Middletown Vacation Home Rentals from CA $346: Search Top Private Vacation Homes for Rent

Middletown Vacation Homes
Maryland
United States of America
Vacation Homes
Expedia.ca

Hotels in Middletown Vacation Rentals in Middletown Middletown Car Rentals Middletown Vacation Packages

A stone tower with a staircase leading up to it.

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

In two months

In three months

In four months

Our top choices for Middletown vacation 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 modern kitchen with stainless steel appliances, a wooden island, and a 'Welcome' sign.

A spacious living room with a sectional sofa, a coffee table, and a staircase leading to an upper level.

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

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

Middletown

10.0 out of 10, Exceptional, (159 reviews)

10/10

Exceptional

(159 reviews)

"Perfect little house in a great historic location."

Donald K.

The price is CA $135

CA $135

CA $361 total

includes taxes & fees

Oct 18 - Oct 19

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

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

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.

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

2. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly

Middletown

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

The price is CA $285

CA $285

CA $346 total

includes taxes & fees

Nov 15 - Nov 16

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 hallway with a wooden barrel, wine glasses on a rack, and a sign reading "Bourbon Street".

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

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 CA $135

CA $135

CA $361 total

includes taxes & fees

Oct 18 - Oct 19

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 cozy living room with a brown sofa, a round coffee table, and a potted plant.

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, (54 reviews)

10/10

Exceptional

(54 reviews)

"Great lodging and communicative host"

Peggy D.

The price is CA $180

CA $180

CA $442 total

includes taxes & fees

Oct 19 - Oct 20

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

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

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

A modern kitchen with grey cabinets, a white island, and a wooden stool.

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 CA $229

CA $229

CA $501 total

includes taxes & fees

Oct 27 - Oct 28

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 cozy living room with a sofa, a patterned rug, and a large window with curtains.

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

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

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, (143 reviews)

9.2/10

Wonderful

(143 reviews)

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

Jennifer W.

The price is CA $199

CA $199

CA $447 total

includes taxes & fees

Nov 15 - Nov 16

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

A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

A wooden door with a sign above it reading 'The Robin's Nest.'

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

A teal chair at a white desk with a notebook, pen, and mug.

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 CA $212

CA $212

CA $471 total

includes taxes & fees

Oct 18 - Oct 19

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

A two-story house with a front porch, a staircase, and a mailbox.

A modern kitchen with white cabinets, stainless steel appliances, a microwave, and a dishwasher.

A living room with a grey sofa set, a coffee table, a TV, and a cabinet.

A modern living room with a grey sofa, wooden side tables, and abstract wall art.

8. Dog-Friendly | Hiking| Tubing near Harpers Ferry

Dog-Friendly | Hiking| Tubing near Harpers Ferry

Brunswick

2.0 out of 10, (1 review)

2.0/10

(1 review)

"No ac just window units it was soooooo hot"

Anonymous traveller

The price is CA $178

CA $178

CA $332 total

includes taxes & fees

Oct 18 - Oct 19

Dog-Friendly | Hiking| Tubing near Harpers Ferry

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

A spacious living room with a wooden floor, a dining table with chairs, a sofa, and a TV mounted on the wall.

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

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

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, (19 reviews)

10/10

Exceptional

(19 reviews)

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

Kate M.

The price is CA $390

CA $390

CA $645 total

includes taxes & fees

Nov 2 - Nov 3

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

A brick building with a waterfall feature in front.

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

A small waterfall with lily pads, surrounded by a stone pathway and greenery.

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

10. 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.

The price is CA $252

CA $252

CA $608 total

includes taxes & fees

Oct 21 - Oct 22

New townhouse

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

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

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

11. 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 CA $302

CA $302

CA $710 total

includes taxes & fees

Oct 18 - Oct 19

Newly constructed 6 bedroom home

A hallway with wooden flooring, a staircase, a door with a white frame, a lamp on a small table, and a wall-mounted mirror.

A bedroom with a bed, a bedside table, a lamp, and a rug.

A room with a patterned armchair, a window with decorative jars, and a door leading to another room.

A dining area with a round table, four upholstered chairs, a ceiling fan, and a rug on a wooden floor.

12. Antietam House Historic Sharpsburg Retreat

Antietam House Historic Sharpsburg Retreat

Sharpsburg

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

Wonderful

(4 reviews)

"My friends and I had a wonderful time here for Labor Day! Quiet and a great location for all sorts of activities."

Nick W.

The price is CA $203

CA $203

CA $470 total

includes taxes & fees

Oct 22 - Oct 23

Antietam House Historic Sharpsburg Retreat

A deck with green chairs and a fire pit, surrounded by a house and trees.

A modern kitchen with grey cabinets, a large island with bar stools, stainless steel appliances, and pendant lighting.

A wooden dining table set with black plates, clear glasses, and a decorative vase with pink flowers.

A cozy living room with a stone fireplace, a comfortable wooden chair, and a large window.

13. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

Knoxville

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 reviews)

"Great stay, super nice people and wonderful house."

Kenzie S.

The price is CA $208

CA $208

CA $705 total

includes taxes & fees

Oct 18 - Oct 19

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

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 CA $331

CA $331

CA $425 total

includes taxes & fees

Nov 16 - Nov 17

Schilling House

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 kitchen with white cabinets, a wooden countertop, and a sliding glass door leading to an outdoor seating area.

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

15. 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, (50 reviews)

9.8/10

Exceptional

(50 reviews)

"Great location and incredibly well appointed!"

Sarah M.

The price is CA $190

CA $190

CA $410 total

includes taxes & fees

Oct 18 - Oct 19

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

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

A natural outdoor area with a grassy lawn, a fallen tree trunk, and dense foliage.

A two-story brick house with a front porch, a small garden, and a visible mailbox.

A brick house with a front porch, a small garden, and a tree in the foreground.

16. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown

Shepherdstown

The price is CA $228

CA $228

CA $444 total

includes taxes & fees

Oct 18 - Oct 19

Charming Shepherdstown Home - Walk to Downtown

A spacious kitchen with modern appliances, a dining area with a large table, and a living room with a sofa and a fireplace.

A spacious living area with a sofa, coffee table, and a dining table. There is a kitchen with modern appliances and a dining area with a view.

A wooden house with a deck, a patio with a table and chairs, and a large window overlooking a landscape.

A modern kitchen with a central island, stone backsplash, and white cabinetry.

17. Camp Patowmack - Riverfront, Hot Tub, and Sauna!

Camp Patowmack - Riverfront, Hot Tub, and Sauna!

Harpers Ferry

9.6 out of 10, Exceptional, (11 reviews)

9.6/10

Exceptional

(11 reviews)

"Great water access"

claire r.

The price is CA $263

CA $263

CA $980 total

includes taxes & fees

Nov 3 - Nov 4

Camp Patowmack - Riverfront, Hot Tub, and Sauna!

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

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

18. 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 CA $122

CA $122

CA $373 total

includes taxes & fees

Oct 21 - Oct 22

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

A wooden staircase with a handrail, a chandelier, and a patterned rug on the floor.

A porch with two wicker chairs and a white door.

A spacious living room with hardwood flooring, a fireplace, and a green sofa.

A dining room with a round table, wooden chairs, a chandelier, and a china cabinet.

19. Historic Queen Anne Family Home w Modern Comforts

Historic Queen Anne Family Home w Modern Comforts

Harpers Ferry

9.2 out of 10, Wonderful, (9 reviews)

9.2/10

Wonderful

(9 reviews)

"This was a wonderful vacation rental--clean, beautifully appointed, and located within walking distance of historic Harpers Ferry and the AT. We couldn't have asked for a nicer place to spend our long weekend getaway."

Jenny H.

The price is CA $283

CA $283

CA $578 total

includes taxes & fees

Oct 19 - Oct 20

Historic Queen Anne Family Home w Modern Comforts

An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

A garden with a wooden fence, a small wooden structure, and vibrant pink flowers.

A modern kitchen with a wooden dining table, clear chairs, and a pendant light.

A bedroom with a wooden headboard, a TV mounted on the wall, a bed with a blue floral bedspread, and a wooden floor.

20. 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, (62 reviews)

10/10

Exceptional

(62 reviews)

"Enjoyed our stay here. Host was very communicative and the place was very clean."

Delaine F.

The price is CA $212

CA $212

CA $442 total

includes taxes & fees

Oct 21 - Oct 22

Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath

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

Find vacation rentals that suit your style

Apartments

search for apartments

Villas

search for villas

Private vacation homes

search for private vacation homes

Condos

Cabins

Cottages

Chalets

Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Hotel Reviews

Red Roof Inn Leesburg, VA

10/10 Excellent

"Hola"

Juan José 1-night trip

Posted 12 hours ago

Red Roof Inn Leesburg, VA

Days Inn by Wyndham Frederick

8/10 Good

"Due to old age and limited mobility, I need to choose hotels where I can park right at the door to the room, like this Days Inn. The room was clean, the bed was comfortable, and the surroundings were very quiet. It is a budget property, so don't check in expecting luxury."

robert 1-night trip

Posted 14 hours ago

Days Inn by Wyndham Frederick