A stone tower with a staircase leading up to it.

Search Vacation 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 HK$1,176
HK$2,500 total
includes taxes & fees
3 Nov - 4 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown
A bedroom with a bed, a dresser, a ceiling fan, and a window with blinds.

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 HK$1,715
HK$2,067 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Downtown Cabin - Family Friendly
A patio area with a wooden table, chairs, a decorative vase, and a fire pit.

3. 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.

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, (74 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is HK$785
HK$2,030 total
includes taxes & fees
26 Oct - 27 Oct
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
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 HK$1,264
HK$2,754 total
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 HK$1,097
HK$2,459 total
includes taxes & fees
8 Nov - 9 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A cozy attic bedroom with a skylight, a wicker chair, a round table, and a bed with a headboard.

7. 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 HK$1,174
HK$2,621 total
includes taxes & fees
9 Nov - 10 Nov
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A two-story house with a front porch, a staircase, and a mailbox.

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 HK$984
HK$1,845 total
includes taxes & fees
27 Oct - 28 Oct
Dog-Friendly | Hiking| Tubing near Harpers Ferry
A modern kitchen with a granite countertop, stainless steel appliances, and a white backsplash.

9. 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 HK$1,434
HK$3,383 total
includes taxes & fees
28 Oct - 29 Oct
New townhouse
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

10. 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 HK$2,158
HK$3,543 total
includes taxes & fees
2 Nov - 3 Nov
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
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 HK$1,669
HK$3,871 total
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 HK$989
HK$2,489 total
includes taxes & fees
26 Oct - 27 Oct
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
A hallway with wooden flooring, a staircase, a door with a white frame, a lamp on a small table, and a wall-mounted mirror.

13. Antietam House Historic Sharpsburg Retreat

Antietam House Historic Sharpsburg Retreat
Sharpsburg
9.0 out of 10, Wonderful, (4 reviews)
"My friends and I had a wonderful time here for Labor Day! Quiet and a great location for all sorts of activities."
United States
Nick W.
Antietam House Historic Sharpsburg Retreat
A deck with green chairs and a fire pit, surrounded by a house and trees.

14. 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, (33 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is HK$1,281
HK$4,078 total
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.

15. 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 HK$274
HK$2,041 total
includes taxes & fees
26 Oct - 27 Oct
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

16. 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 HK$785
HK$2,893 total
includes taxes & fees
28 Oct - 29 Oct
New, Contemporary House in Historic Harpers Ferry
A kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.

17. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
Charming Shepherdstown Home - Walk to Downtown
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

18. Schilling House

Schilling House
3.0 star property
Bolivar
The price is HK$2,147
HK$2,689 total
includes taxes & fees
25 Oct - 26 Oct
Schilling House
A two-story house with a porch, green shutters, and a red roof.

19. Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (59 reviews)
"Great place in historic Harper’s ferry. Only negative thing I can say is the parking is not ideal"
United States
Brett D.
The price is HK$1,748
HK$3,212 total
includes taxes & fees
29 Oct - 30 Oct
Enchanting Cottage, walk to Downtown Harpers Ferry
A house with a well-lit entrance, a small garden, and a gravel driveway.

20. 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.
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
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

10/10 Excellent
"Comfortable and clean room in a convenient location. The room was large, quiet and had nice amenities and convenient outlets."
Paula 1-night trip
Posted 8 hours ago
Country Inn & Suites by Radisson, Hagerstown, MD

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
670
Accommodation
279 Vacation Homes
Lowest Price
HK$2,030
Highest Price
HK$4,078

Explore a world of travel with Expedia