Woodsboro Holiday Rentals

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Holiday Rentals in Woodsboro

Creekside Cabin at Gettysburg

10.0 out of 10, Exceptional, (172)
"We loved the charming cabin, which was perfect for the four of us. The two bathrooms was a great convenience. Although our busy weekend schedule meant we didn’t spend much time there, we will definitely be back. We also enjoyed meeting Tami and her granddaughter; she was a great host. "
Creekside Cabin at Gettysburg

Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort

10.0 out of 10, Exceptional, (15)
"The cabin was amazing and relaxing. I especially enjoyed the babbling brook in the morning while sipping my coffee on the deck—great for pet-friendly families."
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort

Apple Blossom Cottage! HT Extra Cost

10.0 out of 10, Exceptional, (306)
"We had a couple of minor issues which were resolved within 6 hours. Cute little cottage close (10 to 20 minutes) to most sights in Gettysburg. Hot tub not being clean and a couple of ants in the cottage are the only reasons that it was a 4 out of 5."
Apple Blossom Cottage! HT Extra Cost

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 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 AU$3,931
includes taxes & fees
8 Aug - 9 Aug
Beautiful Mansion in the Country & Wedding Venue

Scenic Mountaintop Villa with Free WiFi & Pool

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

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

9.6 out of 10, Exceptional, (99)
"Our weekend cabin stay was wonderful. The safe neighborhood was quite and peaceful. Its location near nature and the city was just perfect. The cozy cabin was clean and comfy. We loved Gambrill State Park and downtown Frederick didn't disappoint as well."
The price is AU$298
includes taxes & fees
7 Aug - 8 Aug
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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

10.0 out of 10, Exceptional, (1)
"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 AU$754
includes taxes & fees
13 Aug - 14 Aug
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

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

10.0 out of 10, Exceptional, (88)
"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

Historic Boonsboro Vacation Rental w/ Grill

9.2 out of 10, Wonderful, (15)
"It was perfect. Near my son’s school at Shepherd University and close to all the historic sites of Harper’s Ferry and Antietam."
Historic Boonsboro Vacation Rental w/ Grill

Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

10.0 out of 10, Exceptional, (3)
"Very nice place .Quiet and peaceful"
The price is AU$374
includes taxes & fees
5 Aug - 6 Aug
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

Cozy Loft Retreat- Walk to Liberty Mountain Resort

10.0 out of 10, Exceptional, (3)
"Cozy, cute and comfortable - had everything we needed for a short stay."
The price is AU$334
includes taxes & fees
24 Aug - 25 Aug
Cozy Loft Retreat- Walk to Liberty Mountain Resort

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!

Lincoln Quarters, 2nd floor, Only 2 blocks to the center of town.

10.0 out of 10, Exceptional, (127)
"All was wonderful, enjoyed our stay. "
Lincoln Quarters, 2nd floor, Only 2 blocks to the center of town.

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (108)
"Beautiful location with some of the most immaculately cared for grounds I’ve ever seen!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens

Charming Apartment in the Heart of Gettysburg!

9.8 out of 10, Exceptional, (150)
"Apartment was perfect for the two of us. "
Charming Apartment in the Heart of Gettysburg!

*Modern Condo In Downtown Frederick*

9.4 out of 10, Exceptional, (65)
"Great stay "
The price is AU$489
includes taxes & fees
26 Aug - 27 Aug
*Modern Condo In Downtown Frederick*

Misty Mountain Lodge Pickleball Liberty Ski

10.0 out of 10, Exceptional, (20)
"Great location, we lucked out and had a snow-filled weekend. Perfect secluded spot to take it all in!"
The price is AU$1,773
includes taxes & fees
4 Aug - 5 Aug
Misty Mountain Lodge Pickleball Liberty Ski

1852 Historic Stone home

10.0 out of 10, Exceptional, (130)
"This property was AMAZING. easiest time staying at a home I've ever had. Loved the location and the entire house has been done so well."
The price is AU$917
includes taxes & fees
20 Aug - 21 Aug
1852 Historic Stone home

“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
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 Woodsboro Hotel Reviews

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.