Middletown Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Middletown vacation rentals

Interior

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, (114 reviews)
"Good stay. Would visit again. "
United States
Lonnie F.
The price is ￥13,563
￥33,490 total
includes taxes & fees
May 4 - May 5
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (145 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is ￥11,968
￥35,521 total
includes taxes & fees
Apr 30 - May 1
Charming "Cream of the Crop" Cape ~❤️of Middletown
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (74 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is ￥11,968
￥23,042 total
includes taxes & fees
May 20 - May 21
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
9.8 out of 10, Exceptional, (27 reviews)
"We had a very nice stay here, kitchen and bathroom had all necessary amenities provided. Cozy cabin, a little chilly at night but blankets were provided as well so it was OK."
United States
Emily Z.
The price is ￥14,792
￥23,291 total
includes taxes & fees
May 13 - May 14
Birch Cabin at Hunting Creek Hideaway
Interior

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 ￥11,968
￥25,723 total
includes taxes & fees
Apr 30 - May 1
Bring Your Own Boat - Meticulously restored house on the Potomac River
Fridge, microwave, coffee/tea maker, toaster

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, (9 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is ￥9,751
￥33,002 total
includes taxes & fees
May 3 - May 4
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Dining

Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!
Harpers Ferry
9.6 out of 10, Exceptional, (20 reviews)
"House was very clean and the hosts were responsive and very nice! Great place for a quiet weekend getaway. "
United States
Nicole H.
The price is ￥15,957
￥56,309 total
includes taxes & fees
May 4 - May 5
Log Cabin w/ Hot Tub & Waterfront Patio!
Property grounds

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Waynesboro
9.8 out of 10, Exceptional, (100 reviews)
"Beautiful location! The host was extremely responsive with any questions most texts were returned within minutes! Will definitely stay here again. "
United States
Michael R.
The price is ￥16,595
￥38,928 total
includes taxes & fees
Apr 30 - May 1
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Outdoor spa tub

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (21 reviews)
"Great view, very secluded"
United States
Matt s.
The price is ￥15,941
￥59,485 total
includes taxes & fees
May 11 - May 12
Cottage w/ Hot Tub and 100-Mile Valley Views!
Smart TV

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (8 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
The price is ￥10,915
￥31,867 total
includes taxes & fees
May 5 - May 6
Pet-friendly, heart of downtown
Smart TV, fireplace

Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (22 reviews)
"Great place for a family weekend retreat. "
United States
Dina S.
The price is ￥15,941
￥57,493 total
includes taxes & fees
May 4 - May 5
Peregrine's Perch - Cabin Overlooking the River!
Terrace/patio

Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (34 reviews)
"Would come back anytime, very scenic and easy check-in process"
United States
Mark F.
The price is ￥15,957
￥58,023 total
includes taxes & fees
May 6 - May 7
Rebels Rest - Cabin with Enchanting Sunset Views!
Exterior

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (22 reviews)
"The house had wonderful spaces to use for our weekend getaway!"
United States
Jessame P.
The price is ￥15,941
￥58,000 total
includes taxes & fees
May 7 - May 8
Lake View Retreat - Cottage Near a Peaceful Lake!
Dining

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Harpers Ferry
10.0 out of 10, Exceptional, (88 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
The price is ￥25,276
￥54,650 total
includes taxes & fees
Apr 30 - May 1
Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Dining

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Harpers Ferry
9.6 out of 10, Exceptional, (45 reviews)
"The house was great, clean, beautiful setting."
United States
Brandon M.
The price is ￥15,941
￥56,760 total
includes taxes & fees
May 7 - May 8
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Interior

Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
The price is ￥15,957
￥54,014 total
includes taxes & fees
Apr 30 - May 1
Cabin at the Gap | You Won't Believe the View!
Interior

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
The price is ￥31,882
￥52,382 total
includes taxes & fees
May 11 - May 12
Antietam Creek - Quiet 2 Bedroom Cabin
Outdoor dining

Woodland cabin w/hot tub & game room

Woodland cabin w/hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (65 reviews)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
The price is ￥26,270
￥51,367 total
includes taxes & fees
May 4 - May 5
Woodland cabin w/hot tub & game room
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (68 reviews)
"Great kitchen, very comfortable beds. Well air conditioned."
United States
Whitney C.
The price is ￥18,526
￥41,289 total
includes taxes & fees
May 4 - May 5
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Smart TV, fireplace

Secluded Cabin a Stone's Throw From the A.T.!

Secluded Cabin a Stone's Throw From the A.T.!
Harpers Ferry
10.0 out of 10, Exceptional, (36 reviews)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
The price is ￥15,957
￥59,979 total
includes taxes & fees
Apr 30 - May 1
Secluded Cabin a Stone's Throw From the A.T.!
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

Hampton Inn & Suites Frederick-Fort Detrick

Hampton Inn & Suites Frederick-Fort Detrick

10/10 Excellent
"bed was very comfortable"
john 1-night trip
Posted 9 hours ago
Hampton Inn & Suites Frederick-Fort Detrick

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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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?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This vacation home rental near Middletown offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Middletown?

Expedia has 6 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.