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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...
United States
Julianne L.
The price is AED 400
AED 880 total
includes taxes & fees
10 Nov - 11 Nov
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

2. 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
10 Nov - 11 Nov
Beautiful Mansion in the Country & Wedding Venue

3. 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 1,160 total
includes taxes & fees
9 Dec - 10 Dec
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (162 reviews)
"Great little spot!"
United States
Shelby W.
The price is AED 459
AED 1,075 total
includes taxes & fees
15 Nov - 16 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 463
AED 902 total
includes taxes & fees
10 Nov - 11 Nov
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. 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 441
AED 1,523 total
includes taxes & fees
29 Nov - 30 Nov
Spacious 1 BR Stratton House: A Cozy Downtown Stay Backing to Culp's Hill

8. 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
16 Nov - 17 Nov
Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!

9. 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.

10. 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 312
AED 884 total
includes taxes & fees
11 Nov - 12 Nov
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

11. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is AED 698
AED 802 total
includes taxes & fees
25 Nov - 26 Nov
Cozy Downtown Cabin - Family Friendly

12. 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
10 Nov - 11 Nov
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

13. New townhouse

New townhouse
Frederick
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. "
United States
Tereasa G.
The price is AED 760
AED 1,604 total
includes taxes & fees
10 Dec - 11 Dec
New townhouse

14. 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 565
AED 1,144 total
includes taxes & fees
1 Dec - 2 Dec
Luxury Condo In Downtown Frederick

15. 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 1,119 total
includes taxes & fees
15 Nov - 16 Nov
Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6

16. Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Sharpsburg
8.2 out of 10, Very good, (66 reviews)
"I was surprised to see how dilapidated the decking around the house was. I was concerned we might trip or fall through. The location was ideal for bicycling and fishing . The backyard was beautiful with the most prettiest flowers and trees."
United States
Susie R.
The price is AED 704
AED 1,544 total
includes taxes & fees
30 Nov - 1 Dec
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

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 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
7 Dec - 8 Dec
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn

18. 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

19. Relax near Gettysburg ski/wineries/fire pit!

Relax near Gettysburg ski/wineries/fire pit!
Orrtanna
10.0 out of 10, Exceptional, (54 reviews)
"Wonderful property, very cozy!"
United States
Lisa G.
The price is AED 1,045
AED 1,754 total
includes taxes & fees
10 Dec - 11 Dec
Relax near Gettysburg ski/wineries/fire pit!

20. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
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!"
United States
Janice M.
The price is AED 782
AED 1,740 total
includes taxes & fees
10 Nov - 11 Nov
Newly constructed 6 bedroom home
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