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Our top choices for Middletown holiday homes

A two-story house with a front porch, a chimney, and a small garden with pumpkins.

A porch with a stone wall, a red door, an American flag, a chair with a cushion, and a 'STAY' sign.

A spacious living room with a high ceiling, a staircase, a large window with a view, and a cozy fireplace area.

A modern kitchen with stainless steel appliances, a wooden island, and a 'Welcome' sign.

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)

10/10

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!"

Adair M.

The price is £184

£184

includes taxes & fees

5 Oct - 6 Oct

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

A bedroom with a bed, a dresser, a ceiling fan, and a window with blinds.

A log cabin interior with a wooden bench, a leather sofa, a coffee table, and a bookshelf.

A covered outdoor seating area with a sofa and a table, a sign with 'hello SPRING', and a view of a garden.

A living room with a brick fireplace, a rocking chair, a patterned sofa, and a large rug.

2. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly

Middletown

10.0 out of 10, Exceptional, (1 review)

10/10

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!"

Laura K.

The price is £175

£175

includes taxes & fees

1 Nov - 2 Nov

Cozy Downtown Cabin - Family Friendly

A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

A staircase with white railings and wooden steps, leading to a door with a wreath and a framed picture on the wall.

A dining area with a wooden table, two chairs, a vase with flowers, and a hanging light fixture.

A living room with a fireplace, a television, a staircase, and a bookshelf.

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, (74 reviews)

10/10

Exceptional

(74 reviews)

"Lovely home. Great location! Host was amazingly helpful!"

Tory D.

The price is £219

£219

includes taxes & fees

13 Oct - 14 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.

A canal with boats, a bridge, and a building with flags.

A bedroom with a bed, a ceiling fan, a window, and a television.

A cozy living room with a brown leather sofa, a round coffee table, and a blue accent wall with woven wall art.

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)

10/10

Exceptional

(52 reviews)

"Great lodging and communicative host"

Peggy D.

The price is £222

£222

includes taxes & fees

5 Oct - 6 Oct

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

A modern kitchen with grey cabinets, a central island, and pendant lighting.

A bedroom with a bed, a bench, a desk, and two windows.

A spacious living room with a grey sofa, a coffee table, and a patterned rug.

A hallway with brick walls, a white door, and a black console table with a vase.

5. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick

Downtown Frederick

9.2 out of 10, Wonderful, (98 reviews)

9.2/10

Wonderful

(98 reviews)

"Very clean, had everything we needed and close to shopping and restaurants. "

Kathy S.

The price is £261

£261

includes taxes & fees

6 Oct - 7 Oct

Luxury Condo In Downtown Frederick

A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

A backyard patio with a table and chairs, surrounded by a wooden fence and various plants.

A living room with a fireplace, a television, and a large window with curtains.

A bedroom with a bed, dresser, mirror, and bedside table.

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

9.2 out of 10, Wonderful, (141 reviews)

9.2/10

Wonderful

(141 reviews)

"Very old but lovely building. Great parking and patio."

Jennifer W.

The price is £238

£238

includes taxes & fees

1 Nov - 2 Nov

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

A room with a white desk, shelves with patterned fabric, a blue chair, and a patterned carpet.

A kitchen with a brick wall, a sign for customer service, a microwave, and a coffee machine.

A gravel driveway leading to a house with a brick exterior and a wooden deck.

A cozy attic bedroom with a skylight, a wicker chair, a round table, and a bed with a headboard.

7. 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)

9.8/10

Exceptional

(18 reviews)

"Extremely cute and a wonderful place to relax."

A D.

The price is £250

£250

includes taxes & fees

5 Oct - 6 Oct

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

A brick building with a waterfall feature in front.

A modern kitchen with dark cabinets, a central island, and a dining area with a white table and chairs.

A modern kitchen with dark wood cabinets, stainless steel appliances, and a central island.

A modern kitchen with a granite countertop, stainless steel appliances, and a white backsplash.

8. New townhouse

New townhouse

Frederick

9.6 out of 10, Exceptional, (12 reviews)

9.6/10

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. "

Tereasa G.

New townhouse

A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

A two-story house with a green exterior, a red door, and a porch with steps leading to the front door.

A living room with a fireplace, a television, and a dining area with a table and chairs.

A spacious living room with hardwood flooring, two dark armchairs, a round ottoman, a floor lamp, and large windows with white curtains.

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)

10/10

Exceptional

(18 reviews)

"Beautiful house in a bucolic setting. Perfect for a family for the night."

Kate M.

The price is £342

£342

includes taxes & fees

19 Oct - 20 Oct

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

A modern bathroom with a bathtub, a towel rack, and a mirror.

A modern dining area with a glass table and two black metal stools. A framed floral artwork hangs on the wall above the table.

10. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home

Frederick

10.0 out of 10, Exceptional, (22 reviews)

10/10

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!"

Janice M.

The price is £365

£365

includes taxes & fees

11 Oct - 12 Oct

Newly constructed 6 bedroom home

A house with a well-lit entrance, a small garden, and a gravel driveway.

A modern kitchen with stainless steel appliances, a window with a view of trees, and a blue countertop.

A dark entrance with a lit door, two windows on either side, and a bell on the right.

A dining area with a table set for two, a clock on the wall, and a blue door with a window.

11. 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)

9.8/10

Exceptional

(24 reviews)

"Nice place to stay. Could use some privacy."

Arnold A.

The price is £193

£193

includes taxes & fees

5 Oct - 6 Oct

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

A single-story building with a gabled roof, a front porch, and a small deck area.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

A modern kitchen with a dishwasher, a coffee maker, and a microwave. There is a window with a curtain, and a sofa is visible in the adjacent living area.

A living room with a blue sofa, a grey armchair, and a large window with curtains.

12. New, Contemporary House in Historic Harpers Ferry

New, Contemporary House in Historic Harpers Ferry

Harpers Ferry

9.6 out of 10, Exceptional, (8 reviews)

9.6/10

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. "

Erin J.

The price is £281

£281

includes taxes & fees

5 Oct - 6 Oct

New, Contemporary House in Historic Harpers Ferry

An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

A dining area with a wooden table and clear chairs, a kitchen with shelves above the counter, and a view through a door to the outside.

A modern living room with a large flat-screen TV mounted on the wall, a sofa, a coffee table, and a side table with a lamp.

A modern living room with a white sofa, a wooden coffee table, and a large grey door.

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)

9.8/10

Exceptional

(48 reviews)

"Great location and incredibly well appointed!"

Sarah M.

The price is £224

£224

includes taxes & fees

8 Oct - 9 Oct

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

A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

A spacious living room with a large window, a wooden coffee table, and a sofa.

A kitchen with white cabinets, a black refrigerator, a wooden table, and a ceiling fan.

A bathroom with a toilet, sink, and shower curtain.

14. Schilling House

Schilling House

3.0 star property

Bolivar

The price is £250

£250

includes taxes & fees

12 Oct - 13 Oct

Schilling House

A bathroom with a towel rack, a mirror, a sink, and a potted plant.

A living room with a sofa, a wooden coffee table, a patterned rug, and a radiator.

A fireplace with a TV above it, a patterned rug, and a wooden bench.

A white house with a dark roof, a front porch, and a circular garden with three pig statues.

15. 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, (6 reviews)

10/10

Exceptional

(6 reviews)

The price is £173

£173

includes taxes & fees

19 Oct - 20 Oct

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

A window with a view of a grassy yard and trees.

A kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.

A two-story brick house with a front porch, a small front yard, and a sidewalk leading to the entrance.

A covered outdoor area with a brick wall, a metal railing, and a wicker chair with a red cushion.

16. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown

Shepherdstown

The price is £232

£232

includes taxes & fees

14 Oct - 15 Oct

Charming Shepherdstown Home - Walk to Downtown

KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

DINING ROOM - 2nd floor dining room easily fits 6, spare chairs, stairs backyard

LIVING ROOM - 2nd floor, sitting area, bar area to eat at while looking outside.

ENTRANCE - front walk made of brick, lovely landscaping. Keyless entry.

17. 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)

8.2/10

Very good

(66 reviews)

"Lovely place along the c&o. The host was very accommodating and helpful."

Laura D.

The price is £349

£349

includes taxes & fees

5 Oct - 6 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.

An outdoor deck with a grill, seating, and a staircase leading to an upper level.

A spacious living room with a blue sofa, a coffee table, and a bookshelf. There is a door with an American flag, a wall with a mountain design, and a kitchen area with a microwave.

A modern kitchen with a large island, wooden accents, and pendant lighting.

18. 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)

10/10

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."

James A.

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

A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

A cozy living room with a fireplace, wooden furniture, and a dining area with a table and chairs.

A stone building with a covered porch, columns, and a lattice fence.

A cozy living room with a staircase, a fireplace, a bookshelf, and a door leading to another room.

19. 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)

9.0/10

Wonderful

(8 reviews)

"Lovely! Our host was gracious and helpful. Property was ideal for our family getaway. i’m"

Mary F.

The price is £335

£335

includes taxes & fees

14 Oct - 15 Oct

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

A hot tub in a forested area with a rocky ground and trees.

A living room with a blue sofa, a coffee table, and artwork on the wall.

A bedroom with a bed, a ceiling fan, two windows, a nightstand, a lamp, and a painting.

A modern kitchen with white cabinets, a stainless steel refrigerator, and an oven.

20. The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub

Harpers Ferry

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "

Brett D.

The price is £277

£277

includes taxes & fees

7 Oct - 8 Oct

The Blue Jay | New House in the Woods w/ Hot Tub

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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