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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Middletown holiday homes

Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (152 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 NZ$543
includes taxes & fees
2 Aug - 3 Aug
Charming "Cream of the Crop" Cape ~❤️of Middletown
Coffee/tea maker, fridge, microwave, oven

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, (69 reviews)
"We had 6 in our group and it was perfect especially for the price. Super clean, great responsive host, good location. Bakery directly across the street and ice cream and sandwich shop just down the road at the light. Will definitely stay here again. "
United States
Anonymous traveller
The price is NZ$553
includes taxes & fees
9 Aug - 10 Aug
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A park with a pond, a bridge, and a church in the background.

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, (130 reviews)
"The place was so fun and close to the bars! The rooms where cleans "
United States
Anonymous traveller
The price is NZ$498
includes taxes & fees
9 Aug - 10 Aug
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Outdoor dining

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
9.8 out of 10, Exceptional, (49 reviews)
"Great location--easy walk to downtown Frederick. Comfortable beds, pleasant spaces and light."
United States
Alan S.
The price is NZ$479
includes taxes & fees
2 Aug - 3 Aug
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Dining

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 NZ$601
includes taxes & fees
24 Aug - 25 Aug
Luxury Condo In Downtown Frederick
Property grounds

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Sharpsburg
10.0 out of 10, Exceptional, (47 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$496
includes taxes & fees
17 Aug - 18 Aug
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Microwave, oven, stovetop, dishwasher

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, (13 reviews)
"Beautiful historic home. Hosts were very welcoming and the place was newly renovated. "
United States
Drew M.
The price is NZ$781
includes taxes & fees
2 Aug - 3 Aug
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Exterior

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 NZ$990
includes taxes & fees
24 Aug - 25 Aug
New townhouse
Coffee/tea maker, fridge, microwave, oven

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 NZ$842
includes taxes & fees
24 Aug - 25 Aug
Newly constructed 6 bedroom home
Exterior

Frederick Townhome w/ Balcony, Close to Parks!

Frederick Townhome w/ Balcony, Close to Parks!
Frederick
6.8 out of 10, (5 reviews)
"Great location to downtown Frederick."
United States
Johnna H.
Frederick Townhome w/ Balcony, Close to Parks!
Interior

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 NZ$742
includes taxes & fees
28 July - 29 July
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Smart TV, fireplace, DVD player, books

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

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (109 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 NZ$715
includes taxes & fees
5 Aug - 6 Aug
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (72 reviews)
"We had the best spring break trip here with our two sons. The property was comfortable and well-stocked. Communication and checking in was incredibly easy. There were a few things we had questions/concerns about and everything was responded to and addressed/answered immediately. We spent so much time outside-it was a great "reset" for us to get away from the city and into nature. We would definitely come back to this property! "
United States
Elisa W.
Terra Alta - Incredible River Views and Hot Tub!
Terrace/patio

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, (40 reviews)
"Great place to stay for the weekend."
United States
Bea G.
The price is NZ$619
includes taxes & fees
30 July - 31 July
Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Outdoor dining

New Playground•Fenced Yard•Hot Tub•King Bed•Pets

New Playground•Fenced Yard•Hot Tub•King Bed•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (30 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is NZ$712
includes taxes & fees
27 July - 28 July
New Playground•Fenced Yard•Hot Tub•King Bed•Pets
Outdoor dining

5 Mi to Harpers Ferry NHP: Quiet Deck & Garden

5 Mi to Harpers Ferry NHP: Quiet Deck & Garden
Harpers Ferry
5 Mi to Harpers Ferry NHP: Quiet Deck & Garden
Exterior

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)
"Host was super nice and location was pretty. "
United States
Kimberly B.
The price is NZ$447
includes taxes & fees
28 July - 29 July
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Interior

Camp Patowmack - Riverfront, Hot Tub, and Sauna!

Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Harpers Ferry
9.4 out of 10, Exceptional, (10 reviews)
"Great house with a beautiful view. "
United States
Sandra A.
Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Interior

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 NZ$761
includes taxes & fees
2 Aug - 3 Aug
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
"Clean spacious seemingly newly renovated room with large bathroom, nice products in the bathroom, very comfortable bed and refrigerator and microwave. Good breakfast included. Located in a mall area with a Popeyes Chicken in the same lot. Recommend!"
susan 1-night trip
Posted 9 hours ago
Country Inn & Suites by Radisson, Hagerstown, MD

Find out more about Middletown

Middletown Holiday Homes information

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