includes taxes & fees
Dec 1 - Dec 2
Luxury Condo In Downtown Frederick
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

14. 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 ￥18,645
￥68,533 total
includes taxes & fees
Nov 12 - Nov 13
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A two-story house with a porch decorated with string lights and garlands.

15. 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 ￥20,857
￥37,350 total
includes taxes & fees
Nov 16 - Nov 17
Historic Getaway near C&O Canal, hiking and biking
A cozy room with a bed, a sofa, a wooden dresser, a desk with a lamp, and a kitchen area with wooden cabinets and a microwave.

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

Loft Apt Just off C&O near Harpers Ferry and AT
Brunswick
10.0 out of 10, Exceptional, (23 reviews)
"The place was nice and cozy"
United States
Andrew E.
The price is ￥17,084
￥30,373 total
includes taxes & fees
Nov 15 - Nov 16
Loft Apt Just off C&O near Harpers Ferry and AT
A living room with a dining table, chairs, a sofa, and a television.

17. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
The price is ￥19,018
￥33,414 total
includes taxes & fees
Nov 15 - Nov 16
Quaint Mini Cottage in Shepherdstown - Walking Distance
A wooden cabin with a patio area, outdoor seating, and a fire pit.

18. 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 ￥23,645
￥49,922 total
includes taxes & fees
Dec 10 - Dec 11
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

19. 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 ￥43,582
￥68,371 total
includes taxes & fees
Nov 16 - Nov 17
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

20. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (57 reviews)
"Very comfortable and cozy. Our family had a great stay here."
United States
bethany c.
The price is ￥23,376
￥42,349 total
includes taxes & fees
Nov 12 - Nov 13
Charming Cabin in the Woods with River Access
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, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

10/10 Excellent
"Staff was incredibly friendly and the hotel was small and was very quiet throughout the night."
David 1-night trip
Posted 4 hours ago
Country Inn & Suites by Radisson, Frederick, MD

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
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  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, we offer vacation rentals near well known points of interest in Middletown, or you can select a secluded option if you're looking for relaxation. 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's the top vacation rental in Middletown?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This vacation home rental near Middletown is located in the mountains and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Middletown?

Expedia has 7 vacation 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 vacation rentals like in Middletown?

Vacation rentals are private accommodations you can book for a couple days or more in Middletown. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a small group gathering.