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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Boonsboro holiday homes

1. Cute Secluded Cabin with Fire Pit in Hedgesville, West Virginia

Cute Secluded Cabin with Fire Pit in Hedgesville, West Virginia
The Woods
The price is AU$394
includes taxes & fees
2 Sept - 3 Sept
Cute Secluded Cabin with Fire Pit in Hedgesville, West Virginia

2. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AU$472
includes taxes & fees
30 Aug - 31 Aug
Schilling House

3. Cozy Getaway Near History, Hiking & Adventure

Cozy Getaway Near History, Hiking & Adventure
Bolivar
10.0 out of 10, Exceptional, (1 review)
"This is a great property. Very clean and well taken care of. Backyard is fantastic too! You won’t be sorry you stayed here. Close to historic town and lots of great places to eat. Beautiful area!"
United States
Kelly
The price is AU$420
includes taxes & fees
9 Sept - 10 Sept
Cozy Getaway Near History, Hiking & Adventure

4. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
The price is AU$306
includes taxes & fees
30 Aug - 31 Aug
Cozy Downtown Cabin - Family Friendly
A two-story house with a porch, stone foundation, and a flag.

5. Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.6 out of 10, Exceptional, (210 reviews)
"Great place, pet friendly. "
United States
Doug P.
The price is AU$247
includes taxes & fees
21 Sept - 22 Sept
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
A nighttime forest path lit by string lights.

6. 5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Sharpsburg
10.0 out of 10, Exceptional, (50 reviews)
"The house was in a great location with the winery and battlefield nearby, and the house was very nice and comfortable."
United States
Nancy D.
The price is AU$352
includes taxes & fees
1 Sept - 2 Sept
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ 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.

7. Antietam House Historic Sharpsburg Retreat

Antietam House Historic Sharpsburg Retreat
Sharpsburg
8.8 out of 10, Excellent, (3 reviews)
"The house is a perfect spot for walking to the battlefield"
United States
Karen
Antietam House Historic Sharpsburg Retreat
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (154 reviews)
"An absolutely charming getaway spot tucked in a small town with trendy shops and eateries. Our host gave fabulous recommendations and the property was spotless, cozy and well equipped for the perfect weekend getaway."
United States
Jennifer P.
The price is AU$491
includes taxes & fees
1 Sept - 2 Sept
Charming "Cream of the Crop" Cape ~❤️of Middletown
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

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, (16 reviews)
"Great location for the Spring Festival. The beds were very comfortable. Kitchen was well equipped ."
United States
Renee W.
The price is AU$616
includes taxes & fees
1 Sept - 2 Sept
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

10. 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 AU$622
includes taxes & fees
3 Sept - 4 Sept
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

11. 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, (72 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is AU$432
includes taxes & fees
30 Aug - 31 Aug
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A riverside property with a wooden deck overlooking a river, surrounded by trees and a clear sky.

12. 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 AU$776
includes taxes & fees
9 Sept - 10 Sept
Exclusive Wooded Chalet w Magnificent River Views
A deck with green chairs and a fire pit, surrounded by a house and trees.

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, (25 reviews)
"Easy to get in, instructions and expectations were clear, amenities were as expected, and the home was beautiful. "
United States
Katherine Z.
The price is AU$694
includes taxes & fees
27 Aug - 28 Aug
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A covered outdoor patio with a table and chairs, a wooden deck, and a view of greenery.

14. Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (23 reviews)
"We really enjoyed our recent stay. Check-in was simple, the host very responsive, location is excellent (we walked everywhere) and well designed. Would stay again."
United States
Richard M.
The price is AU$395
includes taxes & fees
7 Sept - 8 Sept
Chic, pets, walk to downtown
A patio area with a wooden table, chairs, a decorative vase, and a fire pit.

15. 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, (51 reviews)
"Great lodging and communicative host"
United States
Peggy D.
The price is AU$368
includes taxes & fees
31 Aug - 1 Sept
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A park with a pond, a bridge, and a church in the background.

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (134 reviews)
"The place was so fun and close to the bars! The rooms where cleans "
United States
Anonymous traveller
The price is AU$405
includes taxes & fees
30 Aug - 31 Aug
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A modern kitchen with grey cabinets, a central island, and pendant lighting.

17. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (97 reviews)
"The host and property was everything we needed."
United States
Christopher D.
The price is AU$488
includes taxes & fees
31 Aug - 1 Sept
Luxury Condo In Downtown Frederick
A living room with a stone fireplace, a gray sofa with patterned cushions, and wooden flooring.

18. Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (111 reviews)
"Wonderful place to stay. Comfotable beds and big enough for a large crowd. The property owners are incredibly kind and responsive. Our family loved our stay. "
United States
Jenn C.
The price is AU$853
includes taxes & fees
31 Aug - 1 Sept
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

19. 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, (43 reviews)
"Great place to stay for the weekend."
United States
Bea G.
The price is AU$477
includes taxes & fees
30 Aug - 31 Aug
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

20. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (20 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 AU$695
includes taxes & fees
30 Aug - 31 Aug
Newly constructed 6 bedroom home
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

Fairfield Inn & Suites by Marriott Frederick

Fairfield Inn & Suites by Marriott Frederick

10/10 Excellent
"Very welcoming, room was very clean and spacious!"
Ruby 1-night trip
Posted 1 hour ago
Fairfield Inn & Suites by Marriott Frederick

Find out more about Boonsboro

Boonsboro Holiday Homes information

Number of reviews
1,093
Accommodation
288 Holiday Homes
Lowest Price
AU$247
Highest Price
AU$853