A stone tower with a staircase leading up to it.

Holiday Homes in Middletown

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Our top choices for Middletown holiday homes

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (162 reviews)
"Great little spot!"
United States
Shelby W.
The price is AU$384
includes taxes & fees
15 Nov - 16 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown

2. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is AU$321
includes taxes & fees
25 Nov - 26 Nov
Cozy Downtown Cabin - Family Friendly

3. 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 AU$376
includes taxes & fees
15 Nov - 16 Nov
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

4. 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, (149 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 AU$373
includes taxes & fees
14 Dec - 15 Dec
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

5. 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 AU$491
includes taxes & fees
9 Dec - 10 Dec
Luxury Condo In Downtown Frederick

6. 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)
"Cute place with a lot of character. Host was very responsive. We enjoyed our sray."
United States
Dawn V.
The price is AU$459
includes taxes & fees
15 Nov - 16 Nov
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

7. 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 AU$622
includes taxes & fees
23 Nov - 24 Nov
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

8. Dog-Friendly | Hiking| Tubing near Harpers Ferry

Dog-Friendly | Hiking| Tubing near Harpers Ferry
Brunswick
2.0 out of 10, (1 review)
"No ac just window units it was soooooo hot"
United States
Anonymous traveller
The price is AU$327
includes taxes & fees
17 Nov - 18 Nov
Dog-Friendly | Hiking| Tubing near Harpers Ferry

9. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (13 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 AU$575
includes taxes & fees
16 Nov - 17 Nov
New townhouse

10. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (22 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
United States
Janice M.
The price is AU$686
includes taxes & fees
23 Nov - 24 Nov
Newly constructed 6 bedroom home

11. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
Knoxville
10.0 out of 10, Exceptional, (37 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is AU$717
includes taxes & fees
16 Nov - 17 Nov
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

12. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
Shepherdstown
9.4 out of 10, Exceptional, (6 reviews)
"Very nice place, the lay out is perfect for multiple adults, we stayed for 10 night for work and it was perfect, we will be back for another long stay soon. "
United States
Brandon K.
The price is AU$529
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!

13. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AU$461
includes taxes & fees
15 Nov - 16 Nov
Schilling House

14. Rural & Historic Detour Escape w/ Horses On-Site!

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.0 out of 10, Wonderful, (8 reviews)
"Lovely! Our host was gracious and helpful. Property was ideal for our family getaway. i’m"
United States
Mary F.
The price is AU$601
includes taxes & fees
8 Dec - 9 Dec
Rural & Historic Detour Escape w/ Horses On-Site!

15. Hidden Creekside retreat near 5 national parks, including Harpers Ferry

Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Martinsburg
10.0 out of 10, Exceptional, (14 reviews)
"Wonderful location and property."
United States
Helen F.
The price is AU$381
includes taxes & fees
15 Nov - 16 Nov
Hidden Creekside retreat near 5 national parks, including Harpers Ferry

16. Camp Patowmack - Riverfront, Hot Tub, and Sauna!

Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Harpers Ferry
9.6 out of 10, Exceptional, (11 reviews)
"Great water access"
United States
claire r.
Camp Patowmack - Riverfront, Hot Tub, and Sauna!

17. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (25 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is AU$370
includes taxes & fees
18 Nov - 19 Nov
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

18. Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Highfield-Cascade
10.0 out of 10, Exceptional, (11 reviews)
"I cannot say enough about the wonderful time we had staying at Denise & Mike's lovely cottage. They went above and beyond to make sure our family gathering was perfect...and it truly was. Sitting on the front porch sharing coffee in the a.m. and wine in the evening. Board games, chats and laughter until our bellies ached. Our family spent our much needed reunion sharing long overdue times making more wonderful memories. Upon arrival we found the property even more special than we imagined from...
United States
Julianne L.
The price is AU$366
includes taxes & fees
24 Nov - 25 Nov
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

19. Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery

Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery
Harpers Ferry
9.8 out of 10, Exceptional, (16 reviews)
"We had a lovely stay and it was so nice for our dog as well. The Mountain Lake Cub had a doggy beach day on Saturday morning and it was a super fun experience. The host was friendly and responsive!"
United States
Dawn S.
The price is AU$498
includes taxes & fees
22 Nov - 23 Nov
Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery

20. 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
8.2 out of 10, Very good, (66 reviews)
"I was surprised to see how dilapidated the decking around the house was. I was concerned we might trip or fall through. The location was ideal for bicycling and fishing . The backyard was beautiful with the most prettiest flowers and trees."
United States
Susie R.
The price is AU$604
includes taxes & fees
16 Nov - 17 Nov
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
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

Middletown Holiday Homes information

Number of reviews
740
Accommodation
285 Holiday Homes
Lowest Price
AU$321
Highest Price
AU$717