Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Middletown vacation rentals

A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

1. 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, (118 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 CA $141
CA $326 total
includes taxes & fees
Nov 15 - Nov 16
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (161 reviews)
"Great little spot!"
United States
Shelby W.
The price is CA $120
CA $334 total
includes taxes & fees
Nov 11 - Nov 12
Charming "Cream of the Crop" Cape ~❤️of Middletown
A log cabin interior with a wooden bench, a leather sofa, a coffee table, and a bookshelf.

3. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is CA $268
CA $310 total
includes taxes & fees
Nov 25 - Nov 26
Cozy Downtown Cabin - Family Friendly
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

4. 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, (75 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is CA $134
CA $358 total
includes taxes & fees
Nov 12 - Nov 13
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A compact kitchen with a coffee machine, microwave, and a small cart with kitchen tools.

5. 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, (18 reviews)
"Place was perfect and tbe location great. East in and out town..or to get to down town"
United States
Andrew
The price is CA $115
CA $312 total
includes taxes & fees
Nov 22 - Nov 23
Patty's Place - Private and Convenient EV-Friendly Apartment near 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, (88 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 CA $58
CA $139 total
includes taxes & fees
Nov 15 - Nov 16
❤️ Secluded 1940s Romantic Tiny House on the River
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

7. 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, (148 reviews)
"Great location. Amenities were perfect for a little bit of an extended stay. Definitely will come back in the future"
United States
Dave T.
The price is CA $141
CA $358 total
includes taxes & fees
Nov 12 - Nov 13
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

8. Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
10.0 out of 10, Exceptional, (71 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 CA $140
CA $243 total
includes taxes & fees
Nov 9 - Nov 10
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.

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

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (72 reviews)
"The house is very cute and a perfect fit for our needs. We appreciated how clean the house was too! It's conveniently located to some many restaurants and shops. We would gladly stay here again!"
United States
Sara W.
The price is CA $203
CA $396 total
includes taxes & fees
Nov 10 - Nov 11
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

10. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (46 reviews)
"The house was as great! Plenty of space for 5 adults. Conveniently located to the areas we wanted to visit. Very quiet location"
United States
Melisa T.
The price is CA $150
CA $565 total
includes taxes & fees
Nov 18 - Nov 19
Antietam Look Out - Incredible Sunset Views!
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

11. 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 CA $163
CA $269 total
includes taxes & fees
Nov 10 - Nov 11
Beautiful, Historic, Hiking, Biking and C&O Canal
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

12. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (107 reviews)
"Great location"
United States
John
The price is CA $233
CA $455 total
includes taxes & fees
Nov 9 - Nov 10
Modern Condo Right off Market Street
A bathroom with a glass shower enclosure, a white sink, and a door leading to a bedroom.

13. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (102 reviews)
"Very convenient location with parking. Prompt communication with owner. However it needs a good deep clean. My towels were used and muddy like the workmen fixing the deck had just showered there. But I would stay there again if necessary."
United States
Jessica
The price is CA $217
CA $463 total
includes taxes & fees
Dec 1 - Dec 2
Luxury Condo In Downtown Frederick
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

14. 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, (77 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 CA $194
CA $660 total
includes taxes & fees
Nov 19 - Nov 20
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A wooden door with a brass number plate, a small shelf with a birdcage, and framed pictures on the wall.

15. 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)
"Very friendly host who made communications easy. We left our iPad behind and they called us right away. The apartment was large, beds were comfortable, and the bathroom renovation was beautiful with a great shower. It is about a block from the C&O trail plus free parking on the property."
United States
Kelly
The price is CA $186
CA $337 total
includes taxes & fees
Nov 9 - Nov 10
Historic Getaway near C&O Canal, hiking and biking
A cozy room with a bed, a sofa, a wooden dresser, a desk with a lamp, and a kitchen area with wooden cabinets and a microwave.

16. Loft Apt Just off C&O near Harpers Ferry and AT

Loft Apt Just off C&O near Harpers Ferry and AT
Brunswick
10.0 out of 10, Exceptional, (23 reviews)
"The place was nice and cozy"
United States
Andrew E.
The price is CA $152
CA $272 total
includes taxes & fees
Nov 9 - Nov 10
Loft Apt Just off C&O near Harpers Ferry and AT
A living room with a dining table, chairs, a sofa, and a television.

17. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
The price is CA $186
CA $318 total
includes taxes & fees
Nov 10 - Nov 11
Quaint Mini Cottage in Shepherdstown - Walking Distance
A wooden cabin with a patio area, outdoor seating, and a fire pit.

18. 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, (19 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
The price is CA $211
CA $451 total
includes taxes & fees
Nov 9 - Nov 10
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

19. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (22 reviews)
"Our stay was so enjoyable!"
United States
Kimberly C.
The price is CA $389
CA $610 total
includes taxes & fees
Nov 16 - Nov 17
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

20. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (56 reviews)
"Very comfortable and cozy. Our family had a great stay here."
United States
bethany c.
The price is CA $208
CA $381 total
includes taxes & fees
Nov 12 - Nov 13
Charming Cabin in the Woods with River Access
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

A rooftop terrace with outdoor seating, a fire pit, and a view of the sunset over a mountainous landscape.
SpringHill Suites by Marriott Frederick

SpringHill Suites by Marriott Frederick

SpringHill Suites by Marriott Frederick
Frederick

10/10 Excellent

The room was clean, the beds comfortable and the staff
Canada
Allanah
Reviewed May 16, 2026
SpringHill Suites by Marriott Frederick

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown vacation rentals we have selected for you start as low as CA $58 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.