Woodsboro Holiday Rentals

    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

This weekend
Next weekend

Holiday Rentals in Woodsboro

Apple Blossom Cottage! HT Extra Cost

10.0 out of 10, Exceptional, (304)
"Was quite and peaceful had everything you needed not far from town "
The price is NZ$379
includes taxes & fees
10 July - 11 July
Apple Blossom Cottage! HT Extra Cost

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

9.6 out of 10, Exceptional, (98)
"It was just wonderful. Totally charming "
The price is NZ$297
includes taxes & fees
8 July - 9 July
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (105)
"Traveled from Baltimore to get away for a few days. Great location and mountain views. Cozy vintage cabin nicely renovated. "
Countryside Cabin with Mountain Views near Surreybrooke Gardens

Beautiful Mansion in the Country & Wedding Venue

9.8 out of 10, Exceptional, (9)
"The stay and place was awesome and my family and I will definitely be booking again "
The price is NZ$3,911
includes taxes & fees
8 July - 9 July
Beautiful Mansion in the Country & Wedding Venue

Creekside Cabin at Gettysburg

10.0 out of 10, Exceptional, (167)
"This historic cabin is in a wooded setting with deer a creek and bird songs. The amenities all worked to make a comfortable stay. Great access to museums, antiques, hiking, and scenic drives."
Creekside Cabin at Gettysburg

Round Top Campground

2.0 star property
9.2 out of 10, Wonderful, (17)
"Cabin was nice and convenient, the showers and grounds has some great stuff to do for kids and families, gift shop is nice, staff was fantastic, ants became an issue they were all over the sink, counters and even in the bed rooms, that was the only issue, besides that everything was great"
Round Top Campground

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

The price is NZ$799
includes taxes & fees
14 July - 15 July
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Birch Cabin at Hunting Creek Hideaway

9.6 out of 10, Exceptional, (4)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
The price is NZ$245
includes taxes & fees
10 July - 11 July
Birch Cabin at Hunting Creek Hideaway

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

10.0 out of 10, Exceptional, (102)
"Had originally planned on staying with a buddy of mine from the service, he got sick and couldn't make it so I stayed there alone. Plenty to do and see in Gettysburg, the location was within walking distance of the town center. "
Belle on Buford<br>Apt 1-1st Floor

Exquisite, first floor stone ranch Gettysburg large kitchen/living area - quiet

10.0 out of 10, Exceptional, (83)
"This is a gorgeous, spacious home within minutes of downtown Gettysburg. It was a great location where we could come back after our day of adventure and not feel like we would be tripping over each other. If I am ever in Gettysburg again, I will definitely consider staying here again."
Exquisite, first floor stone ranch Gettysburg large kitchen/living area - quiet

Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

9.4 out of 10, Exceptional, (220)
"Good stay over all - everything you could ever need and great views from the bedroom!"
Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

Downtown location w/ parking. Transit stop across the street. Unit 2 of 4.

9.4 out of 10, Exceptional, (92)
"Very close to the Gettysburg National Military Park"
Downtown location w/ parking. Transit stop across the street. Unit 2 of 4.

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

9.8 out of 10, Exceptional, (49)
"Visiting family over the holidays. Our trip was great. Location was perfect. Rental house accommodations fulfilled our needs, was clean and had everything we needed. Will definitely stay again. "
The price is NZ$406
includes taxes & fees
8 July - 9 July
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

3-bedroom cabin in a wooded setting just 17 minutes from Gettysburg

10.0 out of 10, Exceptional, (300)
"We've stayed here multiple times and always have a great time. Very close to Liberty for skiing. Always good communication with the owner and the cabin is cozy and well-stocked. Highly recommend!"
3-bedroom cabin in a wooded setting just 17 minutes from Gettysburg

Scenic Mountaintop Villa with Free WiFi & Pool

6.8 out of 10, (5)
"Very nice "
Scenic Mountaintop Villa with Free WiFi & Pool

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

9.4 out of 10, Exceptional, (100)
"It is a lovely home and we had a lovely time"
The price is NZ$462
includes taxes & fees
11 July - 12 July
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (137)
"Charming, nicely restored log home in a great location for downtown. We would definitely stay here again! "
Gorgeous 1840 Log Cabin- Downtown

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (44)
"Great stay! "
The price is NZ$459
includes taxes & fees
15 July - 16 July
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Unique Gettysburg Barn Loft central to Gettysburg and Ski Liberty!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Lots of room, great location. Owner was quick to answer any questions we had."
Unique Gettysburg Barn Loft central to Gettysburg and Ski Liberty!

Manor on the 7th Luxury minutes away from History

10.0 out of 10, Exceptional, (13)
"The house, property, and overall experience were top notch. Highly recommend. "
Manor on the 7th Luxury minutes away from History
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

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’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.