A stone tower with a staircase leading up to it.

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Middletown vacation 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, (158 reviews)
"Perfect little house in a great historic location."
United States
Donald K.
The price is CA $207
CA $449 total
includes taxes & fees
Oct 19 - Oct 20
Charming "Cream of the Crop" Cape ~❤️of Middletown
A bedroom with a bed, a dresser, a ceiling fan, and a window with blinds.

2. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is CA $302
CA $366 total
includes taxes & fees
Oct 26 - Oct 27
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, (74 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is CA $207
CA $449 total
includes taxes & fees
Oct 19 - Oct 20
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A modern kitchen with grey cabinets, a central island, and pendant lighting.

4. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (98 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is CA $228
CA $502 total
includes taxes & fees
Oct 28 - Oct 29
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.

5. 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, (142 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is CA $200
CA $449 total
includes taxes & fees
Nov 8 - Nov 9
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.

6. 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)
"Extremely cute and a wonderful place to relax."
United States
A D.
The price is CA $213
CA $476 total
includes taxes & fees
Nov 8 - Nov 9
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A brick building with a waterfall feature in front.

7. New townhouse

New townhouse
Frederick
9.6 out of 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. "
United States
Tereasa G.
The price is CA $258
CA $616 total
includes taxes & fees
Oct 20 - Oct 21
New townhouse
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

8. 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)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
The price is CA $392
CA $648 total
includes taxes & fees
Oct 19 - Oct 20
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A two-story house with a front porch, a staircase, and a mailbox.

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

Dog-Friendly | Hiking| Tubing near Harpers Ferry
Brunswick
2.0 out of 10, (1 review)
"No ac just window units it was soooooo hot"
United States
Anonymous traveller
The price is CA $179
CA $338 total
includes taxes & fees
Oct 19 - Oct 20
Dog-Friendly | Hiking| Tubing near Harpers Ferry
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, (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!"
United States
Janice M.
The price is CA $304
CA $713 total
includes taxes & fees
Oct 19 - Oct 20
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.

11. Antietam House Historic Sharpsburg Retreat

Antietam House Historic Sharpsburg Retreat
Sharpsburg
9.0 out of 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."
United States
Nick W.
The price is CA $204
CA $471 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.

12. 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)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is CA $209
CA $717 total
includes taxes & fees
Oct 19 - Oct 20
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A deck with outdoor seating and a lake view.

13. 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
10.0 out of 10, Exceptional, (12 reviews)
"Had a wonderful stay here. Shaun was an excellent host with easy communication. Peaceful location with a lake! Convenient to Harper’s Ferry. "
United States
Liz P.
The price is CA $57
CA $354 total
includes taxes & fees
Oct 22 - Oct 23
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

14. 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, (49 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
The price is CA $191
CA $412 total
includes taxes & fees
Oct 18 - Oct 19
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A kitchen with a countertop, a kettle, a coffee maker, a microwave, and wall-mounted shelves with decorative items.

15. New, Contemporary House in Historic Harpers Ferry

New, Contemporary House in Historic Harpers Ferry
Harpers Ferry
9.6 out of 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. "
United States
Erin J.
The price is CA $150
CA $539 total
includes taxes & fees
Oct 22 - Oct 23
New, Contemporary House in Historic Harpers Ferry
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

16. Schilling House

Schilling House
3.0 star property
Bolivar
The price is CA $364
CA $461 total
includes taxes & fees
Oct 29 - Oct 30
Schilling House
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

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)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
The price is CA $294
CA $657 total
includes taxes & fees
Oct 19 - Oct 20
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.

18. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is CA $229
CA $443 total
includes taxes & fees
Oct 14 - Oct 15
Charming Shepherdstown Home - Walk to Downtown
A wooden staircase with a handrail, a chandelier, and a patterned rug on the floor.

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)
"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."
United States
Jenny H.
The price is CA $277
CA $567 total
includes taxes & fees
Nov 9 - Nov 10
Historic Queen Anne Family Home w Modern Comforts
A house with a well-lit entrance, a small garden, and a gravel driveway.

20. 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)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is CA $122
CA $372 total
includes taxes & fees
Oct 26 - Oct 27
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
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

Best Western Historic Frederick

Best Western Historic Frederick

8/10 Good
"The room was clean and the area is quiet for a nights sleep. Breakfast needed some love but enough there to get you going"
Dominic 1-night trip
Posted 11 hours ago
Best Western Historic Frederick

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
727
Accommodation
278 Vacation Homes
Lowest Price
CA $354
Highest Price
CA $717

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