Boonsboro Vacation Rentals

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Check prices for these dates

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

Our top choices for Boonsboro vacation rentals

A wooden cabin with a patio area, outdoor seating, and a fire pit.

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, (19 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
$294 nightly
The price is $303
Nov 8 - Nov 9
Total with taxes and fees
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A room with large windows, wooden floors, and a ceiling fan.

2. 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
$311 nightly
The price is $330
Nov 8 - Nov 9
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.

3. 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
$418 nightly
The price is $467
Nov 19 - Nov 20
Total with taxes and fees
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.

4. 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.
$355 nightly
The price is $396
Nov 18 - Nov 19
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

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, (22 reviews)
"Our stay was so enjoyable!"
United States
Kimberly C.
$407 nightly
The price is $431
Nov 16 - Nov 17
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A wooden deck with a grill, outdoor seating, and a bottle of wine.

6. 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, (55 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.
$291 nightly
The price is $325
Nov 9 - Nov 10
Total with taxes and fees
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.

7. 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
$237 nightly
The price is $251
Nov 9 - Nov 10
Total with taxes and fees
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.

8. 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.
$194 nightly
The price is $206
Nov 8 - Nov 9
Total with taxes and fees
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.

9. ❤️ 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.
$88 nightly
The price is $98
Nov 15 - Nov 16
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

10. 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.
$243 nightly
The price is $258
Nov 8 - Nov 9
Total with taxes and fees
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.

11. 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.
$242 nightly
The price is $269
Nov 12 - Nov 13
Total with taxes and fees
Charming Cabin in the Woods with River Access
A living room with a dining table, chairs, a sofa, and a television.

12. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (27 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
$189 nightly
The price is $211
Nov 8 - Nov 9
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

13. 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.

14. 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.
$217 nightly
The price is $218
Nov 10 - Nov 11
Total with taxes and fees
Bin There Treehouse - A Grain Bin treehouse!
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.
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.

16. 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.
$293 nightly
The price is $327
Nov 12 - Nov 13
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A cozy living room with wooden walls, a flat-screen TV, a fireplace, and comfortable seating.

17. 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
$207 nightly
The price is $231
Nov 8 - Nov 9
Total with taxes and fees
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.

18. 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
$196 nightly
The price is $218
Nov 9 - Nov 10
Total with taxes and fees
Best location! The Pullman Apt @ historic 1799 Inn
A spacious living room with a large window, a wooden coffee table, and a sofa.

19. Schilling House

Schilling House
3.0 star property
Bolivar
$293 nightly
The price is $314
Nov 29 - Nov 30
Total with taxes and fees
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

An outdoor patio with a fire pit, seating, and a covered area.
Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown
Hagerstown

10/10 Excellent

Staff super helpful. Gym was nice. Breakfast goid bed was comfortable
United States
Claire
Reviewed November 4, 2026
Fairfield Inn & Suites by Marriott Hagerstown

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 $98 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.

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.

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