Woodsboro Holiday Rentals

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Holiday Rentals in Woodsboro

Think Snow! Liberty Ski Resort 5 minutes Away! Time to plan a winter getaway!

Fairfield
10.0 out of 10, Exceptional, (311)
"Very clean and was perfect location for our golf weekend ! Thanks again … "
United States
jim h.
Think Snow! Liberty Ski Resort 5 minutes Away! Time to plan a winter getaway!

Countryside Cabin with Mountain Views near Surreybrooke Gardens

Middletown
10.0 out of 10, Exceptional, (127)
"Great location. Very quick responses to texts. Susan checked in every day."
United States
Diane M.
Countryside Cabin with Mountain Views near Surreybrooke Gardens

1852 Historic Stone home

Gettysburg Historic District
10.0 out of 10, Exceptional, (145)
"Perfect! Clean, spacious, stylish, comfortable and fabulous location! "
United States
Janine Y.
The price is AU$901
includes taxes & fees
16 Dec - 17 Dec
1852 Historic Stone home

Apple Blossom Cottage! HT Extra Cost

Orrtanna
9.8 out of 10, Exceptional, (322)
"We loved our stay at the Apple Blossom Cottage. It was very cozy and clean with loads of charm. There is a lot of thoughtful touches that makes you want come back again and again. It’s a great romantic getaway!!"
United States
Carolyn P.
Apple Blossom Cottage! HT Extra Cost

Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

Fairfield
9.6 out of 10, Exceptional, (239)
"Great Stay ! We had everything we needed. So relaxing and would love to stay again."
United States
Kathy S.
Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

IDEAL LOCATION DOWNTOWN-groups&families! Living rooms on 3 levels-ADA accessible

Gettysburg Historic District
10.0 out of 10, Exceptional, (75)
"Had everything we needed!"
United States
Dana S.
IDEAL LOCATION DOWNTOWN-groups&families! Living rooms on 3 levels-ADA accessible

Sprawling 9‑BR Mountaintop Oasis- BlueRidge Views

Waynesboro
Sprawling 9‑BR Mountaintop Oasis- BlueRidge Views

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Downtown Frederick
9.4 out of 10, Exceptional, (118)
"We enjoyed our stay here. It was a great location, well restored, and very clean."
United States
Meagan P.
The price is AU$447
includes taxes & fees
18 Nov - 19 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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

Middletown
9.6 out of 10, Exceptional, (104)
"Very cute cottage, filled with rustic charm. Convenient to hiking in Catoctin and restaurants in Frederick. AC worked great on a hot weekend! No door on the bathroom, just a curtain, FYI!"
United States
Cate O.
The price is AU$297
includes taxes & fees
16 Nov - 17 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Beautiful Mansion in the Country & Wedding Venue

Waynesboro
9.8 out of 10, Exceptional, (9)
"The stay and place was awesome and my family and I will definitely be booking again "
United States
Comedy C.
The price is AU$4,107
includes taxes & fees
17 Nov - 18 Nov
Beautiful Mansion in the Country & Wedding Venue

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

Middletown
10.0 out of 10, Exceptional, (139)
"Lovely home Centrally located to explore historic sites/ towns Very quiet little town "
United States
M Theresa B.
The price is AU$434
includes taxes & fees
16 Nov - 17 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown

Birch Cabin at Hunting Creek Hideaway

Thurmont
9.8 out of 10, Exceptional, (16)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
United States
Julie B.
The price is AU$215
includes taxes & fees
18 Nov - 19 Nov
Birch Cabin at Hunting Creek Hideaway

ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !

Frederick
10.0 out of 10, Exceptional, (145)
"We had a wonderful stay! Deb provided very thorough instructions and information about the area, was very responsive, and the house was just lovely. Easy check in and check out, with *no* list of cleaning or other check out requirements. The pool is fantastic, with a great covered patio for those not in the pool. Well supplied kitchen, and plenty of bath towels and toiletries. All in all, one of our favorite stays!"
United States
Jennifer S.
The price is AU$647
includes taxes & fees
16 Nov - 17 Nov
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !

Manor on the 7th Luxury minutes away from History

Gettysburg
9.8 out of 10, Exceptional, (17)
"Amazing house, very well kept, spacious and had all of the amenities we were looking for."
United States
Ryan C.
Manor on the 7th Luxury minutes away from History

Gettysburg Home sleeps 10 with parking and Game Room. Just off the square.

Gettysburg
9.2 out of 10, Wonderful, (20)
"Our party of ten stayed for a single night to spend a couple of days in Gettysburg. The house is a little less than half a mile to the center of town, very easy to walk. We had a large 12 person van and had no difficulty parking this in the lot adjacent to the house.The house is charming and very spacious. "
United States
John B.
The price is AU$949
includes taxes & fees
17 Nov - 18 Nov
Gettysburg Home sleeps 10 with parking and Game Room. Just off the square.

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Frederick
10.0 out of 10, Exceptional, (33)
"Great location, comfortable and attractive space. We enjoyed the visit."
United States
claire e.
The price is AU$387
includes taxes & fees
16 Nov - 17 Nov
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Scenic Mountaintop Villa with Free WiFi & Pool

Waynesboro
6.8 out of 10, (5)
"First of all, we booked this place because we were a group of families with small children and we wanted a place with swimming pool and a large indoor space. When my friends reached there, they asked my friends to stay at a different place and later on asked to move to this house, when were all settled in. We waited for hours to check in. After checking into this place,there’s no tv, no WiFi and there’s problem with shower. This place needs a major renovation. I tried to contact the host, but...
United States
Tee T.
Scenic Mountaintop Villa with Free WiFi & Pool

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

Rohrersville
10.0 out of 10, Exceptional, (6)
"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. "
United States
Christopher R.
The price is AU$656
includes taxes & fees
25 Nov - 26 Nov
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Perfect Location: Historic Downtown Guesthouse

Gettysburg Historic District
9.8 out of 10, Exceptional, (259)
"The property was very clean, located right downtown, and had off street parking for all of our bikes. "
United States
Cory P.
Perfect Location: Historic Downtown Guesthouse

Airstream in Wine Country Hot Tub Extra Cost

Orrtanna
10.0 out of 10, Exceptional, (90)
"We stayed for three nights and every night was just better and better. Secluded location yet still close to go to the battlefield. Great hot tub and the airstream was awesome! The host was great too! We only "
United States
Nick S.
Airstream in Wine Country Hot Tub Extra Cost
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

Find out more about Woodsboro

Everything you need to know about Woodsboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodsboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodsboro holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Woodsboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodsboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodsboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodsboro holiday rentals we have selected for you start as low as AU$215 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Woodsboro rentals

At Expedia, we put the best Woodsboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Woodsboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodsboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodsboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

1852 Historic Stone home: This holiday home rental outside of Woodsboro is located in the city centre, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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.