A stone tower with a staircase leading up to it.

Holiday Homes in Middletown

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (157 reviews)
"Great place to stay. Very clean and beautiful. The Host was very nice too and kept us informed. We will definetly stay there again!"
United States
Adair M.
The price is AU$412
includes taxes & fees
6 Oct - 7 Oct
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, (1 review)
"Cute little cabin. Perfect for our 1 night stay for a concert in the area. Im just sad we left the kids at home cause they would have loved it too!"
United States
Laura K.
The price is AU$364
includes taxes & fees
6 Oct - 7 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, (73 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is AU$410
includes taxes & fees
4 Oct - 5 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, (52 reviews)
"Great lodging and communicative host"
United States
Peggy D.
The price is AU$385
includes taxes & fees
30 Sept - 1 Oct
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

5. 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, (141 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is AU$414
includes taxes & fees
30 Sept - 1 Oct
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

6. 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$704
includes taxes & fees
30 Sept - 1 Oct
Newly constructed 6 bedroom home
A modern kitchen with grey cabinets, a central island, and pendant lighting.

7. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (98 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is AU$491
includes taxes & fees
6 Oct - 7 Oct
Luxury Condo In Downtown Frederick
A bedroom with a bed, a bedside table with a lamp, a mirror, and a framed picture on the wall.

8. 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, (18 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
The price is AU$470
includes taxes & fees
30 Sept - 1 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

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, (18 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
The price is AU$634
includes taxes & fees
6 Oct - 7 Oct
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A brick building with a waterfall feature in front.

10. 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 AU$612
includes taxes & fees
6 Oct - 7 Oct
New townhouse
A large, curved metal building with a covered entrance and two chairs outside.

11. Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!

Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!
Sharpsburg
9.4 out of 10, Exceptional, (6 reviews)
"We enjoyed the views."
United States
Shena M.
Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

12. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AU$447
includes taxes & fees
13 Oct - 14 Oct
Schilling House
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

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

New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Bolivar
9.8 out of 10, Exceptional, (48 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
The price is AU$416
includes taxes & fees
5 Oct - 6 Oct
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

14. 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)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
The price is AU$633
includes taxes & fees
6 Oct - 7 Oct
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A modern kitchen with a large island, white cabinets, and a dining area with a bench and chairs.

15. Riverview Retreat - Pool, Hot Tub, and Mtn Views!

Riverview Retreat - Pool, Hot Tub, and Mtn Views!
Harpers Ferry
10.0 out of 10, Exceptional, (6 reviews)
"Had a fantastic time and everything was great! Highly recommend this spot for a vacation if you’re headed for Harper’s ferry."
United States
James A.
The price is AU$583
includes taxes & fees
30 Sept - 1 Oct
Riverview Retreat - Pool, Hot Tub, and Mtn Views!
A room with a large sliding glass door leading to a backyard with a grassy lawn and trees. There are two gray upholstered chairs in the room.

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 AU$523
includes taxes & fees
1 Oct - 2 Oct
New, Contemporary House in Historic Harpers Ferry
A bedroom with a large bed, a bench, a chair, a nightstand, and a wall with decorative plates.

17. Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (21 reviews)
"Overall good property- close location to all attractions"
United States
Trisha P.
The price is AU$583
includes taxes & fees
30 Sept - 1 Oct
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
A cozy interior with a wooden bench, a cushioned seating area, and a large window offering a view of trees.

18. Perfect 2-bedroom Treetop Bungalow Treehouse

Perfect 2-bedroom Treetop Bungalow Treehouse
Leesburg
10.0 out of 10, Exceptional, (3 reviews)
"Fun, creative place to stay. Worked well for our family of four for the weekend."
United States
Kathy S.
The price is AU$585
includes taxes & fees
5 Oct - 6 Oct
Perfect 2-bedroom Treetop Bungalow Treehouse
A living room with two dark sofas, a wooden coffee table, and a chandelier.

19. Cozy Getaway Near History, Hiking & Adventure

Cozy Getaway Near History, Hiking & Adventure
Bolivar
10.0 out of 10, Exceptional, (2 reviews)
"This house was perfect for our getaway. Clean and comfortable. Close to everything."
United States
Ashlee O.
The price is AU$434
includes taxes & fees
30 Sept - 1 Oct
Cozy Getaway Near History, Hiking & Adventure
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

20. 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)
"We had a great time. It is an older house but wonderful. It is in the country with lots of green fields surrounding it. The porch with the rockers was my favorite place to be when we weren’t site seeing, It was so peaceful. I would definitely stay here again."
United States
Charla H.
The price is AU$612
includes taxes & fees
30 Sept - 1 Oct
Rural & Historic Detour Escape w/ Horses On-Site!
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

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

10/10 Excellent
"Great breakfast, staff very polite, everything great. But… DO NOT PARK under the tree…. My truck was covered in bird poop… had to go thru car wash 2x to get it all off. I’ll know better next t8me"
Donna 1-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Hagerstown, MD

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
690
Accommodation
285 Holiday Homes
Lowest Price
AU$364
Highest Price
AU$704