Middletown Vacation Rentals

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Our top choices for Middletown vacation rentals

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, (111 reviews)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
The price is CA $103
CA $263 total
includes taxes & fees
Feb 8 - Feb 9
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (142 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is CA $130
CA $337 total
includes taxes & fees
Feb 10 - Feb 11
Charming "Cream of the Crop" Cape ~❤️of Middletown

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (71 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 CA $54
CA $144 total
includes taxes & fees
Feb 16 - Feb 17
❤️ Secluded 1940s Romantic Tiny House on the River

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
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 CA $72
CA $250 total
includes taxes & fees
Feb 11 - Feb 12
Pet-friendly, heart of downtown

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (28 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
The price is CA $81
CA $262 total
includes taxes & fees
Feb 11 - Feb 12
Cozy, dog-friendly, downtown

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, (6 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is CA $72
CA $268 total
includes taxes & fees
Feb 9 - Feb 10
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
The price is CA $133
CA $207 total
includes taxes & fees
Feb 9 - Feb 10
Birch Cabin at Hunting Creek Hideaway

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 CA $103
CA $220 total
includes taxes & fees
Mar 8 - Mar 9
Bring Your Own Boat - Meticulously restored house on the Potomac River

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

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (7 reviews)
"The appartment was lovely and the location was great. The parking was a struggle, but all city locations are. I would definitely recommend staying here."
United States
Ashley B.
The price is CA $118
CA $307 total
includes taxes & fees
Mar 4 - Mar 5
Huge 1br apt, baby-friendly, dogs, walkable downtown

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, (54 reviews)
"great communication, very easy people to talk to they were so sweet! the place was exactly what i was looking for and everything was kept very clean on arrival, and the area was lovely!"
United States
Maggie M.
The price is CA $123
CA $232 total
includes taxes & fees
Feb 25 - Feb 26
Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
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 CA $110
CA $233 total
includes taxes & fees
Feb 8 - Feb 9
Cozy Pine Tree Nest

Aslan's How - Cabin with Valley Views & Hot Tub!

Aslan's How - Cabin with Valley Views & Hot Tub!
Harpers Ferry
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 CA $137
CA $520 total
includes taxes & fees
Feb 8 - Feb 9
Aslan's How - Cabin with Valley Views & Hot Tub!

Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (34 reviews)
"Mountain mama is organized and accessible throughout the stay. House was clean and comfortable with lively views. "
United States
Dennis W.
The price is CA $137
CA $485 total
includes taxes & fees
Feb 12 - Feb 13
Antietam Look Out - Incredible Sunset Views!

~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, (84 reviews)
"The Host were excellent, the amenities were superb and exactly as described. Beautiful view and a great place to just get away!"
United States
Mendy I.
The price is CA $179
CA $434 total
includes taxes & fees
Feb 9 - Feb 10
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (62 reviews)
"We had a great time. House was very comfortable and location was perfect."
United States
Liz R.
The price is CA $159
CA $358 total
includes taxes & fees
Feb 8 - Feb 9
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
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 CA $137
CA $539 total
includes taxes & fees
Feb 8 - Feb 9
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
United States
Vinod B.
The price is CA $108
CA $415 total
includes taxes & fees
Feb 10 - Feb 11
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!
Sharpsburg
10.0 out of 10, Exceptional, (42 reviews)
"We had an amazing time - lots of walks and places to see - very historical - winery right next door which was an added bonus - accommodation was everything we needed and more - look out for a friendly cat that paid a few visits - thank you Jordan for a great time and will definitely come back to the area"
United Kingdom
Jo W.
The price is CA $103
CA $348 total
includes taxes & fees
Feb 19 - Feb 20
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

*Modern Condo In Downtown Frederick*

*Modern Condo In Downtown Frederick*
Downtown Frederick
9.2 out of 10, Wonderful, (78 reviews)
"Great location and has exactly what you need to enjoy a stay in downtown Frederick!"
United States
Amy R.
The price is CA $144
CA $365 total
includes taxes & fees
Feb 8 - Feb 9
*Modern Condo In Downtown Frederick*

Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (21 reviews)
"Great place for a family weekend retreat. "
United States
Dina S.
The price is CA $137
CA $494 total
includes taxes & fees
Feb 8 - Feb 9
Peregrine's Perch - Cabin Overlooking the River!
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

Find out more about Middletown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

NEW! Ferrystone Lodge: Mountain Retreat w/ Patio & Fireplace: This vacation home rental near Middletown offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 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.