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
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 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, (150 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 HK$1,097
HK$2,410 total
includes taxes & fees
19 Jul - 20 Jul
Charming "Cream of the Crop" Cape ~❤️of Middletown
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)
"Great stay, excellent location and host was always readily available. Highly recommended!"
United States
Zayde C.
The price is HK$776
HK$2,052 total
includes taxes & fees
14 Jul - 15 Jul
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Outdoor dining

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
9.8 out of 10, Exceptional, (8 reviews)
"A wonderfully equipped home in a lovely location. Everything you could ever need was on hand. "
United States
alison m.
The price is HK$1,411
HK$3,240 total
includes taxes & fees
10 Aug - 11 Aug
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Fridge, microwave, oven, stovetop

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 HK$666
HK$1,878 total
includes taxes & fees
14 Jul - 15 Jul
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (96 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is HK$1,122
HK$2,593 total
includes taxes & fees
23 Jul - 24 Jul
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)
"Lovely little place! Host very responsive. Great location to visit Harper’s Ferry, Hancock and Shepherdstown."
United States
Debra C.
The price is HK$745
HK$2,197 total
includes taxes & fees
14 Jul - 15 Jul
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Smart TV, books, computer monitors

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean and comfortable. Would absolutely stay here again or recommend it to others. "
United States
Lauren S.
The price is HK$1,235
HK$2,646 total
includes taxes & fees
14 Jul - 15 Jul
Leesburg Hideaway- King Bed + Private Backyard
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 HK$705
HK$2,068 total
includes taxes & fees
14 Jul - 15 Jul
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Interior

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

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.6 out of 10, Exceptional, (4 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 HK$948
HK$3,423 total
includes taxes & fees
20 Jul - 21 Jul
Rural & Historic Detour Escape w/ Horses On-Site!
Fridge, oven, stovetop, dishwasher

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is HK$1,261
HK$2,612 total
includes taxes & fees
13 Jul - 14 Jul
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
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)
"Nice quiet view, able to sit on deck for hours and talk. Close to restaurants, and stores. Had a great stay."
United States
Paul M.
The price is HK$909
HK$3,341 total
includes taxes & fees
29 Jul - 30 Jul
Terra Alta - Incredible River Views and Hot Tub!
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, (47 reviews)
"Great location--easy walk to downtown Frederick. Comfortable beds, pleasant spaces and light."
United States
Alan S.
The price is HK$894
HK$2,102 total
includes taxes & fees
13 Jul - 14 Jul
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Exterior

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
9.8 out of 10, Exceptional, (206 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
The price is HK$1,137
HK$1,379 total
includes taxes & fees
14 Jul - 15 Jul
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
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, (29 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is HK$1,192
HK$3,162 total
includes taxes & fees
15 Jul - 16 Jul
New Playground•Fenced Yard•Hot Tub•King Bed•Pets
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 HK$1,686
HK$3,665 total
includes taxes & fees
11 Aug - 12 Aug
New townhouse
3 bedrooms, desk, iron/ironing board, travel cot

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, (13 reviews)
"Nice modern place with great amenities. Fenced yard was great for the pooches."
United States
John M.
The price is HK$1,192
HK$3,229 total
includes taxes & fees
13 Jul - 14 Jul
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
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 HK$935
HK$3,160 total
includes taxes & fees
19 Jul - 20 Jul
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Smart TV, fireplace

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (8 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is HK$1,202
HK$3,108 total
includes taxes & fees
19 Jul - 20 Jul
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Outdoor spa tub

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
Harpers Ferry
9.6 out of 10, Exceptional, (18 reviews)
"The house was clean and accommodating. It was truly right next door to the river riders establishment. The hot tub was AMAZING! Wish I had more time to enjoy it. We would definitely rent it again "
United States
Lynette M.
The price is HK$790
HK$2,964 total
includes taxes & fees
15 Jul - 16 Jul
Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
Interior

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Highfield-Cascade
The price is HK$868
HK$1,742 total
includes taxes & fees
20 Jul - 21 Jul
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
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 hotel is near lots of restaurants and a mall. It was close to the highway and a convenient stop in our travels."
Valerie 1-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Hagerstown, MD

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
899
Accommodation
299 Vacation Homes
Lowest Price
HK$1,379
Highest Price
HK$3,665

Explore a world of travel with Expedia