A stone tower with a flagpole and an American flag.

Boonsboro Vacation Rentals

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Our top choices for Boonsboro vacation rentals

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (82 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is CA $100
CA $196 total
includes taxes & fees
Aug 31 - Sep 1
❤️ Secluded 1940s Romantic Tiny House on the River

2. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (96 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
The price is CA $278
CA $457 total
includes taxes & fees
Aug 20 - Aug 21
Antietam Creek - Quiet 2 Bedroom Cabin

3. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
The price is CA $154
CA $518 total
includes taxes & fees
Sep 1 - Sep 2
Antietam Look Out - Incredible Sunset Views!

4. 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 CA $201
CA $243 total
includes taxes & fees
Aug 22 - Aug 23
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

5. 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, (72 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 CA $150
CA $521 total
includes taxes & fees
Aug 24 - Aug 25
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

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, (16 reviews)
"Beautiful historic home. Hosts were very welcoming and the place was newly renovated. "
United States
Drew M.
The price is CA $382
CA $625 total
includes taxes & fees
Aug 24 - Aug 25
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

7. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (35 reviews)
"Great location, clean place. "
United States
Warren B.
The price is CA $93
CA $277 total
includes taxes & fees
Sep 2 - Sep 3
Cozy, dog-friendly, downtown

8. Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (9 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
The price is CA $111
CA $299 total
includes taxes & fees
Sep 7 - Sep 8
Pet-friendly, heart of downtown

9. Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (11 reviews)
"Great location for a peaceful solo night away -- thanks!"
United States
Kristina S.
The price is CA $128
CA $318 total
includes taxes & fees
Aug 31 - Sep 1
Huge 1br apt, baby-friendly, dogs, walkable downtown

10. Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
Blue Ridge Summit
9.6 out of 10, Exceptional, (19 reviews)
"Location and amenities"
United States
Shane B.
The price is CA $104
CA $260 total
includes taxes & fees
Aug 25 - Aug 26
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

11. 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 CA $187
CA $419 total
includes taxes & fees
Aug 22 - Aug 23
Charming "Cream of the Crop" Cape ~❤️of Middletown

12. 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
8.4 out of 10, Very good, (63 reviews)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
The price is CA $286
CA $638 total
includes taxes & fees
Sep 3 - Sep 4
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

13. Antietam House Historic Sharpsburg Retreat

Antietam House Historic Sharpsburg Retreat
Sharpsburg
9.0 out of 10, Wonderful, (2 reviews)
"The house is a perfect spot for walking to the battlefield"
United States
Karen
The price is CA $267
CA $541 total
includes taxes & fees
Aug 18 - Aug 19
Antietam House Historic Sharpsburg Retreat

14. Downtown Frederick retreat with parking. Dog- and baby-friendly!

Downtown Frederick retreat with parking. Dog- and baby-friendly!
Frederick
9.8 out of 10, Exceptional, (7 reviews)
"My daughter and I stayed here when we came down to visit friends. The place was so clean and cozy. For us the weather wasn’t good, so we weren’t able to walk to the downtown area, but it is so close and was nice to see. We would definitely stay here again! "
United States
Kelley R.
The price is CA $132
CA $377 total
includes taxes & fees
Aug 31 - Sep 1
Downtown Frederick retreat with parking. Dog- and baby-friendly!

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 CA $119
CA $361 total
includes taxes & fees
Aug 18 - Aug 19
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

16. 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 CA $472
CA $807 total
includes taxes & fees
Sep 9 - Sep 10
Exclusive Wooded Chalet w Magnificent River Views

17. Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (23 reviews)
"Relaxing, close to all."
United States
Valarie
The price is CA $142
CA $508 total
includes taxes & fees
Sep 3 - Sep 4
Peregrine's Perch - Cabin Overlooking the River!

18. 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
9.8 out of 10, Exceptional, (70 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is CA $215
CA $447 total
includes taxes & fees
Aug 24 - Aug 25
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

19. 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)
"We had a wonderful Mother’s Day weekend visiting our daughter and her family! The home was exactly as pictured, very clean and a great location! We could easily walk to our daughter’s house and anything in downtown Frederick. Would definitely stay here agin! "
United States
Dawn W.
The price is CA $169
CA $384 total
includes taxes & fees
Sep 8 - Sep 9
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

20. Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
The price is CA $139
CA $474 total
includes taxes & fees
Aug 20 - Aug 21
Cabin at the Gap | You Won't Believe the View!
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

Find out more about Boonsboro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Boonsboro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct: This vacation home rental near Boonsboro offers a patio, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Boonsboro?

Expedia has 6 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.