A stone tower with a staircase leading up to it.

Middletown Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Middletown vacation rentals

Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (149 reviews)
"An absolutely charming getaway spot tucked in a small town with trendy shops and eateries. Our host gave fabulous recommendations and the property was spotless, cozy and well equipped for the perfect weekend getaway."
United States
Jennifer P.
The price is AED 606
AED 1,246 total
includes taxes & fees
26 Jul - 27 Jul
Charming "Cream of the Crop" Cape ~❤️of Middletown
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, (116 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 AED 533
AED 1,016 total
includes taxes & fees
5 Aug - 6 Aug
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
House (3 Bedrooms) | Interior

Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is AED 599
AED 1,587 total
includes taxes & fees
12 Jul - 13 Jul
Rural & Historic Detour Escape w/ Horses On-site!
Interior

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Fairfield
9.8 out of 10, Exceptional, (51 reviews)
"Everything was great!"
United States
Corey G.
The price is AED 1,469
AED 2,307 total
includes taxes & fees
12 Jul - 13 Jul
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Interior

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Sharpsburg
8.4 out of 10, Very Good, (63 reviews)
"Great location, spacious living area, plenty of linens, and excellent fire pit! "
United States
Maria Elena S.
The price is AED 658
AED 1,577 total
includes taxes & fees
12 Jul - 13 Jul
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Exterior

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.8 out of 10, Exceptional, (205 reviews)
"This was an amazing experience to stay in a house that was here during the battle, look forward to may more visits while I see the place I love. "
United States
Dave W.
The price is AED 533
AED 646 total
includes taxes & fees
12 Jul - 13 Jul
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (79 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is AED 248
AED 500 total
includes taxes & fees
22 Jul - 23 Jul
❤️ Secluded 1940s Romantic Tiny House on the River
Fridge, microwave, oven, stovetop

Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (19 reviews)
"Everything was excellent "
United States
Ronald G.
The price is AED 801
AED 1,748 total
includes taxes & fees
22 Jul - 23 Jul
Newly constructed 6 bedroom home
Outdoor dining

Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge

Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
Shannondale
10.0 out of 10, Exceptional, (4 reviews)
"My family and ai had an amazing stay at Deb and Alex’s rental in WV! It was easy to check-in, very clean, and had convenient amenities! Would definitely consider staying with them again!"
United States
Anonymous traveler
The price is AED 1,164
AED 2,164 total
includes taxes & fees
3 Aug - 4 Aug
Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
Dining

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (19 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
The price is AED 1,525
AED 2,492 total
includes taxes & fees
28 Jul - 29 Jul
Exclusive Wooded Chalet w Magnificent River Views
Exterior

New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (11 reviews)
"We had a great time. It was perfect for us. I would highly recommend it to others and would not hesitate to return there when back in the area. "
United States
Tereasa G.
The price is AED 625
AED 1,515 total
includes taxes & fees
10 Jul - 11 Jul
New townhouse
Exterior detail

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
Blue Ridge Summit
9.6 out of 10, Exceptional, (17 reviews)
"Location and amenities"
United States
Shane B.
The price is AED 262
AED 678 total
includes taxes & fees
15 Jul - 16 Jul
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
House (3 Bedrooms) | Interior

5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden

5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden
3.0 star property
Harpers Ferry
The price is AED 621
AED 1,372 total
includes taxes & fees
1 Aug - 2 Aug
5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden
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)
"Everything was very clean and comfortable. The kitchen was well equipped."
United States
Linda D.
The price is AED 463
AED 1,004 total
includes taxes & fees
21 Jul - 22 Jul
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Terrace/patio

Cozy Bear-Themed Mountain Cabin in Harpers Ferry with Relaxing Jacuzzi Hot Tub

Cozy Bear-Themed Mountain Cabin in Harpers Ferry with Relaxing Jacuzzi Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (62 reviews)
"The hosts were very friendly and the house was just as expected. Our family of 4 and furry friend ba sa great time! "
United States
Tyler W.
Cozy Bear-Themed Mountain Cabin in Harpers Ferry with Relaxing Jacuzzi Hot Tub
Interior

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
10.0 out of 10, Exceptional, (22 reviews)
"GREAT stay…loved the location, the hot tub, the amenities, and the host."
United States
Domenic E.
The price is AED 826
AED 1,453 total
includes taxes & fees
21 Jul - 22 Jul
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Interior

Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping

Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping
Leesburg
8.8 out of 10, Excellent, (11 reviews)
"What an excellent stay! Ayda was an amazing host. The dome is very private and wonderfully outfitted. The hot tub was awesome and everything was clean and so comfy. In summer I can only imagine it is even more secluded as the trees leaf out!! Highly recommended and planning another stay. "
United States
Carter S.
The price is AED 613
AED 1,097 total
includes taxes & fees
21 Jul - 22 Jul
Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping
Outdoor dining

3BR cabin w/ hot tub & game room

3BR cabin w/ hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (65 reviews)
"While there was something left to be desired by the kitchen utensils and cookware, this place is located off the beaten path in a beautiful mountainside area. Definitely worth the price. Just bring your own pot holders and pizza cutter if you plan on having pizza lol. "
United States
Tyrell O.
The price is AED 748
AED 1,372 total
includes taxes & fees
12 Jul - 13 Jul
3BR cabin w/ hot tub & game room
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (95 reviews)
"Excellent location and clean, spacious townhome in the heart of the historic downtown district. "
United States
Kelly M.
The price is AED 506
AED 1,190 total
includes taxes & fees
21 Jul - 22 Jul
Luxury Condo In Downtown Frederick
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, (93 reviews)
"This is a beautiful, clean, traquil and relaxing home away from home. The beds are comfortable, the living space is open and full of light during the day. The hosts have made great efforts to make this a family and/or couple friendly destination. Our dog was welcomed and enjoyed her stay (being with her people). The views are spectacular."
United States
Deb K.
The price is AED 614
AED 1,337 total
includes taxes & fees
13 Jul - 14 Jul
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

10/10 Excellent
"Clean room, friendly staff and a good breakfast."
Scott 1-night trip
Posted 2 hours ago
Fairfield Inn & Suites by Marriott Hagerstown

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 Washington Monument State Park and Orchid Cellar Winery.

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.