A stone tower with a flagpole and an American flag.

Boonsboro Holiday Rentals

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Our top choices for Boonsboro holiday rentals

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 NZ$578
includes taxes & fees
26 Oct - 27 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

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

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
The price is NZ$550
includes taxes & fees
20 Oct - 21 Oct
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland

3. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (100 reviews)
"We had a lovely get-away! Really enjoyed ourselves."
United States
Erinn
The price is NZ$589
includes taxes & fees
12 Oct - 13 Oct
Antietam Creek - Quiet 2 Bedroom Cabin

4. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (45 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
The price is NZ$643
includes taxes & fees
13 Oct - 14 Oct
Antietam Look Out - Incredible Sunset Views!

5. 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 NZ$808
includes taxes & fees
19 Oct - 20 Oct
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

6. 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, (76 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 NZ$866
includes taxes & fees
20 Oct - 21 Oct
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

7. 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, (116 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 NZ$491
includes taxes & fees
26 Oct - 27 Oct
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

8. 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 NZ$814
includes taxes & fees
18 Oct - 19 Oct
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

9. 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)
"Perfect little house in a great historic location."
United States
Donald K.
The price is NZ$438
includes taxes & fees
12 Oct - 13 Oct
Charming "Cream of the Crop" Cape ~❤️of Middletown

10. 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 NZ$452
includes taxes & fees
13 Oct - 14 Oct
Cozy Downtown Cabin - Family Friendly

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (86 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 NZ$190
includes taxes & fees
25 Oct - 26 Oct
❤️ Secluded 1940s Romantic Tiny House on the River

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 NZ$1,565
includes taxes & fees
20 Oct - 21 Oct
Exclusive Wooded Chalet w Magnificent River Views

13. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
The price is NZ$391
includes taxes & fees
18 Oct - 19 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance

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
The price is NZ$800
includes taxes & fees
20 Oct - 21 Oct
Large Family Home: 5 Mi to Dtwn Hagerstown!

15. 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 NZ$438
includes taxes & fees
12 Oct - 13 Oct
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

16. Bin There Treehouse - A Grain Bin treehouse!

Bin There Treehouse - A Grain Bin treehouse!
Washington County
10.0 out of 10, Exceptional, (5 reviews)
"Such a neat place! Very peaceful setting."
United States
Abby G.
The price is NZ$396
includes taxes & fees
18 Oct - 19 Oct
Bin There Treehouse - A Grain Bin treehouse!

17. Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view
3.5 star property
Mercersburg
10.0 out of 10, Exceptional, (26 reviews)
"Great place to unwind and relax."
United States
Candace
The price is NZ$1,100
includes taxes & fees
4 Nov - 5 Nov
Mirror Villas - Modern Retreat with private hot tubs and mountain view

18. 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, (32 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is NZ$883
includes taxes & fees
19 Oct - 20 Oct
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

19. 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.
The price is NZ$814
includes taxes & fees
20 Oct - 21 Oct
Large Family Home: 5 Mi to Dtwn Hagerstown!

20. Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (29 reviews)
"really nice place"
United States
David R.
The price is NZ$352
includes taxes & fees
12 Oct - 13 Oct
Beautiful, Historic, Hiking, Biking and C&O Canal
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Boonsboro holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Boonsboro. 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 Boonsboro. 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 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 holiday 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 Boonsboro short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Boonsboro?

Yes, there are holiday rentals close to the most popular sights in Boonsboro, or you can select a more secluded 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 are some of the best holiday rentals that Boonsboro has to offer?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This holiday home rental outside of Boonsboro is located in the mountains, and has a patio, a BBQ 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 holiday rentals will I find in Boonsboro?

Expedia has 8 holiday 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 holiday rental in Boonsboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Boonsboro. Holiday rentals offer extras like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family gatherings.