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
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Middletown vacation rentals

Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (154 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 661
AED 1,312 total
includes taxes & fees
30 Aug - 31 Aug
Charming "Cream of the Crop" Cape ~❤️of Middletown
Smart TV

2. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
The price is AED 661
AED 802 total
includes taxes & fees
30 Aug - 31 Aug
Cozy Downtown Cabin - Family Friendly
Coffee/tea maker, fridge, microwave, toaster

3. Patty's Place - Private and Convenient Apartment near Downtown

Patty's Place - Private and Convenient Apartment near Downtown
Frederick
10.0 out of 10, Exceptional, (15 reviews)
"I’m a little sad to go I had the best stay. So comfortable so quiet, great stay. I will definitely be back "
United States
Anonymous traveler
The price is AED 224
AED 764 total
includes taxes & fees
25 Aug - 26 Aug
Patty's Place - Private and Convenient Apartment near Downtown
Coffee/tea maker, fridge, microwave, oven

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, (71 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is AED 533
AED 1,156 total
includes taxes & fees
30 Aug - 31 Aug
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
1 bedroom, WiFi (free), bed sheets

5. 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
Exterior detail

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

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (11 reviews)
"Great location for a peaceful solo night away -- thanks!"
United States
Kristina S.
Huge 1br apt, baby-friendly, dogs, walkable downtown
Exterior

7. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (83 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is AED 238
AED 488 total
includes taxes & fees
31 Aug - 1 Sep
❤️ Secluded 1940s Romantic Tiny House on the River
Interior

8. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (44 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
The price is AED 375
AED 1,329 total
includes taxes & fees
1 Sep - 2 Sep
Antietam Look Out - Incredible Sunset Views!
Coffee/tea maker, fridge, microwave, oven

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

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (69 reviews)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
The price is AED 479
AED 1,026 total
includes taxes & fees
31 Aug - 1 Sep
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Outdoor dining

10. Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (23 reviews)
"We really enjoyed our recent stay. Check-in was simple, the host very responsive, location is excellent (we walked everywhere) and well designed. Would stay again."
United States
Richard M.
The price is AED 456
AED 1,110 total
includes taxes & fees
7 Sep - 8 Sep
Chic, pets, walk to downtown
TV, fireplace

11. 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, (75 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 404
AED 1,411 total
includes taxes & fees
31 Aug - 1 Sep
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A park with a pond, a bridge, and a church in the background.

12. RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (134 reviews)
"The place was so fun and close to the bars! The rooms where cleans "
United States
Anonymous traveler
The price is AED 448
AED 1,078 total
includes taxes & fees
30 Aug - 31 Aug
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Outdoor dining

13. 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, (51 reviews)
"Great lodging and communicative host"
United States
Peggy D.
The price is AED 474
AED 1,063 total
includes taxes & fees
27 Aug - 28 Aug
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Coffee/tea maker, fridge, microwave, oven

14. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (102 reviews)
"Great place!"
United States
Danielle G.
The price is AED 592
AED 1,231 total
includes taxes & fees
25 Aug - 26 Aug
Modern Condo Right off Market Street
Smart TV, music library

15. Downtown Frederick retreat with parking. Dog- and baby-friendly!

Downtown Frederick retreat with parking. Dog- and baby-friendly!
Frederick
9.8 out of 10, Exceptional, (7 reviews)
"This place looked exactly like the photos, very clean, super organized, and well designed. We were very comfortable during our stay and would stay here again."
United States
Dvorak A.
The price is AED 386
AED 1,047 total
includes taxes & fees
25 Aug - 26 Aug
Downtown Frederick retreat with parking. Dog- and baby-friendly!
Dining

16. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (97 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is AED 592
AED 1,297 total
includes taxes & fees
25 Aug - 26 Aug
Luxury Condo In Downtown Frederick
Property grounds

17. 5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Sharpsburg
10.0 out of 10, Exceptional, (50 reviews)
"The house was in a great location with the winery and battlefield nearby, and the house was very nice and comfortable."
United States
Nancy D.
The price is AED 275
AED 936 total
includes taxes & fees
1 Sep - 2 Sep
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Interior

18. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (96 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 AED 735
AED 1,226 total
includes taxes & fees
1 Sep - 2 Sep
Antietam Creek - Quiet 2 Bedroom Cabin
Exterior

19. 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
9.6 out of 10, Exceptional, (210 reviews)
"Great place, pet friendly. "
United States
Doug P.
The price is AED 533
AED 642 total
includes taxes & fees
14 Sep - 15 Sep
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Exterior

20. Towpath Loft -Bike Storage, Downtown Brunswick, MD

Towpath Loft -Bike Storage, Downtown Brunswick, MD
Brunswick
The price is AED 275
AED 736 total
includes taxes & fees
1 Sep - 2 Sep
Towpath Loft -Bike Storage, Downtown Brunswick, MD
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

Best Western Historic Frederick

Best Western Historic Frederick

8/10 Good
"Bathroom was very small. Gaps under the door allowed too much hall noise to come into the room."
James 1-night trip
Posted 7 hours ago
Best Western Historic Frederick

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?

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.: This vacation home rental near Middletown is located in the city center and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. 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 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 Washington Monument State Park and South Mountain State Park.

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.