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Smithsburg Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Smithsburg vacation rentals

A rustic, cylindrical structure with a thatched roof, a small seating area, and a view of the surrounding forest.

1. 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.
The price is AEDĀ 532
AEDĀ 738 total
includes taxes & fees
12 Nov - 13 Nov
Bin There Treehouse - A Grain Bin treehouse!
A lakeside setting with wooden chairs and a picnic table, surrounded by lush greenery and trees.

2. Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Waynesboro
9.8 out of 10, Exceptional, (110 reviews)
"This was our 4th stay and enjoyed every one!"
United States
Anonymous traveler
The price is AEDĀ 294
AEDĀ 788 total
includes taxes & fees
12 Nov - 13 Nov
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
A bathroom with a towel rack, a mirror, a sink, and a potted plant.

3. Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Highfield-Cascade
10.0 out of 10, Exceptional, (11 reviews)
"I cannot say enough about the wonderful time we had staying at Denise & Mike's lovely cottage. They went above and beyond to make sure our family gathering was perfect...and it truly was. Sitting on the front porch sharing coffee in the a.m. and wine in the evening. Board games, chats and laughter until our bellies ached. Our family spent our much needed reunion sharing long overdue times making more wonderful memories. Upon arrival we found the property even more special than we imagined from...
United States
Julianne L.
The price is AEDĀ 426
AEDĀ 911 total
includes taxes & fees
22 Nov - 23 Nov
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
A house with a covered porch, two wicker chairs, a welcome sign, and a hanging flower basket.

4. 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, (21 reviews)
"Great spot close to the wedding venue!!"
United States
Alfred T.
The price is AEDĀ 225
AEDĀ 622 total
includes taxes & fees
12 Nov - 13 Nov
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

5. Bright 2-Bed ADA Room|Free Parking

Bright 2-Bed ADA Room|Free Parking
Hagerstown
10.0 out of 10, Exceptional, (3 reviews)
"Bed firm yet cozy providing restful support during our stay of one night."
United States
Anonymous traveler
The price is AEDĀ 232
AEDĀ 260 total
includes taxes & fees
10 Dec - 11 Dec
Bright 2-Bed ADA Room|Free Parking
A stone pathway leading to a house with a statue in the foreground.

6. Beautiful Mansion in the Country & Wedding Venue

Beautiful Mansion in the Country & Wedding Venue
Waynesboro
9.8 out of 10, Exceptional, (9 reviews)
"The stay and place was awesome and my family and I will definitely be booking again "
United States
Comedy C.
The price is AEDĀ 4,086
AEDĀ 8,682 total
includes taxes & fees
13 Nov - 14 Nov
Beautiful Mansion in the Country & Wedding Venue
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

7. ā¤ļø Secluded 1940s Romantic Tiny House on the River

ā¤ļø 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.
The price is AEDĀ 169
AEDĀ 380 total
includes taxes & fees
18 Nov - 19 Nov
ā¤ļø Secluded 1940s Romantic Tiny House on the River
A rustic building with a sign reading 'The Robin's Nest' and a front door.

8. 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)
"Cute place with a lot of character. Host was very responsive. We enjoyed our sray."
United States
Dawn V.
The price is AEDĀ 550
AEDĀ 1,160 total
includes taxes & fees
12 Nov - 13 Nov
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

9. Vintage cabin in the ā¤ļø of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ā¤ļø of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (118 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 AEDĀ 312
AEDĀ 779 total
includes taxes & fees
15 Nov - 16 Nov
Vintage cabin in the ā¤ļø of Middletown , MD. Pet friendly and prime location.
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

10. Spacious King Bed | Free Parking

Spacious King Bed | Free Parking
Hagerstown
10.0 out of 10, Exceptional, (3 reviews)
"Checking in took no time, plus blackout curtains provided just the right setting for sleeping soundly at night."
United States
Anonymous traveler
The price is AEDĀ 261
AEDĀ 292 total
includes taxes & fees
6 Dec - 7 Dec
Spacious King Bed | Free Parking
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

11. Cozy 2-bed ADA Room | Free Parking

Cozy 2-bed ADA Room | Free Parking
Hagerstown
10.0 out of 10, Exceptional, (2 reviews)
"Convenient parking spot near entrance added ease to arrivals and departures every day of our trip!"
United States
Anonymous traveler
The price is AEDĀ 232
AEDĀ 260 total
includes taxes & fees
6 Dec - 7 Dec
Cozy 2-bed ADA Room | Free Parking
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

12. Spacious 2-Bed Queen | Free Parking

Spacious 2-Bed Queen | Free Parking
Hagerstown
10.0 out of 10, Exceptional, (2 reviews)
"Quiet place with comfy beds. Not too fancy but better than some cheaper options nearby."
United States
Anonymous traveler
The price is AEDĀ 232
AEDĀ 260 total
includes taxes & fees
6 Dec - 7 Dec
Spacious 2-Bed Queen | Free Parking
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

13. Charming "Cream of the Crop" Cape ~ā¤ļøof Middletown

Charming "Cream of the Crop" Cape ~ā¤ļøof Middletown
Middletown
10.0 out of 10, Exceptional, (162 reviews)
"Great little spot!"
United States
Shelby W.
The price is AEDĀ 367
AEDĀ 966 total
includes taxes & fees
15 Nov - 16 Nov
Charming "Cream of the Crop" Cape ~ā¤ļøof Middletown
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

14. Cozy King Bed | Free Wifi & Parking

Cozy King Bed | Free Wifi & Parking
Hagerstown
10.0 out of 10, Exceptional, (2 reviews)
"Having both a fridge and microwave right in the room turned out very useful!"
United States
Anonymous traveler
The price is AEDĀ 261
AEDĀ 292 total
includes taxes & fees
6 Dec - 7 Dec
Cozy King Bed | Free Wifi & Parking
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

15. Clean 2-bed Queen | Free Parking

Clean 2-bed Queen | Free Parking
Hagerstown
8.8 out of 10, Excellent, (3 reviews)
"We liked how the double bed felt solid but soft enough for a restful night's sleep together after long drives each day"
United States
Anonymous traveler
The price is AEDĀ 232
AEDĀ 260 total
includes taxes & fees
6 Dec - 7 Dec
Clean 2-bed Queen | Free Parking
A cozy room with a grey sofa, a small bedside table with a lamp, and a window with curtains.

16. Rancher in Mont Alto

Rancher in Mont Alto
Mont Alto
9.8 out of 10, Exceptional, (17 reviews)
"Great place to stay"
United States
Austin B.
The price is AEDĀ 463
AEDĀ 902 total
includes taxes & fees
17 Nov - 18 Nov
Rancher in Mont Alto
A living room with a sofa, a TV mounted on the wall, and a large sliding glass door leading to a garden.

17. Galloping Getaway on the rolling hills of GemStone Stable

Galloping Getaway on the rolling hills of GemStone Stable
Hagerstown
10.0 out of 10, Exceptional, (33 reviews)
"We loved staying here. Beautiful views, great communication with Tammie, and very clean. Definitely will stay again!"
United States
Haley H.
The price is AEDĀ 459
AEDĀ 672 total
includes taxes & fees
12 Nov - 13 Nov
Galloping Getaway on the rolling hills of GemStone Stable
A compact kitchen with a coffee machine, microwave, and a small cart with kitchen tools.

18. Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Frederick
10.0 out of 10, Exceptional, (18 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 AEDĀ 258
AEDĀ 760 total
includes taxes & fees
22 Nov - 23 Nov
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
A compact RV interior with a kitchenette, a seating area, and a small dining space.

19. Serenity Airstream at Apple Blossom Farm, Hot Tub is Extra

Serenity Airstream at Apple Blossom Farm, Hot Tub is Extra
Orrtanna
10.0 out of 10, Exceptional, (119 reviews)
"Great stay! Thank you!!!"
United States
JULIE M.
The price is AEDĀ 349
AEDĀ 779 total
includes taxes & fees
12 Nov - 13 Nov
Serenity Airstream at Apple Blossom Farm, Hot Tub is Extra
A spacious living area with a large window, a wooden ceiling, and a dining area with a table and chairs.

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

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (24 reviews)
"Relaxing, close to all."
United States
Valarie
The price is AEDĀ 367
AEDĀ 1,375 total
includes taxes & fees
18 Nov - 19 Nov
Peregrine's Perch - Cabin Overlooking the River!
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 Smithsburg 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

Free breakfast was good. Staff friendly
United States
Christine
Reviewed November 10, 2026
Fairfield Inn & Suites by Marriott Hagerstown

Frequently Asked Questions

Can I find a vacation rental in Smithsburg?

Yes, we offer vacation rentals close to the most popular sights in Smithsburg, or you can select a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals that Smithsburg has to offer?

Unique Gettysburg Barn Loft central to Gettysburg and Ski Liberty!: Visitors like this Smithsburg vacation home rental. It offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Smithsburg?

Choose from 4 Expedia vacation rentals in Smithsburg for a memorable vacation.

What can I see and do in Smithsburg?

Explore the area and family-friendly sights such as Catoctin Wildlife Preserve and Zoo, or get out into nature at a spot like Pen Mar Park. Cunningham Falls State Park and South Mountain State Park are other places to visit while you're in town.

What are vacation rentals like in Smithsburg?

Vacation rentals are private properties you can reserve for a short or long stay in Smithsburg. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family gatherings.