A waterfall cascading over rocks surrounded by lush greenery.

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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
9.8 out of 10, Exceptional, (10 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 AED 407
AED 781 total
includes taxes & fees
9 Nov - 10 Nov
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

2. 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.
The price is AED 550
AED 1,114 total
includes taxes & fees
8 Nov - 9 Nov
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

3. 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 AED 4,086
AED 8,682 total
includes taxes & fees
8 Nov - 9 Nov
Beautiful Mansion in the Country & Wedding Venue

4. 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.
The price is AED 349
AED 946 total
includes taxes & fees
8 Nov - 9 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown

5. 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 AED 514
AED 963 total
includes taxes & fees
8 Dec - 9 Dec
Rancher in Mont Alto

6. 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"
United States
Mary F.
The price is AED 444
AED 1,538 total
includes taxes & fees
13 Nov - 14 Nov
Rural & Historic Detour Escape w/ Horses On-Site!

7. 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"
United States
Dave T.
The price is AED 367
AED 927 total
includes taxes & fees
12 Nov - 13 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

8. 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. "
United States
Brandon K.
The price is AED 309
AED 1,328 total
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!

9. 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.
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

10. 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, (120 reviews)
"Beautiful, quiet property, and the hosts were great to work with!"
United States
Matthew L.
The price is AED 410
AED 502 total
includes taxes & fees
9 Nov - 10 Nov
Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!

11. 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, (75 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is AED 349
AED 923 total
includes taxes & fees
8 Nov - 9 Nov
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

12. 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
Cozy Downtown Cabin - Family Friendly

13. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (12 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. "
United States
Tereasa G.
The price is AED 625
AED 1,453 total
includes taxes & fees
9 Nov - 10 Nov
New townhouse

14. 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 Gettysburg
Fairfield
9.8 out of 10, Exceptional, (52 reviews)
"Awesome place."
United States
Holly J.
The price is AED 1,469
AED 2,198 total
includes taxes & fees
8 Nov - 9 Nov
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

15. 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 Hill
Gettysburg Historic District
10.0 out of 10, Exceptional, (79 reviews)
"Tidy, comfortable and historical rental property with easy walking distance to shops and restaurants."
United States
Ken L.
The price is AED 410
AED 1,485 total
includes taxes & fees
9 Nov - 10 Nov
Spacious 1 BR Stratton House: A Cozy Downtown Stay Backing to Culp's Hill

16. Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6

Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6
Orrtanna
9.8 out of 10, Exceptional, (18 reviews)
"Just perfect, love this place definitely coming back when I stay in Pennsylvania"
United States
William G.
The price is AED 563
AED 1,088 total
includes taxes & fees
8 Nov - 9 Nov
Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6

17. Dog-Friendly | Hiking| Tubing near Harpers Ferry

Dog-Friendly | Hiking| Tubing near Harpers Ferry
Brunswick
2.0 out of 10, (1 review)
"No ac just window units it was soooooo hot"
United States
Anonymous traveler
The price is AED 461
AED 817 total
includes taxes & fees
17 Nov - 18 Nov
Dog-Friendly | Hiking| Tubing near Harpers Ferry

18. 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 Inn
Orrtanna
9.8 out of 10, Exceptional, (61 reviews)
"Spacious and pool table was nice addition Host was very accessible and accommodating"
United States
Christopher C.
The price is AED 628
AED 1,240 total
includes taxes & fees
16 Nov - 17 Nov
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn

19. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown 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."
United States
Jessica
The price is AED 569
AED 1,198 total
includes taxes & fees
1 Dec - 2 Dec
Luxury Condo In Downtown Frederick

20. Inns of Whitetail #108

Inns of Whitetail #108
Mercersburg
6.0 out of 10, (2 reviews)
"Absolutely amazing ! Very clean and Check in was super easy . "
United States
Tiffany B.
The price is AED 573
AED 1,026 total
includes taxes & fees
8 Nov - 9 Nov
Inns of Whitetail #108
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