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Compare 170 Vacation Homes in Smithsburg with updated reviews, rates, and availability.

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.6 out of 10, Exceptional, (89)
"Great year round location. Owners are nearby if issues occur. HIGHLY RECOMMENDED. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

1852 Historic Stone home

10.0 out of 10, Exceptional, (106)
"Convenient location and within walking districts restaurants and bars"
The price is AED 1,084
AED 2,015 total
includes taxes & fees
6 Jan - 7 Jan
1852 Historic Stone home

The Peaceful Nest

The price is AED 661
AED 1,184 total
includes taxes & fees
3 Feb - 4 Feb
The Peaceful Nest

Gettysburg Family Retreat - 4 BR Pet Friendly!

9.2 out of 10, Wonderful, (16)
"Very clean home located in beautiful Adams County countryside. Perfect for three couples coming for Friendsgiving and Gettysburg events. A little trouble with the heat furnace but we figured it out. The property manager was responsive to our outreach. We would recommend the property and stay again. Thank you Tom and Kevin. "
Gettysburg Family Retreat - 4 BR Pet Friendly!

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

10.0 out of 10, Exceptional, (117)
"We were looking for a quiet getaway location from the Black Friday and Small Business Saturday crowds, but also a location that was close to several small towns near the area...and this property checked all boxes! Everywhere you go within 20-30 minutes is a delight for the history, art, music collector, foodie, entertainment, wine, distillery, brewery, or shopping fanatic...a delightful home and one we hope to visit again!"
The price is AED 349
AED 907 total
includes taxes & fees
5 Jan - 6 Jan
Charming "Cream of the Crop" Cape ~❤️of Middletown

Gettysburg Getaway! Battlefields/Wineries/Ski!

9.8 out of 10, Exceptional, (29)
"This area is quiet and close to Gettysburg. The house is very nice and roomy. I would recommend staying at this property."
Gettysburg Getaway! Battlefields/Wineries/Ski!

Homey 'Ridgetop Retreat' - Walk to Hiking & Biking

10.0 out of 10, Exceptional, (12)
"10/10 would recommend very kid friendly. "
Homey 'Ridgetop Retreat' - Walk to Hiking & Biking

Historic civil war home and estate in Gettysburg you can rent privately.

9.2 out of 10, Wonderful, (26)
"We had such a fun trip! Historic Rainworth Lodge was a cozy and convenient spot to rest after exploring the town and battlefields. Daniel was so accommodating and responded immediately to any questions we had. We enjoyed our time in the house and felt very comfortable. It was interesting to learn about the history of the place as well! "
The price is AED 1,286
AED 1,610 total
includes taxes & fees
4 Jan - 5 Jan
Historic civil war home and estate in Gettysburg you can rent privately.

Cozy Cow | 4 Bed, 2 Bath

10.0 out of 10, Exceptional, (44)
"The house and surrounding farm are absolutely stunning! The house is cozy, comfortable and offers everything you could possibly hope for in a vacation property. The perfect getaway to enjoy family and friends. My wife and I hated to leave!"
Cozy Cow | 4 Bed, 2 Bath

The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing, & Hiking

9.8 out of 10, Exceptional, (47)
"This was just as described! The location was perfect for Gettysburg and Maryland. We were able to go exploring and make a short trip back to relax."
The price is AED 569
AED 1,221 total
includes taxes & fees
5 Jan - 6 Jan
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing, & Hiking

Historic Civil War house, great for family getaways.

9.8 out of 10, Exceptional, (141)
"this property is everything and MORE. absolutely stunning property. the location couldn’t be any better for all things Gettysburg. The only issue we had was the front door is exceptionally old and difficult to lock. we are planning on coming back and staying again in Spring. love love love would not recommend for small kids as some of the furniture is antique."
Historic Civil War house, great for family getaways.

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

9.6 out of 10, Exceptional, (174)
"I had a great time at this beautiful historic house. The hosts are so great and helpful! This house is a historic home with so much interesting architecture. The home is in a beautiful location as well! Loved it!"
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry

9.6 out of 10, Exceptional, (15)
"Very accommodating property close to Harper's Ferry with an abundance of beautiful scenery and close to many historical sites."
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (123)
"I come to Frederick a lot and so have stayed at many of the VRBO properties. This property is the best property I have seen in Frederick in terms of comfort and aesthetic appeal. Everything was super nice and classy from the linens to the dishware. It is in an excellent location within a short walk to Market street and the canal. The host is really nice and very accommodating. I strongly recommend it especially if you want to be downtown."
Gorgeous 1840 Log Cabin- Downtown

Ideal for groups and families! Gathering spaces on all 3 levels! ADA accessible!

10.0 out of 10, Exceptional, (49)
"Our family of 6 adults and a one year old thoroughly enjoyed the house and the great location. The home is furnished in a lovely, comfortable style with some glamorous touches. The easy walk around town to shops and restaurants was most enjoyable. The hosts couldn't be nicer and made us feel so welcome with special treats."
Ideal for groups and families! Gathering spaces on all 3 levels! ADA accessible!

Culp House: Ideal Location, Historic Gettysburg! Can Rent with the Cricket House

10.0 out of 10, Exceptional, (153)
"The Culp House did not disappoint. We all felt very much at home and cozy. Clean, spacious and comfortable. We stayed off season so it was too cold to sit outside, but great outdoor space for warmer months. Five minute walk to town square with restaurants and shops. If you plan to cook be prepared to bring some basics like spices, plastic wrap, etc. We highly recommend staying here. "
Culp House: Ideal Location, Historic Gettysburg! Can Rent with the Cricket House

Historic Chambersburg Home w/ Pool + Game Rooms!

10.0 out of 10, Exceptional, (5)
"We stayed here while in town for a wedding. We had 13 adults and one child. This is such a neat old house with so many cool features. We had a fun time exploring the house and admiring the unique features like the Jefferson doors to the porches, the old coal dump, and all the super cool antiques in the home. All of the bedrooms have a sink in them which was really awesome and helpful for when we were all getting ready at the same time. Our only feedback is that the pillows were a little hard and...
Historic Chambersburg Home w/ Pool + Game Rooms!

Visit our charming cottage this Spring. Enjoy the blooming flowers and scenery.

9.8 out of 10, Exceptional, (37)
"Felt right at home staying here. A short drive to Gettysburg. Would definitely stay here and and will be recommending it to friends. "
Visit our charming cottage this Spring. Enjoy the blooming flowers and scenery.

Peaceful Home w/ Patio < 2 Mi to Nat'l Park!

10.0 out of 10, Exceptional, (17)
"Everything was perfect, and comfortable. Owners really care about their visitors. Home was walk in perfect for a family long weekend. Happened to be Thurmont's annual colorfest festival, and home pefectly located, nestled away yet close enough for easy walking. Highly recommend. "
Peaceful Home w/ Patio < 2 Mi to Nat'l Park!

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

9.8 out of 10, Exceptional, (44)
"Stunning property and well-maintained. I only wish we had more time here! Eileen was incredibly accommodating and flexible with our check-in. "
The price is AED 1,469
AED 2,307 total
includes taxes & fees
5 Jan - 6 Jan
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
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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Other property types in Smithsburg

Secluded Farm Getaway In Smithsburg

9.4 out of 10, Exceptional, (53)
"The house had everything we needed for a pleasant stay. Nice and secluded for a quiet stay. Some lights didn't work, including the lights in the basement near the washer and dryer."
Secluded Farm Getaway In Smithsburg

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (49)
"Excellent little cabin right on the river and close to DT Sheperdstown which is a great town."
The price is AED 162
AED 403 total
includes taxes & fees
14 Jan - 15 Jan
❤️ Secluded 1940s Romantic Tiny House on the River

Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

9.4 out of 10, Exceptional, (206)
"Enjoyed this stay right next to a beautiful trout stream with and Woods . We had everything we needed along with YouTube tv available to sign into. (Glad we started YouTube tv so it made it easy to have all our saved programs for this trip. Had a great time in Gettysburg ."
Cozy streamside cabin, convenient to Ski Liberty and Gettysburg
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.