A stone tower with a staircase leading up to it.

Holiday Homes in Middletown

  • 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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Middletown holiday homes

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, (160 reviews)
"Great little spot!"
United States
Shelby W.
The price is NZ$545
includes taxes & fees
3 Nov - 4 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown
A bathroom with a toilet, a shower, and a bathtub. There is a shelf with towels and toiletries.

2. 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 NZ$445
includes taxes & fees
26 Oct - 27 Oct
Cozy Downtown Cabin - Family Friendly
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

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, (74 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is NZ$453
includes taxes & fees
26 Oct - 27 Oct
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A patio area with a wooden table, chairs, a decorative vase, and a fire pit.

4. 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.
The price is NZ$494
includes taxes & fees
28 Oct - 29 Oct
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A modern kitchen with grey cabinets, a central island, and pendant lighting.

5. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (99 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 NZ$609
includes taxes & fees
27 Oct - 28 Oct
Luxury Condo In Downtown Frederick
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

6. 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, (146 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is NZ$536
includes taxes & fees
1 Nov - 2 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

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, (21 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
The price is NZ$781
includes taxes & fees
2 Nov - 3 Nov
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A modern kitchen with a granite countertop, stainless steel appliances, and a white backsplash.

8. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (12 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 NZ$743
includes taxes & fees
28 Oct - 29 Oct
New townhouse
A wooden cabin with a patio area, outdoor seating, and a fire pit.

9. 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 NZ$579
includes taxes & fees
25 Oct - 26 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A two-story house with a front porch, a staircase, and a mailbox.

10. 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
Dog-Friendly | Hiking| Tubing near Harpers Ferry
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

11. 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 NZ$863
includes taxes & fees
25 Oct - 26 Oct
Newly constructed 6 bedroom home
A wooden deck with a grill, outdoor seating, and a bottle of wine.

12. 1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
Sharpsburg
10.0 out of 10, Exceptional, (54 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 NZ$546
includes taxes & fees
26 Oct - 27 Oct
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
A deck with green chairs and a fire pit, surrounded by a house and trees.

13. 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, (34 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is NZ$914
includes taxes & fees
3 Nov - 4 Nov
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A deck with outdoor seating and a lake view.

14. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
10.0 out of 10, Exceptional, (14 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 NZ$456
includes taxes & fees
26 Oct - 27 Oct
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A spacious living room with a ceiling fan, a blue sofa set, a grey armchair, and a large window with a view of the outdoors.

15. New, Contemporary House in Historic Harpers Ferry

New, Contemporary House in Historic Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (8 reviews)
"The home was perfect for our visit.We were in and out all weekend but really appreciated the well stocked kitchen supplies, the comfortable beds and the hot water levels. We were able to relax in the spacious living room and spend some time on the little outdoor areas. We would stay again but if the group was much bigger there may be issues as there are only bathrooms on the first floor. "
United States
Erin J.
The price is NZ$639
includes taxes & fees
25 Oct - 26 Oct
New, Contemporary House in Historic Harpers Ferry
A traditional living room with a fireplace, floral-patterned furniture, and a large rug.

16. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is NZ$546
includes taxes & fees
26 Oct - 27 Oct
Charming Shepherdstown Home - Walk to Downtown
A kitchen with white cabinets, a black refrigerator, a wooden table, and a ceiling fan.

17. Schilling House

Schilling House
3.0 star property
Bolivar
The price is NZ$540
includes taxes & fees
3 Nov - 4 Nov
Schilling House
A house with a well-lit entrance, a small garden, and a gravel driveway.

18. 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, (24 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is NZ$452
includes taxes & fees
26 Oct - 27 Oct
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

19. 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 NZ$744
includes taxes & fees
25 Oct - 26 Oct
Rural & Historic Detour Escape w/ Horses On-Site!
A four-poster canopy bed with a view of a cityscape through the window.

20. Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (22 reviews)
"Great spot on a cute street. Easy check in and out, and the place is stocked with everything you might need!"
United States
Ashley B.
The price is NZ$530
includes taxes & fees
1 Nov - 2 Nov
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
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

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

8/10 Good
"The room was very nice and roomy. The breakfast we had was very good. Nice selection of food. Staff was very nice. The only complaint was the noise from the dumpsters being emptied around 4 in the morning from business next door."
Robert 1-night trip
Posted 10 hours ago
Country Inn & Suites by Radisson, Hagerstown, MD

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
697
Accommodation
285 Holiday Homes
Lowest Price
NZ$445
Highest Price
NZ$914