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Our top choices for Smithsburg vacation homes
1. 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...
Julianne L.
The price is CA $165
CA $352 total
includes taxes & fees
Nov 22 - Nov 23
2. Beautiful Mansion in the Country & Wedding Venue
Beautiful Mansion in the Country & Wedding VenueWaynesboro
9.8 out of 10, Exceptional, (9 reviews)
"The stay and place was awesome and my family and I will definitely be booking again "
Comedy C.
The price is CA $1,578
CA $3,388 total
includes taxes & fees
Nov 13 - Nov 14
3. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
Historic Cottage Retreat-IG Hot Tub-Brick Fire PitBoonsboro
9.8 out of 10, Exceptional, (19 reviews)
"Cute place with a lot of character. Host was very responsive. We enjoyed our sray."
Dawn V.
The price is CA $212
CA $453 total
includes taxes & fees
Nov 12 - Nov 13
4. Charming "Cream of the Crop" Cape ~❤️of Middletown
Charming "Cream of the Crop" Cape ~❤️of MiddletownMiddletown
10.0 out of 10, Exceptional, (162 reviews)
"Great little spot!"
Shelby W.
The price is CA $142
CA $376 total
includes taxes & fees
Nov 15 - Nov 16
5. Rancher in Mont Alto
Rancher in Mont AltoMont Alto
9.8 out of 10, Exceptional, (17 reviews)
"Great place to stay"
Austin B.
The price is CA $179
CA $351 total
includes taxes & fees
Nov 17 - Nov 18
6. 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, MDJefferson
10.0 out of 10, Exceptional, (75 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
Tory D.
The price is CA $121
CA $343 total
includes taxes & fees
Nov 12 - Nov 13
7. Spacious 1 BR Stratton House: A Cozy Downtown Stay Backing to Culp's Hill
Spacious 1 BR Stratton House: A Cozy Downtown Stay Backing to Culp's HillGettysburg Historic District
10.0 out of 10, Exceptional, (79 reviews)
"Tidy, comfortable and historical rental property with easy walking distance to shops and restaurants."
Ken L.
The price is CA $170
CA $588 total
includes taxes & fees
Nov 29 - Nov 30
8. RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.Downtown Frederick
9.2 out of 10, Wonderful, (148 reviews)
"Great location. Amenities were perfect for a little bit of an extended stay. Definitely will come back in the future"
Dave T.
The price is CA $142
CA $359 total
includes taxes & fees
Nov 12 - Nov 13
9. Rural & Historic Detour Escape w/ Horses On-Site!
Rural & Historic Detour Escape w/ Horses On-Site!Detour
9.0 out of 10, Wonderful, (8 reviews)
"Lovely! Our host was gracious and helpful. Property was ideal for our family getaway. i’m"
Mary F.
The price is CA $172
CA $597 total
includes taxes & fees
Nov 13 - Nov 14
10. Cozy Downtown Cabin - Family Friendly
Cozy Downtown Cabin - Family FriendlyMiddletown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property. I will definitely stay there again."
Roger
The price is CA $270
CA $311 total
includes taxes & fees
Nov 25 - Nov 26
11. Walk to Stores: Home in Historic Shepherdstown!
Walk to Stores: Home in Historic Shepherdstown!Shepherdstown
9.4 out of 10, Exceptional, (6 reviews)
"Very nice place, the lay out is perfect for multiple adults, we stayed for 10 night for work and it was perfect, we will be back for another long stay soon. "
Brandon K.
The price is CA $119
CA $517 total
includes taxes & fees
Nov 19 - Nov 20
12. Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!
Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!Orrtanna
10.0 out of 10, Exceptional, (121 reviews)
"Beautiful, quiet property, and the hosts were great to work with!"
Matthew L.
The price is CA $158
CA $194 total
includes taxes & fees
Nov 16 - Nov 17
13. Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from GettysburgFairfield
9.8 out of 10, Exceptional, (52 reviews)
"Awesome place."
Holly J.
The price is CA $567
CA $849 total
includes taxes & fees
Nov 12 - Nov 13
14. Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6
Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6Orrtanna
9.8 out of 10, Exceptional, (18 reviews)
"Just perfect, love this place definitely coming back when I stay in Pennsylvania"
William G.
The price is CA $218
CA $432 total
includes taxes & fees
Nov 15 - Nov 16
15. New townhouse
New townhouseFrederick
9.6 out of 10, Exceptional, (13 reviews)
"We had a great time. It was perfect for us. I would highly recommend it to others and would not hesitate to return there when back in the area. "
Tereasa G.
The price is CA $241
CA $564 total
includes taxes & fees
Nov 16 - Nov 17
16. Luxury Condo In Downtown Frederick
Luxury Condo In Downtown FrederickDowntown Frederick
9.2 out of 10, Wonderful, (102 reviews)
"Very convenient location with parking. Prompt communication with owner.
However it needs a good deep clean. My towels were used and muddy like the workmen fixing the deck had just showered there. But I would stay there again if necessary."
Jessica
The price is CA $222
CA $469 total
includes taxes & fees
Dec 2 - Dec 3
17. The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown InnOrrtanna
9.8 out of 10, Exceptional, (61 reviews)
"Our host was prompt on questions and the house was clean and cute. Our family was able to relax and enjoy the property while on vacation"
Ash Lee S.
The price is CA $242
CA $476 total
includes taxes & fees
Nov 26 - Nov 27
18. Dog-Friendly | Hiking| Tubing near Harpers Ferry
Dog-Friendly | Hiking| Tubing near Harpers FerryBrunswick
2.0 out of 10, (1 review)
"No ac just window units it was soooooo hot"
Anonymous traveller
The price is CA $178
CA $318 total
includes taxes & fees
Nov 17 - Nov 18
19. Relax near Gettysburg ski/wineries/fire pit!
Relax near Gettysburg ski/wineries/fire pit!Orrtanna
10.0 out of 10, Exceptional, (55 reviews)
"Wonderful property, very cozy!"
Lisa G.
The price is CA $353
CA $655 total
includes taxes & fees
Nov 30 - Dec 1
20. Newly constructed 6 bedroom home
Newly constructed 6 bedroom homeFrederick
10.0 out of 10, Exceptional, (22 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
Janice M.
The price is CA $302
CA $675 total
includes taxes & fees
Nov 12 - Nov 13
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.
Learn more about Smithsburg
Venture to sights like Cunningham Falls State Park and Pen Mar Park as you discover Smithsburg.
Photo by Willow Rock
Open Photo by Willow Rock
Top reviews in Smithsburg
Hampton Inn Hagerstown
Hampton Inn HagerstownHagerstown
10/10 Excellent
Staff was very friendly. Room was very clean. Overall a good stay at Hampton Inn again.
Susan
