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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Boonsboro holiday homes

A teepee with a sleeping area and a hot tub.

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 €294
includes taxes & fees
4 Oct - 5 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

2. 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)
"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 €226
includes taxes & fees
4 Oct - 5 Oct
Charming "Cream of the Crop" Cape ~❤️of Middletown
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

3. 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 €412
includes taxes & fees
6 Oct - 7 Oct
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
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, (18 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
The price is €399
includes taxes & fees
8 Oct - 9 Oct
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A bedroom with a bed, a dresser, a ceiling fan, and a window with blinds.

5. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 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!"
United States
Laura K.
The price is €214
includes taxes & fees
1 Nov - 2 Nov
Cozy Downtown Cabin - Family Friendly
A house with a deck, outdoor seating, and a fire pit.

6. 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 €643
includes taxes & fees
14 Oct - 15 Oct
Exclusive Wooded Chalet w Magnificent River Views
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

7. 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 €229
includes taxes & fees
4 Oct - 5 Oct
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A window with a view of a grassy yard and trees.

8. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
Charming Shepherdstown Home - Walk to Downtown
A patio area with a wooden table, chairs, a decorative vase, and a fire pit.

9. 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)
"Great lodging and communicative host"
United States
Peggy D.
The price is €269
includes taxes & fees
5 Oct - 6 Oct
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
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 €432
includes taxes & fees
4 Oct - 5 Oct
Newly constructed 6 bedroom home
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

11. Schilling House

Schilling House
3.0 star property
Bolivar
The price is €303
includes taxes & fees
4 Oct - 5 Oct
Schilling House
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

12. 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)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is €279
includes taxes & fees
1 Nov - 2 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A modern kitchen with grey cabinets, a central island, and pendant lighting.

13. 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 €310
includes taxes & fees
6 Oct - 7 Oct
Luxury Condo In Downtown Frederick
A house with a well-lit entrance, a small garden, and a gravel driveway.

14. 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 €232
includes taxes & fees
7 Oct - 8 Oct
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
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.

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 €329
includes taxes & fees
5 Oct - 6 Oct
New, Contemporary House in Historic Harpers Ferry
A modern kitchen with a large island, white cabinets, and a dining area with a bench and chairs.

16. 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)
"Had a fantastic time and everything was great! Highly recommend this spot for a vacation if you’re headed for Harper’s ferry."
United States
James A.
The price is €422
includes taxes & fees
8 Oct - 9 Oct
Riverview Retreat - Pool, Hot Tub, and Mtn Views!
A bedroom with a large bed, a bench, a chair, a nightstand, and a wall with decorative plates.

17. Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (21 reviews)
"Overall good property- close location to all attractions"
United States
Trisha P.
The price is €379
includes taxes & fees
6 Oct - 7 Oct
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

18. 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)
"Great location and incredibly well appointed!"
United States
Sarah M.
The price is €263
includes taxes & fees
8 Oct - 9 Oct
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A living room with two dark sofas, a wooden coffee table, and a chandelier.

19. Cozy Getaway Near History, Hiking & Adventure

Cozy Getaway Near History, Hiking & Adventure
Bolivar
10.0 out of 10, Exceptional, (2 reviews)
"This house was perfect for our getaway. Clean and comfortable. Close to everything."
United States
Ashlee O.
The price is €387
includes taxes & fees
8 Oct - 9 Oct
Cozy Getaway Near History, Hiking & Adventure
An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

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)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is €273
includes taxes & fees
13 Oct - 14 Oct
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.
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Top Boonsboro Hotel Reviews

Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

10/10 Excellent
"Stayed here one night for a biz trip and was very pleased with the experience!! Quiet, clean, and a very comfortable bed. Tons of outlets available which was great because I had to tech check some gear and charge a bunch of batteries. They had a breakfast area but we did not have anything. Looked nice though. Historic downtown Harpers Ferry is a 4 min drive. We were able to spend 1.5hrs walking around and taking in some scenery. Beautiful town with lots of stores that were actually open on a Tuesday midday. Looking forward to visiting in the future with my family. Will definitely stay at this hotel again!!"
Benjamin 1-night trip
Posted less than an hour ago
Quality Inn Harpers Ferry - Charles Town

Find out more about Boonsboro

Boonsboro Holiday Homes information

Number of reviews
768
Accommodation
291 Holiday Homes
Lowest Price
€214
Highest Price
€643