Woodsboro Holiday Rentals

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Holiday Rentals in Woodsboro

Round Top Campground
2.0 star property
9.2 out of 10, Wonderful, (10)
"I traveled and stayed for the weekend with 6 adults. If you have kids, this would be fine as we stayed in a premiere cabin. The bunk bed were tight for us. The sleeper sofa was uncomfortable with the bar in your back and the main bed was ok. The place was clean and the shower had a good amount of hot water. The TV couldn’t get a signal to work. The place overall needs some TLC, but it was overall just ok. "
The price is NZ$307
per night
8 Jul - 9 Jul
Round Top Campground
Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, (65)
"Property was beautifully manicured. Cabin was rustic but comfortable with all the comforts of home. I loved sitting on the huge wrap around porch in the morning listening to the birds and watching the sunrise."
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Thaddeus Stevens' Gettysburg Log Home
9.8 out of 10, Exceptional, (160)
"First impressions count and we all thought the house was charming. It is quirky but that is part of the appeal. It is centrally located and easy to walk to all shops and restaurants. It was also very close to the parade on Memorial Day which was nice. The back garden is large and peaceful if the weather is nice enough to sit outside. Kitchen was well stocked and easy to use. The stairs are quite steep to the first floor so it might be something to consider for those with mobility issues. There...
Thaddeus Stevens' Gettysburg Log Home
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Apple Blossom Cottage! HT Extra Cost
10.0 out of 10, Exceptional, (271)
"Apple Blossom Cottage is made for relaxing and enjoying the serenity of nature. Nestled in the woods with only birds and deer for neighbors, this is a great place for a couple's getaway. Walks down the country lane were highlighted by visits from the horses, donkeys, and beautiful shaggy bull. After a day in close-by Gettysburg, the hot tub was a wonderful end to our days. The cottage has everything provided for a comfortable stay, and our host Elizabeth was quick and thorough with all our...
The price is NZ$352
per night
10 Jul - 11 Jul
Apple Blossom Cottage! HT Extra Cost
Downtown location w/ parking. Transit stop across the street. Unit 4 of 4.
9.8 out of 10, Exceptional, (30)
"Perfect for our visit. Easy walking to food and drink. Close to the battlefield. A great stay!"
Downtown location w/ parking. Transit stop across the street. Unit 4 of 4.
Antietam Toll House~ an historic waterfront cabin
9.8 out of 10, Exceptional, (55)
"This was our second time staying at the cabin. Would definitely return for a third time!"
The price is NZ$496
per night
27 Jun - 28 Jun
Antietam Toll House~ an historic waterfront cabin
Cozy streamside cabin, convenient to Ski Liberty and Gettysburg
9.4 out of 10, Exceptional, (192)
"We traveled to the area to participate in the NADD event at the Historic Round Barn. We needed pet friendly for that reason. The cabin was wonderful but the location was not as pet friendly as I would have liked. The cottage was situated right on the road, no shoulders to walk, no place for the dogs to stretch."
Cozy streamside cabin, convenient to Ski Liberty and Gettysburg
Escape to the mountains! Beat the Summer heat!
10.0 out of 10, Exceptional, (265)
"We loved this property! The house was extremely clean and well stocked. The grounds were beautiful. It was a great landing base for us while we explored gettysburg for a long weekend. Would absolutely recommend again. Thanks!"
Escape to the mountains! Beat the Summer heat!
Scenic Mountaintop Villa with Free WiFi & Pool
10.0 out of 10, Exceptional, (2)
"The property manager was outstanding, she communicated with me in a professional and courteous fashion. The house was perfect for our group size."
Scenic Mountaintop Villa with Free WiFi & Pool
Creekside Cabin at Gettysburg
10.0 out of 10, Exceptional, (124)
"This property was clean, quiet, and conveniently located to everything in Gettysburg. The owners were extremely friendly. Our son had fun fishing in Marsh Creek and we enjoyed the fire pit at night. We wish we would have stayed longer!"
Creekside Cabin at Gettysburg
Gettysburg Retreat Best place to stay in Gettysburg! Pre-Civil War Home
10.0 out of 10, Exceptional, (264)
"House was beautiful. Nice and cozy. Town was very beautiful and had a lot of stuff to do. Sandee was easy to communicate with and even stopped by to say hi and check on us."
Gettysburg Retreat Best place to stay in Gettysburg! Pre-Civil War Home
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
9.6 out of 10, Exceptional, (81)
"My wife LOVED it here. Yes it’s an old cabin But it was furnished wonderfully and very comfortable. We had a great stay and have already recommended this place to a few friends. Over all I give it an A and this one ranks up in the top 5 of our vrbo vacation rentals"
The price is NZ$360
per night
30 Jun - 1 Jul
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (104)
"Cute cottage was clean and comfy. Everything you need to make a nice dinner, relax and enjoy the quiet neighborhood."
The price is NZ$575
per night
7 Jul - 8 Jul
Charming "Cream of the Crop" Cape ~❤️of Middletown
Historic Civil War house, great for family getaways.
9.8 out of 10, Exceptional, (128)
"Enjoyed are time there, We especially liked how close it was to every thing. We were able to walk everywhere. Very beautiful."
Historic Civil War house, great for family getaways.
Airstream in Wine Country Hot Tub Extra Cost
10.0 out of 10, Exceptional, (60)
"The airstream was a perfect place to unwind after a day of exploring Gettysburg! We didn’t use the hot tub but it would be perfect in cooler weather! You have your private oasis both inside and outside. Highly recommend."
The price is NZ$328
per night
25 Jul - 26 Jul
Airstream in Wine Country Hot Tub Extra Cost
' Experience ' The History In Downtown Gettysburg! - 2nd floor
9.8 out of 10, Exceptional, (112)
"The owners were very communicative, the beds were very comfy, we loved the walking distance to restaurants, had a great stay"
' Experience ' The History In Downtown Gettysburg! - 2nd floor
Secluded Farm Getaway In Smithsburg
9.4 out of 10, Exceptional, (51)
"Great area to stay in with friends or go hiking! Large yard perfect for dogs and campfires, and pretty close to hiking trails which is very convenient for group traveling."
Secluded Farm Getaway In Smithsburg
Culp House: Ideal Location, Historic Gettysburg! Can Rent with the Cricket House
10.0 out of 10, Exceptional, (142)
"The Cricket House is a great place to stay in Gettysburg. The facilities are very good, comfortable and close to the battlefield and downtown. The furniture is comfortable and plenty of seating for just spending time when relaxing following your hikes on the battlefield."
Culp House: Ideal Location, Historic Gettysburg! Can Rent with the Cricket House
Cozy Maryland Abode - Gas Grill, Near Devil’s Den!
9.0 out of 10, Wonderful, (2)
"Lovely well kept property. It has everything you need. Comfortable beds and convenient location. The only drawback is the front bedroom has LOTS of street noise. I used a fan for white noise and earplugs. It’s on a busy street. Fire Station is nearby too. Great park for kids across the street. Close to a few great restaurants within walking distance."
Cozy Maryland Abode - Gas Grill, Near Devil’s Den!
Historic Victorian in the heart of Gettysburg!
10.0 out of 10, Exceptional, (22)
"We are a group of high school buddies separated by 46 years or so and distance who recently decided to meet up once a year. Having an interest in history, what better place than Gettysburg for 3 or 4 days. The house has that period feel. It was immaculate with all the modern conveniences. Large spacious rooms, inviting back yard. Our visits to the Gettysburg Museum, Battlefield and Cemetery were made all the more memorable by the accommodations. Its location right in the middle of the town was...
Historic Victorian in the heart of Gettysburg!
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See all available properties in Woodsboro
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.

Other types of properties in Woodsboro you may be interested in

Baymont by Wyndham Gettysburg
2.5 star property
7.0 out of 10, Good, (777)
"Property was near the event I was attending and more affordable than the host hotel."
The price is NZ$129
per night
27 Jun - 28 Jun
Baymont by Wyndham Gettysburg
Country Inn & Suites by Radisson, Frederick, MD
3.0 star property
8.6 out of 10, Excellent, (1003)
"Everything was great."
The price is NZ$142
per night
30 Jun - 1 Jul
Country Inn & Suites by Radisson, Frederick, MD
1863 Inn of Gettysburg
3.0 star property
9.2 out of 10, Wonderful, (1002)
"Second time here. They let us check in one hour early, no questions asked. Nice salt water pool. Close to everything. "
The price is NZ$260
per night
7 Jul - 8 Jul
1863 Inn of 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Woodsboro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Woodsboro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Woodsboro. Seeing all the best attractions is bound to make you fall in love with Woodsboro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Woodsboro short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Woodsboro?

Yes, there are holiday rentals close to the most popular sights in Woodsboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Woodsboro has to offer?

19th Century Mansion/Farm House: This holiday home rental outside of Woodsboro offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Woodsboro?

While exploring the area, visit family-friendly sights like Catoctin Wildlife Preserve and Zoo, or get outside and enjoy nature at Carroll Creek Linear Park. In the wider area, you’ll find Fort Detrick and Frederick Fairgrounds.

What’s a holiday rental in Woodsboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Woodsboro. Holiday rentals feature amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.

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