Woodsboro Vacation Rentals

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Our top choices for Woodsboro vacation rentals

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
Woodbine
The price is CA $137
CA $203 total
includes taxes & fees
Apr 27 - Apr 28
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

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

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (114 reviews)
"Good stay. Would visit again. "
United States
Lonnie F.
The price is CA $89
CA $256 total
includes taxes & fees
Apr 27 - Apr 28
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Airstream in Wine Country Hot Tub Extra Cost

Airstream in Wine Country Hot Tub Extra Cost
Orrtanna
10.0 out of 10, Exceptional, (96 reviews)
"Place was awesome and very quiet"
United States
Justin L.
Airstream in Wine Country Hot Tub Extra Cost

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (8 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
The price is CA $102
CA $289 total
includes taxes & fees
Apr 27 - Apr 28
Pet-friendly, heart of downtown

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
10.0 out of 10, Exceptional, (26 reviews)
"We had a very nice stay here, kitchen and bathroom had all necessary amenities provided. Cozy cabin, a little chilly at night but blankets were provided as well so it was OK."
United States
Emily Z.
The price is CA $127
CA $200 total
includes taxes & fees
Apr 29 - Apr 30
Birch Cabin at Hunting Creek Hideaway

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Waynesboro
9.8 out of 10, Exceptional, (100 reviews)
"Beautiful location! The host was extremely responsive with any questions most texts were returned within minutes! Will definitely stay here again. "
United States
Michael R.
The price is CA $142
CA $332 total
includes taxes & fees
Apr 27 - Apr 28
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

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

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
9.8 out of 10, Exceptional, (61 reviews)
"The beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
The price is CA $198
CA $430 total
includes taxes & fees
May 3 - May 4
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (143 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is CA $109
CA $320 total
includes taxes & fees
Apr 29 - Apr 30
Charming "Cream of the Crop" Cape ~❤️of Middletown

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (66 reviews)
"Great kitchen, very comfortable beds. Well air conditioned."
United States
Whitney C.
The price is CA $159
CA $358 total
includes taxes & fees
Apr 28 - Apr 29
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Frederick
10.0 out of 10, Exceptional, (8 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is CA $84
CA $284 total
includes taxes & fees
Apr 28 - Apr 29
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (28 reviews)
"Great location, clean place. "
United States
Warren B.
The price is CA $108
CA $294 total
includes taxes & fees
May 6 - May 7
Cozy, dog-friendly, downtown

Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is CA $185
CA $590 total
includes taxes & fees
May 3 - May 4
Rural & Historic Detour Escape w/ Horses On-site!

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (86 reviews)
"Great location and very comfortable. Definitely will consider for future trips to this area."
United States
Jon E.
The price is CA $197
CA $429 total
includes taxes & fees
May 18 - May 19
Luxury Condo In Downtown Frederick

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
9.4 out of 10, Exceptional, (11 reviews)
"Peaceful studio with a lovely view off the porch. Was easy to find and all aspects of the stay were smooth. Perfect place for a few days in Frederick "
United States
Morgan P.
The price is CA $109
CA $232 total
includes taxes & fees
May 4 - May 5
Cozy Pine Tree Nest

New townhouse

New townhouse
Frederick
9.4 out of 10, Exceptional, (10 reviews)
"This property was impeccably clean and so comfortable! The beds were incredibly cozy, and the kitchen was well-stocked. We felt right at home and enjoyed our stay immensely. Beds were comfortable, and kitchen well stocked. The location can't be beat, with so many attractions and wonderful restaurants within a short drive. Tons of nice touches for our arrival; great communication; easy access. We will definitely stay here again!"
United States
Traci U.
The price is CA $207
CA $499 total
includes taxes & fees
Apr 27 - Apr 28
New townhouse

The Gathering Place at Gettysburg. Spacious 4 Bdrm Retreat with deck and grill.

The Gathering Place at Gettysburg. Spacious 4 Bdrm Retreat with deck and grill.
Gettysburg
10.0 out of 10, Exceptional, (5 reviews)
"Very clean home, quiet neighborhood, and close to town. The blueberry muffins were an added delight"
United States
Gail D.
The price is CA $395
CA $628 total
includes taxes & fees
Apr 27 - Apr 28
The Gathering Place at Gettysburg. Spacious 4 Bdrm Retreat with deck and grill.

Gray Getaway

Gray Getaway
Gettysburg Historic District
10.0 out of 10, Exceptional, (1 review)
"Great location, beautiful unit. We really enjoyed our stay "
United States
Kari S.
The price is CA $154
CA $453 total
includes taxes & fees
Apr 27 - Apr 28
Gray Getaway

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (126 reviews)
"The home was a great location to explore downtown Frederick. It had everything that we needed "
United States
David J.
The price is CA $191
CA $430 total
includes taxes & fees
May 17 - May 18
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Spacious 3BR Stay in Westminster | Perfect for Groups & Longer Stays

Spacious 3BR Stay in Westminster | Perfect for Groups & Longer Stays
Westminster
8.0 out of 10, Very good, (5 reviews)
"We enjoyed our stay, spacious rooms and cute decor. "
United States
Anonymous traveller
The price is CA $184
CA $416 total
includes taxes & fees
May 3 - May 4
Spacious 3BR Stay in Westminster | Perfect for Groups & Longer Stays
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Woodsboro?

Yes, we have vacation rentals close to the most popular attractions in Woodsboro, or you can go with a more remote option if you're looking for relaxation.

What are some of the best vacation rentals in Woodsboro?

Thaddeus Stevens' Gettysburg Log Home: This vacation home near Woodsboro offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection 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 larger area, you’ll find Fort Detrick and Frederick Fairgrounds.

What’s a vacation rental in Woodsboro like?

Vacation rentals are privately owned properties you can stay in for short or long periods in Woodsboro. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip.