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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Middletown holiday homes

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 €288
includes taxes & fees
26 Aug - 27 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 €205
includes taxes & fees
17 Aug - 18 Aug
Cozy Downtown Cabin - Family Friendly
Terrace/patio

3. Cozy Getaway Near History, Hiking & Adventure

Cozy Getaway Near History, Hiking & Adventure
Bolivar
10.0 out of 10, Exceptional, (1 review)
"This is a great property. Very clean and well taken care of. Backyard is fantastic too! You won’t be sorry you stayed here. Close to historic town and lots of great places to eat. Beautiful area!"
United States
Kelly
The price is €278
includes taxes & fees
8 Sept - 9 Sept
Cozy Getaway Near History, Hiking & Adventure
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
9.8 out of 10, Exceptional, (70 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is €220
includes taxes & fees
16 Aug - 17 Aug
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Outdoor dining

5. 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)
"We had a wonderful Mother’s Day weekend visiting our daughter and her family! The home was exactly as pictured, very clean and a great location! We could easily walk to our daughter’s house and anything in downtown Frederick. Would definitely stay here agin! "
United States
Dawn W.
The price is €243
includes taxes & fees
14 Sept - 15 Sept
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A park with a pond, a bridge, and a church in the background.

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
9.4 out of 10, Exceptional, (134 reviews)
"The place was so fun and close to the bars! The rooms where cleans "
United States
Anonymous traveller
The price is €251
includes taxes & fees
14 Sept - 15 Sept
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Dining

7. 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 €349
includes taxes & fees
14 Sept - 15 Sept
Luxury Condo In Downtown Frederick
Exterior

8. 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, (209 reviews)
"Great place, pet friendly. "
United States
Doug P.
The price is €155
includes taxes & fees
14 Sept - 15 Sept
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Microwave, oven, stovetop, dishwasher

9. 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, (16 reviews)
"Beautiful historic home. Hosts were very welcoming and the place was newly renovated. "
United States
Drew M.
The price is €385
includes taxes & fees
23 Aug - 24 Aug
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Coffee/tea maker, fridge, microwave, oven

10. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (19 reviews)
"Everything was excellent "
United States
Ronald G.
The price is €420
includes taxes & fees
26 Aug - 27 Aug
Newly constructed 6 bedroom home
Exterior

11. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (11 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 €486
includes taxes & fees
26 Aug - 27 Aug
New townhouse
Terrace/patio

12. Modern Retreat - 4 King Suites, Saltwater Hot Tub & Game Room – Harpers Ferry

Modern Retreat - 4 King Suites, Saltwater Hot Tub & Game Room – Harpers Ferry
Knoxville
10.0 out of 10, Exceptional, (25 reviews)
"Easy to get in, instructions and expectations were clear, amenities were as expected, and the home was beautiful. "
United States
Katherine Z.
Modern Retreat - 4 King Suites, Saltwater Hot Tub & Game Room – Harpers Ferry
Interior

13. Rural Home, Hot Tub, Campfire, Hardwood Floors

Rural Home, Hot Tub, Campfire, Hardwood Floors
Harpers Ferry
9.4 out of 10, Exceptional, (86 reviews)
"We enjoyed this house very comfy cozy we stayed because we had a celebration of life and me and my family were able to just unwind here thank u so much we loved it and the jacuzzi was wonderful "
United States
Jennifer B.
The price is €331
includes taxes & fees
19 Aug - 20 Aug
Rural Home, Hot Tub, Campfire, Hardwood Floors
Smart TV, fireplace, DVD player, books

14. Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (111 reviews)
"Wonderful place to stay. Comfotable beds and big enough for a large crowd. The property owners are incredibly kind and responsive. Our family loved our stay. "
United States
Jenn C.
The price is €346
includes taxes & fees
26 Aug - 27 Aug
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Interior

15. 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
8.4 out of 10, Very good, (63 reviews)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
The price is €403
includes taxes & fees
13 Sept - 14 Sept
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Exterior

16. Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (54 reviews)
"Area was great, host was super helpful and communicative "
United States
Riya L.
The price is €325
includes taxes & fees
13 Sept - 14 Sept
Enchanting Cottage, walk to Downtown Harpers Ferry
Terrace/patio

17. Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Bolivar
9.8 out of 10, Exceptional, (42 reviews)
"Great place to stay for the weekend."
United States
Bea G.
The price is €315
includes taxes & fees
19 Aug - 20 Aug
Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Interior

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

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.6 out of 10, Exceptional, (5 reviews)
"Check-in was super easy. Communication with the owners was quick and easy. There was one hiccup that came up and were very quick to resolve. The house itself is a great historic home. They have done a great job modernizing it. My only feedback would be to have more supplies in the kitchen to accommodate preparing foods like knives, cutting boards, trays, etc. But otherwise, very happy with our stay and the beautiful property, and it being dog friendly!"
United States
Rachel W.
The price is €381
includes taxes & fees
16 Aug - 17 Aug
Rural & Historic Detour Escape w/ Horses On-Site!
Terrace/patio

19. Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath

Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
Bolivar
10.0 out of 10, Exceptional, (56 reviews)
"Beautiful home; beds are very comfortable. Atmosphere very comforting. Kitchen well stocked. Would come again and will tell others great place to stay."
United States
Penny M.
The price is €310
includes taxes & fees
24 Aug - 25 Aug
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
Exterior

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.
The price is €222
includes taxes & fees
17 Aug - 18 Aug
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

SpringHill Suites by Marriott Frederick

SpringHill Suites by Marriott Frederick

8/10 Good
"The property and the rooms were very clean. The staff was helpful and answered all questions. Only reason I would give 4/5 starts was because of the room set up. With the bathroom door being a large sliding barn door with a large window that was frosted slightly. The main issue was in the middle of the night or early morning, if someone takes a shower or goes to the restroom, the light from the bathroom fills the room and easily wakes people up."
Aaron 1-night trip
Posted 9 hours ago
SpringHill Suites by Marriott Frederick

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
1,158
Accommodation
285 Holiday Homes
Lowest Price
€155
Highest Price
€486