A stone tower with a staircase leading up to it.

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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, (154 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 HK$666
HK$1,903 total
includes taxes & fees
2 Sept - 3 Sept
Charming "Cream of the Crop" Cape ~❤️of Middletown

2. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
The price is HK$1,411
HK$1,712 total
includes taxes & fees
1 Sept - 2 Sept
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, (72 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is HK$666
HK$1,903 total
includes taxes & fees
1 Sept - 2 Sept
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, (51 reviews)
"Great lodging and communicative host"
United States
Peggy D.
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A covered outdoor patio with a table and chairs, a wooden deck, and a view of greenery.

5. Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (23 reviews)
"We really enjoyed our recent stay. Check-in was simple, the host very responsive, location is excellent (we walked everywhere) and well designed. Would stay again."
United States
Richard M.
The price is HK$811
HK$2,173 total
includes taxes & fees
7 Sept - 8 Sept
Chic, pets, walk to downtown
A modern kitchen with grey cabinets, a central island, and pendant lighting.

6. 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 HK$1,235
HK$2,730 total
includes taxes & fees
2 Sept - 3 Sept
Luxury Condo In Downtown Frederick
A park with a pond, a bridge, and a church in the background.

7. 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, (136 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is HK$957
HK$2,302 total
includes taxes & fees
1 Sept - 2 Sept
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A nighttime forest path lit by string lights.

8. 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, (50 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$784
HK$2,242 total
includes taxes & fees
1 Sept - 2 Sept
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
A two-story house with a porch, stone foundation, and a flag.

9. 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, (210 reviews)
"Great place, pet friendly. "
United States
Doug P.
The price is HK$1,137
HK$1,371 total
includes taxes & fees
7 Sept - 8 Sept
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

10. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (20 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$1,670
HK$3,923 total
includes taxes & fees
1 Sept - 2 Sept
Newly constructed 6 bedroom home
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

11. 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)
"Great location for the Spring Festival. The beds were very comfortable. Kitchen was well equipped ."
United States
Renee W.
The price is HK$2,156
HK$3,565 total
includes taxes & fees
7 Sept - 8 Sept
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A brick building with a waterfall feature in front.

12. 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$1,849
HK$3,904 total
includes taxes & fees
2 Sept - 3 Sept
New townhouse
A spacious kitchen with modern appliances, a dining area with a large table, and a living room with a sofa and a fireplace.

13. 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.
The price is HK$902
HK$4,621 total
includes taxes & fees
9 Sept - 10 Sept
Camp Patowmack - Riverfront, Hot Tub, and Sauna!

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 HK$1,482
HK$3,457 total
includes taxes & fees
2 Sept - 3 Sept
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A two-story house with a porch, green shutters, and a red roof.

15. 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 HK$1,393
HK$2,700 total
includes taxes & fees
1 Sept - 2 Sept
Enchanting Cottage, walk to Downtown Harpers Ferry
An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

16. 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, (58 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is HK$1,090
HK$2,306 total
includes taxes & fees
1 Sept - 2 Sept
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
A bathroom with a towel rack, a mirror, a sink, and a potted plant.

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

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Highfield-Cascade
10.0 out of 10, Exceptional, (4 reviews)
"The house was adorable, the personalized touches, snack basket and welcome note were awesome and made our day. The host was very nice and welcoming. We had a wonderful time."
United States
Bill C.
The price is HK$917
HK$1,828 total
includes taxes & fees
2 Sept - 3 Sept
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

18. Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Harpers Ferry
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is HK$1,490
HK$3,494 total
includes taxes & fees
1 Sept - 2 Sept
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
A two-story house with a porch and a chimney.

19. Schilling House

Schilling House
3.0 star property
Bolivar
The price is HK$2,148
HK$2,691 total
includes taxes & fees
1 Sept - 2 Sept
Schilling House
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.

20. New, Contemporary House in Historic Harpers Ferry

New, Contemporary House in Historic Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (7 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$784
HK$2,908 total
includes taxes & fees
1 Sept - 2 Sept
New, Contemporary House in Historic Harpers Ferry
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

Comfort Suites Hagerstown Southeast

Comfort Suites Hagerstown Southeast

10/10 Excellent
"Very good and clean olsce"
christopher 1-night trip
Posted 3 hours ago
Comfort Suites Hagerstown Southeast

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
916
Accommodation
279 Vacation Homes
Lowest Price
HK$1,371
Highest Price
HK$4,621

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