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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Boonsboro vacation rentals

A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

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.
$323 nightly
The price is $334
Oct 18 - Oct 19
Total with taxes and fees
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
Private kitchen

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

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
$295 nightly
The price is $313
Oct 20 - Oct 21
Total with taxes and fees
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
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, (100 reviews)
"We had a lovely get-away! Really enjoyed ourselves."
United States
Erinn
$313 nightly
The price is $332
Oct 18 - Oct 19
Total with taxes and fees
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, (76 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
$350 nightly
The price is $390
Nov 3 - Nov 4
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

5. 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.
$244 nightly
The price is $259
Oct 26 - Oct 27
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (159 reviews)
"Perfect little house in a great historic location."
United States
Donald K.
$237 nightly
The price is $251
Oct 18 - Oct 19
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

7. 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, (19 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
$426 nightly
The price is $452
Oct 29 - Oct 30
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (87 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
$96 nightly
The price is $107
Oct 25 - Oct 26
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
A bedroom with a bed, a dresser, a ceiling fan, and a window with blinds.

9. 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
$217 nightly
The price is $230
Nov 15 - Nov 16
Total with taxes and fees
Cozy Downtown Cabin - Family Friendly
A living room with a dining table, chairs, a sofa, and a television.

10. 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.
$199 nightly
The price is $221
Oct 18 - Oct 19
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

11. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (55 reviews)
"Nice little place. Hosts were very responsive."
United States
Miki M.
$252 nightly
The price is $280
Nov 12 - Nov 13
Total with taxes and fees
Charming Cabin in the Woods with River Access
A rustic, cylindrical structure with a thatched roof, a small seating area, and a view of the surrounding forest.

12. 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.
$209 nightly
The price is $210
Oct 18 - Oct 19
Total with taxes and fees
Bin There Treehouse - A Grain Bin treehouse!
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

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, (70 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
$170 nightly
The price is $180
Oct 19 - Oct 20
Total with taxes and fees
Cozy Getaway near Harper`s Ferry, C&O & Potomac
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
$401 nightly
The price is $449
Oct 20 - Oct 21
Total with taxes and fees
Large Family Home: 5 Mi to Dtwn Hagerstown!
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

15. 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.
$406 nightly
The price is $452
Oct 20 - Oct 21
Total with taxes and fees
Large Family Home: 5 Mi to Dtwn Hagerstown!
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

16. 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.
$237 nightly
The price is $251
Oct 18 - Oct 19
Total with taxes and fees
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A covered outdoor seating area with wicker furniture and a table, overlooking a parking lot and a building with a sign reading "1799 INN".

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

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (60 reviews)
"Location is unbeatable- but bring ear plugs for the train whistling through the night."
United States
Karla
$206 nightly
The price is $229
Nov 1 - Nov 2
Total with taxes and fees
Best location! The Pullman Apt @ historic 1799 Inn
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

18. 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.
$189 nightly
The price is $200
Oct 19 - Oct 20
Total with taxes and fees
Beautiful, Historic, Hiking, Biking and C&O Canal
A deck with green chairs and a fire pit, surrounded by a house and trees.

19. 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.
$472 nightly
The price is $500
Oct 19 - Oct 20
Total with taxes and fees
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A two-story house with a porch decorated with string lights and garlands.

20. 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, (13 reviews)
"Very friendly host who made communications easy. We left our iPad behind and they called us right away. The apartment was large, beds were comfortable, and the bathroom renovation was beautiful with a great shower. It is about a block from the C&O trail plus free parking on the property."
United States
Kelly
$236 nightly
The price is $250
Oct 18 - Oct 19
Total with taxes and fees
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

Days Inn by Wyndham Frederick

Days Inn by Wyndham Frederick

8/10 Good
"Due to old age and limited mobility, I need to choose hotels where I can park right at the door to the room, like this Days Inn. The room was clean, the bed was comfortable, and the surroundings were very quiet. It is a budget property, so don't check in expecting luxury."
robert 1-night trip
Posted 18 hours ago
Days Inn by Wyndham Frederick

Find out more about Boonsboro

Everything you need to know about Boonsboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Boonsboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Boonsboro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Boonsboro vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Boonsboro. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Boonsboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $248 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Boonsboro rentals

At Expedia, we put the best Boonsboro vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Boonsboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Boonsboro vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Boonsboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.