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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Middletown vacation rentals

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

Cabin in Middletown

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
9.6 out of 10, Exceptional, (111 reviews)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
The price is ￥10,263
￥28,619 total
includes taxes & fees
Jan 13 - Jan 14
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Exterior
Charming "Cream of the Crop" Cape ~❤️of Middletown

Vacation Home in Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (141 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is ￥24,473
￥50,544 total
includes taxes & fees
Jan 18 - Jan 19
Charming "Cream of the Crop" Cape ~❤️of Middletown
Exterior
❤️ Secluded 1940s Romantic Tiny House on the River

Cabin in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
9.8 out of 10, Exceptional, (70 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 ￥6,252
￥16,540 total
includes taxes & fees
Jan 19 - Jan 20
❤️ Secluded 1940s Romantic Tiny House on the River
Smart TV
Pet-friendly, heart of downtown

Apartment in Frederick

Pet-friendly, heart of downtown
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 ￥8,810
￥29,925 total
includes taxes & fees
Jan 19 - Jan 20
Pet-friendly, heart of downtown
1 bedroom, free WiFi, bed sheets
Cozy, dog-friendly, downtown

Apartment in Frederick

Cozy, dog-friendly, downtown
10.0 out of 10, Exceptional, (26 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
The price is ￥9,379
￥30,025 total
includes taxes & fees
Jan 14 - Jan 15
Cozy, dog-friendly, downtown
Interior
Bring Your Own Boat - Meticulously restored house on the Potomac River

Cottage in Hedgesville

Bring Your Own Boat - Meticulously restored house on the Potomac River
10.0 out of 10, Exceptional, (9 reviews)
"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 ￥11,842
￥25,452 total
includes taxes & fees
Jan 13 - Jan 14
Bring Your Own Boat - Meticulously restored house on the Potomac River
TV, foosball, books
Cozy Pine Tree Nest

Apartment in Frederick

Cozy Pine Tree Nest
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 ￥12,647
￥26,796 total
includes taxes & fees
Jan 13 - Jan 14
Cozy Pine Tree Nest
Fridge, microwave, coffee/tea maker, toaster
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Apartment in Frederick

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
10.0 out of 10, Exceptional, (6 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is ￥8,270
￥30,523 total
includes taxes & fees
Jan 13 - Jan 14
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Dining
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

Cabin in Harpers Ferry

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
10.0 out of 10, Exceptional, (83 reviews)
"This is a super cute mountain cabin that has been completely redone with some pretty high end finishes. Our family thoroughly enjoyed our quick visit!"
United States
Sara S.
The price is ￥15,631
￥43,236 total
includes taxes & fees
Jan 13 - Jan 14
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
TV, fireplace
Aslan's How - Cabin with Valley Views & Hot Tub!

Cabin in Harpers Ferry

Aslan's How - Cabin with Valley Views & Hot Tub!
2.0 star property
9.8 out of 10, Exceptional, (8 reviews)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
The price is ￥15,789
￥59,578 total
includes taxes & fees
Jan 13 - Jan 14
Aslan's How - Cabin with Valley Views & Hot Tub!
Interior
New, Contemporary House in Historic Harpers Ferry

Vacation Home in Harpers Ferry

New, Contemporary House in Historic Harpers Ferry
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The home was perfect for our visit.We were in and out all weekend but really appreciated the well stocked kitchen supplies, the comfortable beds and the hot water levels. We were able to relax in the spacious living room and spend some time on the little outdoor areas. We would stay again but if the group was much bigger there may be issues as there are only bathrooms on the first floor. "
United States
Erin J.
The price is ￥15,789
￥57,534 total
includes taxes & fees
Jan 15 - Jan 16
New, Contemporary House in Historic Harpers Ferry
Dining
Log Cabin w/ Hot Tub & Waterfront Patio!

Cabin in Harpers Ferry

Log Cabin w/ Hot Tub & Waterfront Patio!
2.0 star property
9.8 out of 10, Exceptional, (14 reviews)
"Everything was great! We had a lovely stay."
United States
Beth D.
The price is ￥15,789
￥55,539 total
includes taxes & fees
Jan 19 - Jan 20
Log Cabin w/ Hot Tub & Waterfront Patio!
Smart TV
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Cabin in Harpers Ferry

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
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 ￥15,789
￥59,338 total
includes taxes & fees
Jan 15 - Jan 16
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
1 bedroom, WiFi, bed sheets
The Carriage House at Carrot Top Cottage

Cottage in Harpers Ferry

The Carriage House at Carrot Top Cottage
9.8 out of 10, Exceptional, (43 reviews)
"The place was super cute and clean. It was the perfect little getaway spot for my husband and I’s anniversary. "
United States
Holly W.
The price is ￥15,473
￥26,898 total
includes taxes & fees
Jan 13 - Jan 14
The Carriage House at Carrot Top Cottage
Exterior detail
Cozy Getaway near Harper`s Ferry, C&O & Potomac

Apartment in Brunswick

Cozy Getaway near Harper`s Ferry, C&O & Potomac
9.8 out of 10, Exceptional, (54 reviews)
"Great little apartment, great value, walking distance to trail and right in town!"
United States
Jess A.
The price is ￥14,210
￥26,778 total
includes taxes & fees
Jan 13 - Jan 14
Cozy Getaway near Harper`s Ferry, C&O & Potomac
Property grounds
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Cabin in Waynesboro

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
9.8 out of 10, Exceptional, (92 reviews)
"The Toll House was clean, had all the amenities advertised, and host had great communication. Very nice to have a fenced yard for my small dog to roam. I recommend this to others! "
United States
Sharon
The price is ￥14,210
￥34,894 total
includes taxes & fees
Jan 13 - Jan 14
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Fridge, microwave, oven, stovetop
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Vacation Home in Jefferson

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
9.8 out of 10, Exceptional, (58 reviews)
"Great house to use during our visit to Jefferson. Kitchen is well equipped, and coffee supplies are provided. Comfy beds plus air conditioning made for great sleep. "
United States
Kathryn B.
The price is ￥19,736
￥44,853 total
includes taxes & fees
Jan 17 - Jan 18
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Dining
*Luxury Condo In Downtown Frederick*

Vacation Home in Downtown Frederick

*Luxury Condo In Downtown Frederick*
9.0 out of 10, Wonderful, (72 reviews)
"Very nice inside, clean, everything worked, chairs and beds were comfortable. Very nice stay.The backyard where we parked is a bit rough looking, and we're glad it didn't rain as walking from the car to the house is over rather thin grass/dirt. I pulled the car around to the front the night we got dressed up and went out. "
United States
Ray S.
The price is ￥16,105
￥41,506 total
includes taxes & fees
Jan 13 - Jan 14
*Luxury Condo In Downtown Frederick*
Property grounds
Birch Cabin at Hunting Creek Hideaway

Cabin in Thurmont

Birch Cabin at Hunting Creek Hideaway
9.8 out of 10, Exceptional, (19 reviews)
"It was a fabulous stay, and Brittany, the host, was very helpful with bringing a gas grill, AC, and communication. The scenery is very beautiful and it's very quiet. Great place for a hiking getaway."
United States
Fr. Andrew H.
The price is ￥15,489
￥23,950 total
includes taxes & fees
Jan 19 - Jan 20
Birch Cabin at Hunting Creek Hideaway
Terrace/patio
Rebels Rest - Cabin with Enchanting Sunset Views!

Cabin in Harpers Ferry

Rebels Rest - Cabin with Enchanting Sunset Views!
9.8 out of 10, Exceptional, (31 reviews)
"Beautiful Sunsets, older cabin, not too steep of a drive up, outside deck is nice and fire pit area out front! Harper’s Ferry Area is cute and full of history! Be in shape to hike and climb while you are here, especially if you plan on doing a ghost walk after walking the town all day! 5 friends girls trip was great! "
United States
Teresa R.
Rebels Rest - Cabin with Enchanting Sunset Views!
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
"The room was clean, with nice amenities and a comfortable bed. The bathroom was clean and the water pressure was great. There was a good selection of channels on the television and the staff were very pleasant and efficient. I left too early each day to try the breakfast, but it smelled pretty good and the dining room was large with plenty of tables. There was a nice well lit grass area out front to walk the dog. My only complaints were that the closet, fridge and microwave were tricky to access and the room, while large, seemed a little cramped and oddly laid out. I only managed to connect to the wi-fi once and it was very slow."
Samantha 2-night trip
Posted 11 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
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • 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?

1805 Farmhouse with Heated Pool in Harpers Ferry: This vacation home rental near Middletown is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family. It offers a furnished patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Middletown?

Expedia has 5 vacation 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 Washington Monument State Park.

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.