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. Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
The price is CA $361
CA $424 total
includes taxes & fees
Sep 14 - Sep 15
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland

2. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (97 reviews)
"We had a great stay! Everything was clean & well organized. The house was well stocked with everything we need. We would definitely stay here again."
United States
Stephen V.
The price is CA $276
CA $461 total
includes taxes & fees
Sep 7 - Sep 8
Antietam Creek - Quiet 2 Bedroom Cabin

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (83 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is CA $61
CA $152 total
includes taxes & fees
Oct 5 - Oct 6
❤️ Secluded 1940s Romantic Tiny House on the River

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, (75 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 $154
CA $535 total
includes taxes & fees
Sep 14 - Sep 15
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

5. 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)
"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 CA $249
CA $494 total
includes taxes & fees
Sep 27 - Sep 28
Charming "Cream of the Crop" Cape ~❤️of Middletown

6. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (44 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
The price is CA $163
CA $531 total
includes taxes & fees
Sep 22 - Sep 23
Antietam Look Out - Incredible Sunset Views!

7. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (24 reviews)
"Host let us in a bit early which was nice!"
United States
John
The price is CA $166
CA $303 total
includes taxes & fees
Sep 6 - Sep 7
Quaint Mini Cottage in Shepherdstown - Walking Distance

8. 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 CA $381
CA $629 total
includes taxes & fees
Sep 13 - Sep 14
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

9. 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 CA $265
CA $616 total
includes taxes & fees
Sep 15 - Sep 16
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

10. Bin There Treehouse - A Grain Bin treehouse!

Bin There Treehouse - A Grain Bin treehouse!
Washington County
10.0 out of 10, Exceptional, (4 reviews)
"This place was amazing! Every little detail was thought of, and makes for just an incredible, delightful stay. Has all the amenities of what you’d expect in a home, yet has the unique appeal of a fantastic little treehouse!!"
United States
Whiskey Dent G.
The price is CA $223
CA $318 total
includes taxes & fees
Sep 8 - Sep 9
Bin There Treehouse - A Grain Bin treehouse!

11. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (53 reviews)
"Loved the place and area."
United States
Steve R.
The price is CA $265
CA $469 total
includes taxes & fees
Sep 10 - Sep 11
Charming Cabin in the Woods with River Access

12. 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 CA $138
CA $361 total
includes taxes & fees
Sep 7 - Sep 8
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

13. Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (67 reviews)
"Cute downtown area with multiple spots to grab breakfast and convenience store stuff. Easy access to Harper's Ferry and made for a nice restful spot between hikes in nature and around town."
United States
Robert
The price is CA $137
CA $247 total
includes taxes & fees
Sep 18 - Sep 19
Cozy Getaway near Harper`s Ferry, C&O & Potomac

14. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean place. "
United States
Warren B.
The price is CA $123
CA $315 total
includes taxes & fees
Sep 7 - Sep 8
Cozy, dog-friendly, downtown

15. 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 $393
CA $707 total
includes taxes & fees
Sep 7 - Sep 8
Exclusive Wooded Chalet w Magnificent River Views

16. Towpath Loft -Bike Storage, Downtown Brunswick, MD

Towpath Loft -Bike Storage, Downtown Brunswick, MD
Brunswick
The price is CA $104
CA $277 total
includes taxes & fees
Sep 7 - Sep 8
Towpath Loft -Bike Storage, Downtown Brunswick, MD

17. Patty's Place - Private and Convenient Apartment near Downtown

Patty's Place - Private and Convenient Apartment near Downtown
Frederick
10.0 out of 10, Exceptional, (17 reviews)
"Place was perfect and tbe location great. East in and out town..or to get to down town"
United States
Andrew
The price is CA $91
CA $293 total
includes taxes & fees
Sep 7 - Sep 8
Patty's Place - Private and Convenient Apartment near Downtown

18. Camp Patowmack - Riverfront, Hot Tub, and Sauna!

Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Harpers Ferry
9.4 out of 10, Exceptional, (10 reviews)
"Great house with a beautiful view. "
United States
Sandra A.
The price is CA $180
CA $846 total
includes taxes & fees
Sep 9 - Sep 10
Camp Patowmack - Riverfront, Hot Tub, and Sauna!

19. Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
9.8 out of 10, Exceptional, (11 reviews)
"We had a great time. It was a great location to be close to the aid station for the C&O ultra. Great coffee shop nearby. It was comfortable and nice. Owners were very communicative."
United States
Angele C.
The price is CA $182
CA $346 total
includes taxes & fees
Sep 10 - Sep 11
Historic Getaway near C&O Canal, hiking and biking
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?

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath: This vacation home rental near Boonsboro is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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, Washington Monument State Park and South Mountain 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.