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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Middletown vacation rentals

A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (157 reviews)
"Great place to stay. Very clean and beautiful. The Host was very nice too and kept us informed. We will definetly stay there again!"
United States
Adair M.
The price is AED 349
AED 927 total
includes taxes & fees
12 Oct - 13 Oct
Charming "Cream of the Crop" Cape ~❤️of Middletown
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

2. 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 1,040 total
includes taxes & fees
26 Oct - 27 Oct
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A bedroom with a bed, a dresser, a ceiling fan, and a window with blinds.

3. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (1 review)
"Cute little cabin. Perfect for our 1 night stay for a concert in the area. Im just sad we left the kids at home cause they would have loved it too!"
United States
Laura K.
The price is AED 777
AED 936 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Downtown Cabin - Family Friendly
A bedroom with a bed, a bedside table with a lamp, a window with a view, and a decorative wall piece.

4. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean place. "
United States
Warren B.
Cozy, dog-friendly, downtown
A modern apartment with a living room, kitchen, and dining area.

5. Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (9 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
Pet-friendly, heart of 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, (86 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 AED 169
AED 411 total
includes taxes & fees
25 Oct - 26 Oct
❤️ Secluded 1940s Romantic Tiny House on the River
A room with a blue wall, a wooden dining table, a blue sofa, a white fireplace, and a window with white curtains.

7. Huge, Downtown, Walkable, Coffee, Breweries, Dogs

Huge, Downtown, Walkable, Coffee, Breweries, Dogs
Downtown Frederick
10.0 out of 10, Exceptional, (4 reviews)
"Very comfortable and convenient stay with responsive hosts. Great amenities for longer stays with the w/d. Will be back!"
United States
Dave T.
Huge, Downtown, Walkable, Coffee, Breweries, Dogs
A patio area with a wooden table, chairs, a decorative vase, and a fire pit.

8. Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
10.0 out of 10, Exceptional, (54 reviews)
"Great lodging and communicative host"
United States
Peggy D.
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

9. 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, (74 reviews)
The price is AED 349
AED 927 total
includes taxes & fees
12 Oct - 13 Oct
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

10. 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, (70 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 AED 364
AED 658 total
includes taxes & fees
13 Oct - 14 Oct
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.

11. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (71 reviews)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
The price is AED 446
AED 979 total
includes taxes & fees
13 Oct - 14 Oct
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

12. 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 AED 424
AED 730 total
includes taxes & fees
12 Oct - 13 Oct
Beautiful, Historic, Hiking, Biking and C&O Canal
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

13. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (104 reviews)
Modern Condo Right off Market Street
A modern kitchen with grey cabinets, a central island, and pendant lighting.

14. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (98 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is AED 592
AED 1,289 total
includes taxes & fees
4 Nov - 5 Nov
Luxury Condo In Downtown Frederick
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

15. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (45 reviews)
The price is AED 408
AED 1,370 total
includes taxes & fees
14 Oct - 15 Oct
Antietam Look Out - Incredible Sunset Views!
A bedroom with a large bed, a painting on the wall, a bedside table, and a window with curtains.

16. 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)
The price is AED 485
AED 915 total
includes taxes & fees
13 Oct - 14 Oct
Historic Getaway near C&O Canal, hiking and biking
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

17. 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, (76 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 AED 533
AED 1,576 total
includes taxes & fees
12 Oct - 13 Oct
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

18. 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, (141 reviews)
The price is AED 514
AED 1,149 total
includes taxes & fees
1 Nov - 2 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

19. 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, (18 reviews)
The price is AED 550
AED 1,227 total
includes taxes & fees
14 Oct - 15 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A living room with a dining table, chairs, a sofa, and a television.

20. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
The price is AED 485
AED 863 total
includes taxes & fees
13 Oct - 14 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance
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

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

8/10 Good
"Rooms were great! Staff was friendly. Parking was good. The only downside was the breakfast options. Selections were slim."
Micah 1-night trip
Posted 14 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?

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.