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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, (4 reviews)
"The house was adorable, the personalized touches, snack basket and welcome note were awesome and made our day. The host was very nice and welcoming. We had a wonderful time."
United States
Bill C.
The price is AED 430
AED 857 total
includes taxes & fees
2 Sep - 3 Sep
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (154 reviews)
"Great place to stay. Very clean and beautiful. The Host was very nice too and kept us informed. We will definetly stay there again!"
United States
Adair M.
The price is AED 312
AED 892 total
includes taxes & fees
2 Sep - 3 Sep
Charming "Cream of the Crop" Cape ~❤️of Middletown

3. Rancher in Mont Alto

Rancher in Mont Alto
Mont Alto
10.0 out of 10, Exceptional, (12 reviews)
"Absolutely wonderful place. Very clean and comfortable. Wonderful neighborhood with beautiful scenery."
United States
Brandon P.
Rancher in Mont Alto

4. Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.6 out of 10, Exceptional, (210 reviews)
"Great place, pet friendly. "
United States
Doug P.
The price is AED 533
AED 646 total
includes taxes & fees
7 Sep - 8 Sep
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

5. 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, (109 reviews)
"Beautiful, quiet property, and the hosts were great to work with!"
United States
Matthew L.
The price is AED 426
AED 551 total
includes taxes & fees
2 Sep - 3 Sep
Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!

6. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (97 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is AED 579
AED 1,279 total
includes taxes & fees
2 Sep - 3 Sep
Luxury Condo In Downtown Frederick

7. Rural & Historic Detour Escape w/ Horses On-Site!

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.0 out of 10, Wonderful, (6 reviews)
"We had a great time. It is an older house but wonderful. It is in the country with lots of green fields surrounding it. The porch with the rockers was my favorite place to be when we weren’t site seeing, It was so peaceful. I would definitely stay here again."
United States
Charla H.
The price is AED 444
AED 1,624 total
includes taxes & fees
9 Sep - 10 Sep
Rural & Historic Detour Escape w/ Horses On-Site!

8. 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, (72 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is AED 312
AED 888 total
includes taxes & fees
3 Sep - 4 Sep
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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
9.4 out of 10, Exceptional, (136 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is AED 448
AED 1,078 total
includes taxes & fees
2 Sep - 3 Sep
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

10. 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 4,132
AED 8,793 total
includes taxes & fees
2 Sep - 3 Sep
Beautiful Mansion in the Country & Wedding Venue

11. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
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)
"Everything was great!"
United States
Corey G.
The price is AED 1,469
AED 2,307 total
includes taxes & fees
2 Sep - 3 Sep
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

13. 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)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
The price is AED 694
AED 1,620 total
includes taxes & fees
2 Sep - 3 Sep
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

14. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (20 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 1,838 total
includes taxes & fees
2 Sep - 3 Sep
Newly constructed 6 bedroom home

15. Beautiful rustic/newly renovated Home near Gettysburg, PA

Beautiful rustic/newly renovated Home near Gettysburg, PA
Orrtanna
10.0 out of 10, Exceptional, (49 reviews)
"We loved our stay. Perfect location near Gettysburg.kids loved this place."
United States
Jason B.
The price is AED 856
AED 1,521 total
includes taxes & fees
7 Sep - 8 Sep
Beautiful rustic/newly renovated Home near Gettysburg, PA

16. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (11 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.
New townhouse

17. 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, (16 reviews)
"Great location for the Spring Festival. The beds were very comfortable. Kitchen was well equipped ."
United States
Renee W.
The price is AED 1,010
AED 1,670 total
includes taxes & fees
7 Sep - 8 Sep
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

18. Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (20 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
The price is AED 1,043
AED 1,803 total
includes taxes & fees
7 Sep - 8 Sep
Exclusive Wooded Chalet w Magnificent River Views

19. 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, (60 reviews)
"Very nice stay. Close to everything and great amenities. Will definitely stay again if we are back in the area"
United States
Cammeron F.
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn

20. 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 672
AED 1,313 total
includes taxes & fees
13 Sep - 14 Sep
Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6
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