A stone tower with a flagpole and an American flag.

Holiday Homes in Boonsboro

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Check prices for these dates

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

Our top choices for Boonsboro holiday homes

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

1. 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 NZ$590
includes taxes & fees
15 Oct - 16 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A hallway with wooden flooring, a staircase, a door with a white frame, a lamp on a small table, and a wall-mounted mirror.

2. 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 NZ$654
includes taxes & fees
22 Oct - 23 Oct
Antietam House Historic Sharpsburg Retreat
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

3. 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)
"Perfect little house in a great historic location."
United States
Donald K.
The price is NZ$560
includes taxes & fees
19 Oct - 20 Oct
Charming "Cream of the Crop" Cape ~❤️of Middletown
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

4. 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 NZ$788
includes taxes & fees
20 Oct - 21 Oct
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

5. 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 NZ$793
includes taxes & fees
19 Oct - 20 Oct
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A bedroom with a bed, a dresser, a ceiling fan, and a window with blinds.

6. 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 NZ$451
includes taxes & fees
18 Oct - 19 Oct
Cozy Downtown Cabin - Family Friendly
A house with a deck, outdoor seating, and a fire pit.

7. Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (20 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
The price is NZ$1,522
includes taxes & fees
29 Oct - 30 Oct
Exclusive Wooded Chalet w Magnificent River Views
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

8. Large Family Home: 5 Mi to Dtwn Hagerstown!

Large Family Home: 5 Mi to Dtwn Hagerstown!
Williamsport
8.8 out of 10, Excellent, (21 reviews)
The price is NZ$788
includes taxes & fees
20 Oct - 21 Oct
Large Family Home: 5 Mi to Dtwn Hagerstown!
A kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.

9. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is NZ$552
includes taxes & fees
15 Oct - 16 Oct
Charming Shepherdstown Home - Walk to Downtown
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

10. 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 NZ$556
includes taxes & fees
18 Oct - 19 Oct
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A deck with green chairs and a fire pit, surrounded by a house and trees.

11. 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 NZ$880
includes taxes & fees
18 Oct - 19 Oct
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A two-story house with a front porch, a staircase, and a mailbox.

12. 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 NZ$415
includes taxes & fees
18 Oct - 19 Oct
Dog-Friendly | Hiking| Tubing near Harpers Ferry
A kitchen with a countertop, a kettle, a coffee maker, a microwave, and wall-mounted shelves with decorative items.

13. 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 NZ$654
includes taxes & fees
22 Oct - 23 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.

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, (50 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
The price is NZ$511
includes taxes & fees
18 Oct - 19 Oct
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A house with a well-lit entrance, a small garden, and a gravel driveway.

15. 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 NZ$450
includes taxes & fees
26 Oct - 27 Oct
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.

16. 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 NZ$701
includes taxes & fees
9 Nov - 10 Nov
Historic Queen Anne Family Home w Modern Comforts
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, (8 reviews)
The price is NZ$394
includes taxes & fees
19 Oct - 20 Oct
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

18. 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)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is NZ$539
includes taxes & fees
21 Oct - 22 Oct
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

19. 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, (15 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is NZ$829
includes taxes & fees
9 Nov - 10 Nov
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
A brick building with a waterfall feature in front.

20. 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 NZ$788
includes taxes & fees
11 Nov - 12 Nov
New townhouse
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 Boonsboro Hotel Reviews

Best Western Historic Frederick

Best Western Historic Frederick

10/10 Excellent
"Overall a nice place with a great staff. I had a late checkout and the room was a little noisy in the morning (I could hear the cleaning staff and the room next to mine getting ready to leave) but it wasn’t too bad."
David 1-night trip
Posted 3 hours ago
Best Western Historic Frederick

Find out more about Boonsboro

Boonsboro Holiday Homes information

Number of reviews
603
Accommodation
291 Holiday Homes
Lowest Price
NZ$394
Highest Price
NZ$1,522