Photo by Willow Rock

Holiday Homes in Smithsburg

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Smithsburg

Retreat to the Stratton House-Unique Historic District Home-Backs to Culp's Hill

9.8 out of 10, Exceptional, (52)
"Close walking distance to Gettysburg restaurants and short drive to Gettysburg visitor center. "
Retreat to the Stratton House-Unique Historic District Home-Backs to Culp's Hill

Beautiful rustic/newly renovated Home near Gettysburg, PA

10.0 out of 10, Exceptional, (21)
"Great place for a group of friends to stay. Plenty to do locally and at the property. "
The price is NZ$625
includes taxes & fees
17 Aug - 18 Aug
Beautiful rustic/newly renovated Home near Gettysburg, PA

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

10.0 out of 10, Exceptional, (2)
"Beautiful setting with wonderful indoor and outdoor spaces. The house is charming, renovated, updated, clean, and comfortable. Great location for a family gathering to bike, visit the battlefield or visit Shepherdstown. Hosts went above and beyond to be sure we had all we needed. Would definitely stay again if in the area. "
The price is NZ$731
includes taxes & fees
27 Aug - 28 Aug
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (142)
"Charming, nicely restored log home in a great location for downtown. We would definitely stay here again! "
Gorgeous 1840 Log Cabin- Downtown

1852 Historic Stone home

10.0 out of 10, Exceptional, (132)
"Great location! Clean and easy check in and out. Thank you!"
The price is NZ$982
includes taxes & fees
1 Sept - 2 Sept
1852 Historic Stone home

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (65)
"The home was exactly as expected and made for a wonderful family/friend reunion! Perfect for socializing and so close to local shops and restaurants."
The price is NZ$578
includes taxes & fees
15 Sept - 16 Sept
*Luxury Condo In Downtown Frederick*

Hollow Hideaway is perfect for your holiday stay!

10.0 out of 10, Exceptional, (47)
"Very clean, well appointed home, was a great place to stay for a few days while we explored the area. Nice outdoor space to relax and the board games and arcade game were fun for the kids. "
Hollow Hideaway is perfect for your holiday stay!

“The Train Depot” 2nd oldest in the US

10.0 out of 10, Exceptional, (83)
"Great location in downtown Frederick. Cozy and comfortable accommodation with great historic vibes and modern amenities. We would definitely stay here again. "
“The Train Depot” 2nd oldest in the US

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

10.0 out of 10, Exceptional, (52)
"What a charming place to stay in Jefferson. The Rust Rose had everything we needed in a nice location. We would definitely stay here again."
The price is NZ$419
includes taxes & fees
18 Aug - 19 Aug
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Beautiful private property in rural environment overlooking Ski Liberty.

9.6 out of 10, Exceptional, (54)
"Beautiful location. "
Beautiful private property in rural environment overlooking Ski Liberty.

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

9.8 out of 10, Exceptional, (183)
"Wonderful location near Antietam NP, Shepardstown, and Hagerstown. Small home but plenty of room. My family enjoyed their stay"
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sunlight 2BR townhouse w/ private parking in Downtown Frederick

9.2 out of 10, Wonderful, (20)
"The location was perfect for walking just about anywhere we needed to go! Two bedrooms were a plus for me, my husband, and his sister. The half bath downstairs was also appreciated!"
Sunlight 2BR townhouse w/ private parking in Downtown Frederick

Belle on Buford<br>Apt 1-1st Floor

10.0 out of 10, Exceptional, (108)
"From the moment I booked I knew I made the right choice. Kim answered promptly with any questions I had. We enjoyed our weekend at the Belle on Buford. It was perfect for our weekend celebrating my nephews wedding. Close to the venue. We enjoyed our stay. "
Belle on Buford<br>Apt 1-1st Floor

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

9.8 out of 10, Exceptional, (52)
"Stayed here on a recent visit to Gettysburg, traveling with our 10 year old granddaughter and our dog. There were so many nice touches and amenities, and the beds were very comfortable. Communicating with the owner was easy, and the owner went out of their way to be helpful and accomodating. We were pleasantly surprised at how well-stocked the kitchen was, and impressed with the collection of games and pet items. Great stay!"
The price is NZ$621
includes taxes & fees
24 Aug - 25 Aug
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn

Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch

10.0 out of 10, Exceptional, (9)
"Old time charm on the outside; clean, new and modern on the inside. The rental is small, but nicely done with modern features. The stone fireplace is so pretty with an electric stove inside. The bedroom was lovely with a comfy, king bed. The best part is the screened in porch that runs the whole length of the house. There’s a sectional sofa and coffee table, two rockers, and a table with four chairs on the porch. You can appreciate the old windows with their wooden shutters from back in time. We...
Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch

4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet

10.0 out of 10, Exceptional, (14)
"The property was beyond my expectations, as a Combat veteran with Ptsd/TBI I found true peace and tranquillity here, I love the area, so much Military History! Close by, and definitely recommend this beautiful Home! Host was the best I have experienced,,, Thank you!"
4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet

Historic Civil War house, great for family getaways.

9.8 out of 10, Exceptional, (152)
" Nice home in a great location!"
Historic Civil War house, great for family getaways.

Gettysburg Getaway! Battlefields/Wineries/Ski!

9.8 out of 10, Exceptional, (46)
"We really like the house that we stayed in for our trip. There was 6 of us, almost all of us over 60. The kitchen was very modern, the dining room fit us all, the living room was a little small but we made it work. The bedrooms were all very nice with extremely comfortable beds"
Gettysburg Getaway! Battlefields/Wineries/Ski!

Gettysburg Retreat Best place to stay in Gettysburg! Pre-Civil War Home

10.0 out of 10, Exceptional, (302)
"The house is amazing. Perfectly decorated with an extensive library and dvd collection about Gettysburg and the civil war. The location is great too, easy walking distance to the square. Also, a supermarket right across the street. We thoroughly enjoyed our stay."
Gettysburg Retreat Best place to stay in Gettysburg! Pre-Civil War Home

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

9.4 out of 10, Exceptional, (102)
"Very nice old farm house with modern conveniences.. Comfortable and quiet. The antiques brought back memories of me visiting my grandparents back in the day. "
The price is NZ$475
includes taxes & fees
17 Aug - 18 Aug
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Smithsburg Hotel Reviews