A stone tower with a flagpole and an American flag.

Boonsboro Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Boonsboro vacation rentals

A residential area with houses, roads, and green fields.

1. Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
A wooden cabin with a patio area, outdoor seating, and a fire pit.

2. 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, (19 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
The price is AED 550
AED 1,160 total
includes taxes & fees
5 Nov - 6 Nov
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A room with large windows, wooden floors, and a ceiling fan.

3. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (101 reviews)
"The cabin was clean, spacious, and"
United States
Daniel
The price is AED 826
AED 1,258 total
includes taxes & fees
5 Nov - 6 Nov
Antietam Creek - Quiet 2 Bedroom Cabin
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

4. Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Keedysville
9.8 out of 10, Exceptional, (77 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
The price is AED 518
AED 1,726 total
includes taxes & fees
19 Nov - 20 Nov
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

5. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (46 reviews)
"The house was as great! Plenty of space for 5 adults. Conveniently located to the areas we wanted to visit. Very quiet location"
United States
Melisa T.
The price is AED 375
AED 1,433 total
includes taxes & fees
18 Nov - 19 Nov
Antietam Look Out - Incredible Sunset Views!
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

6. 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, (22 reviews)
"Our stay was so enjoyable!"
United States
Kimberly C.
The price is AED 1,010
AED 1,585 total
includes taxes & fees
11 Nov - 12 Nov
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A nighttime forest path lit by string lights.

7. 1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
Sharpsburg
10.0 out of 10, Exceptional, (54 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 AED 367
AED 1,082 total
includes taxes & fees
5 Nov - 6 Nov
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
A log cabin interior with a wooden bench, a leather sofa, a coffee table, and a bookshelf.

8. 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 AED 937
AED 1,028 total
includes taxes & fees
4 Dec - 5 Dec
Cozy Downtown Cabin - Family Friendly
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

9. Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (117 reviews)
"Beautiful property! Owner is very quick to communicate and did a fantastic job making it a very relaxing place to stay!"
United States
Cindy B.
The price is AED 294
AED 755 total
includes taxes & fees
8 Nov - 9 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

10. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is AED 152
AED 361 total
includes taxes & fees
15 Nov - 16 Nov
❤️ Secluded 1940s Romantic Tiny House on the River
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (161 reviews)
"Great little spot!"
United States
Shelby W.
The price is AED 459
AED 1,071 total
includes taxes & fees
8 Nov - 9 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

12. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (56 reviews)
"Very comfortable and cozy. Our family had a great stay here."
United States
bethany c.
The price is AED 542
AED 989 total
includes taxes & fees
12 Nov - 13 Nov
Charming Cabin in the Woods with River Access
A living room with a dining table, chairs, a sofa, and a television.

13. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (26 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
The price is AED 485
AED 828 total
includes taxes & fees
9 Nov - 10 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

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

Large Family Home: 5 Mi to Dtwn Hagerstown!
3.0 star property
Williamsport
10.0 out of 10, Exceptional, (1 review)
"The place was just beautiful "
United States
Derrick
Large Family Home: 5 Mi to Dtwn Hagerstown!
A rustic, cylindrical structure with a thatched roof, a small seating area, and a view of the surrounding forest.

15. Bin There Treehouse - A Grain Bin treehouse!

Bin There Treehouse - A Grain Bin treehouse!
Washington County
9.8 out of 10, Exceptional, (6 reviews)
"Such a neat place! Very peaceful setting."
United States
Abby G.
The price is AED 532
AED 738 total
includes taxes & fees
5 Nov - 6 Nov
Bin There Treehouse - A Grain Bin treehouse!
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

16. 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)
"Property was very nice, plenty of room for our family. We would definitely recommend this house and stay there again."
United States
Charlotte S.
Large Family Home: 5 Mi to Dtwn Hagerstown!
A modern kitchen with stainless steel appliances, a dining area with a round table, and a spiral staircase leading to a living area with a sofa and a coffee table.

17. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (36 reviews)
"We enjoyed our stay here so much and when we go back to Harper’s Ferry we hope to stay in the same place again"
United States
Zachary S.
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A cozy living room with wooden walls, a flat-screen TV, a fireplace, and comfortable seating.

18. Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Harpers Ferry
9.2 out of 10, Wonderful, (57 reviews)
"Great location, with some beautiful walks through town and to the rivers."
United States
Michael
The price is AED 533
AED 886 total
includes taxes & fees
5 Nov - 6 Nov
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
A hotel entrance with a sign, a wicker chair, a wooden lattice, and a white door.

19. Best location! The Pullman Apt @ historic 1799 Inn

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (62 reviews)
"Location is unbeatable- but bring ear plugs for the train whistling through the night."
United States
Karla
The price is AED 498
AED 771 total
includes taxes & fees
8 Nov - 9 Nov
Best location! The Pullman Apt @ historic 1799 Inn
A spacious living room with a large window, a wooden coffee table, and a sofa.

20. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AED 906
AED 1,153 total
includes taxes & fees
5 Nov - 6 Nov
Schilling House
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
"Convenient location. Spacious room. Clean and comfortable. Helpful staff."
Alice 1-night trip
Posted 4 hours ago
Best Western Historic Frederick

Frequently asked questions

Can I find a vacation rental in Boonsboro?

Yes, you can find vacation rentals near well known sights in Boonsboro, or you can select a more remote option if you're looking for a relaxing stay. Boonsboro is known for its mountain views and monuments. Make sure you have time to check out the riverfront and museums during your trip.

What's the top vacation rental that Boonsboro has to offer?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This vacation home near Boonsboro is located in the mountains and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Another good choice for your trip to Boonsboro is Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit.

How many vacation rentals will I find in Boonsboro?

Expedia has 8 vacation rentals for your stay in Boonsboro.

What’s there to see and do in Boonsboro?

Crystal Grottoes Caverns and Greenbrier State Park are a couple of lovely local spots to get outside and enjoy nature. While here, South Mountain State Park and Washington Monument State Park are other places worth a visit.

What’s a vacation rental in Boonsboro like?

Vacation rentals are private properties where you can stay for short or long periods in Boonsboro. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for families.