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Woodsboro Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Woodsboro vacation rentals

A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

1. Rural & Historic Detour Escape w/ Horses On-Site!

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.0 out of 10, Wonderful, (8 reviews)
"Lovely! Our host was gracious and helpful. Property was ideal for our family getaway. i’m"
United States
Mary F.
The price is ￥19,119
￥65,824 total
includes taxes & fees
Nov 13 - Nov 14
Rural & Historic Detour Escape w/ Horses On-Site!
A compact kitchen with a coffee machine, microwave, and a small cart with kitchen tools.

2. 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, (18 reviews)
"Place was perfect and tbe location great. East in and out town..or to get to down town"
United States
Andrew
The price is ￥12,691
￥34,556 total
includes taxes & fees
Nov 22 - Nov 23
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

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

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is ￥25,756
￥68,280 total
includes taxes & fees
Nov 13 - Nov 14
Rural & Historic Detour Escape w/ Horses On-site!
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.2 out of 10, Wonderful, (148 reviews)
"Great location. Amenities were perfect for a little bit of an extended stay. Definitely will come back in the future"
United States
Dave T.
The price is ￥15,801
￥39,695 total
includes taxes & fees
Nov 12 - Nov 13
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

5. 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, (118 reviews)
"Beautiful property! Owner is very quick to communicate and did a fantastic job making it a very relaxing place to stay!"
United States
Cindy B.
The price is ￥13,431
￥33,498 total
includes taxes & fees
Nov 16 - Nov 17
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

6. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (108 reviews)
"Great location"
United States
John
The price is ￥30,148
￥55,238 total
includes taxes & fees
Nov 12 - Nov 13
Modern Condo Right off Market Street
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (162 reviews)
"Great little spot!"
United States
Shelby W.
The price is ￥19,751
￥46,060 total
includes taxes & fees
Nov 15 - Nov 16
Charming "Cream of the Crop" Cape ~❤️of Middletown
A modern kitchen with grey cabinets, a central island, and pendant lighting.

8. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (102 reviews)
"Very convenient location with parking. Prompt communication with owner. However it needs a good deep clean. My towels were used and muddy like the workmen fixing the deck had just showered there. But I would stay there again if necessary."
United States
Jessica
The price is ￥25,455
￥52,609 total
includes taxes & fees
Nov 11 - Nov 12
Luxury Condo In Downtown Frederick
A kitchen with a dishwasher, a sink, and a stove. There are pots hanging above the sink and a window with a view of greenery outside.

9. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (72 reviews)
"The house is very cute and a perfect fit for our needs. We appreciated how clean the house was too! It's conveniently located to some many restaurants and shops. We would gladly stay here again!"
United States
Sara W.
The price is ￥22,654
￥44,112 total
includes taxes & fees
Nov 17 - Nov 18
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A brick building with a waterfall feature in front.

10. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (13 reviews)
"We had a great time. It was perfect for us. I would highly recommend it to others and would not hesitate to return there when back in the area. "
United States
Tereasa G.
The price is ￥27,446
￥60,916 total
includes taxes & fees
Nov 16 - Nov 17
New townhouse
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

11. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (22 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
United States
Janice M.
The price is ￥33,656
￥74,533 total
includes taxes & fees
Nov 12 - Nov 13
Newly constructed 6 bedroom home
A house with a covered porch, two wicker chairs, a welcome sign, and a hanging flower basket.

12. Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
Blue Ridge Summit
9.6 out of 10, Exceptional, (21 reviews)
"Great spot close to the wedding venue!!"
United States
Alfred T.
The price is ￥9,670
￥26,775 total
includes taxes & fees
Dec 6 - Dec 7
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
A rustic, cylindrical structure with a thatched roof, a small seating area, and a view of the surrounding forest.

13. Bin There Treehouse - A Grain Bin treehouse!

Bin There Treehouse - A Grain Bin treehouse!
Washington County
9.8 out of 10, Exceptional, (6 reviews)
"Such a neat place! Very peaceful setting."
United States
Abby G.
The price is ￥22,896
￥31,729 total
includes taxes & fees
Nov 12 - Nov 13
Bin There Treehouse - A Grain Bin treehouse!
A log cabin interior with a wooden bench, a leather sofa, a coffee table, and a bookshelf.

14. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is ￥30,022
￥34,503 total
includes taxes & fees
Nov 25 - Nov 26
Cozy Downtown Cabin - Family Friendly
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

15. 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
10.0 out of 10, Exceptional, (75 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is ￥13,431
￥36,346 total
includes taxes & fees
Nov 11 - Nov 12
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A bathroom with a towel rack, a mirror, a sink, and a potted plant.

16. Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Highfield-Cascade
10.0 out of 10, Exceptional, (11 reviews)
"I cannot say enough about the wonderful time we had staying at Denise & Mike's lovely cottage. They went above and beyond to make sure our family gathering was perfect...and it truly was. Sitting on the front porch sharing coffee in the a.m. and wine in the evening. Board games, chats and laughter until our bellies ached. Our family spent our much needed reunion sharing long overdue times making more wonderful memories. Upon arrival we found the property even more special than we imagined from...
United States
Julianne L.
The price is ￥17,492
￥38,138 total
includes taxes & fees
Nov 11 - Nov 12
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
A lakeside setting with wooden chairs and a picnic table, surrounded by lush greenery and trees.

17. 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, (110 reviews)
"This was our 4th stay and enjoyed every one!"
United States
Anonymous traveler
The price is ￥12,678
￥34,016 total
includes taxes & fees
Nov 12 - Nov 13
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
A corner room with a sliding glass door closet, a wooden cabinet with glass doors, and a small rug on the floor.

18. Private Sauna, Fireplace and Country Views

Private Sauna, Fireplace and Country Views
Mount Airy
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful location with a beautiful field where wild animals visited. Hosts really took care of the amenities (great coffee bar). Close to Mt Airy and vineyards."
United States
Richard B.
The price is ￥54,676
￥62,492 total
includes taxes & fees
Nov 18 - Nov 19
Private Sauna, Fireplace and Country Views
A ping pong table in a room with a television, a plant, and a sofa.

19. 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
8.0 out of 10, Very good, (2 reviews)
"The stay was at a beautiful new home. Great host. Location close to Interstate 70. I had everything I needed. Took in the sights in DC via the Greenline Metro. I would definitely stay here again."
United States
Scott C.
The price is ￥16,275
￥22,611 total
includes taxes & fees
Nov 15 - Nov 16
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
A spacious room with large windows, a ceiling fan, and a modern chair.

20. Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Fairfield
9.8 out of 10, Exceptional, (52 reviews)
"Awesome place."
United States
Holly J.
The price is ￥63,204
￥94,547 total
includes taxes & fees
Nov 11 - Nov 12
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from 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.
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Top Woodsboro Hotel Reviews

Budget Host Three Crowns Motor Lodge

Budget Host Three Crowns Motor Lodge

8/10 Good
"Decent room across the street from the National Cemetery. Walking distance to many restaurants and Civil War sights"
Ray 1-night trip
Posted less than an hour ago
Budget Host Three Crowns Motor Lodge

Find out more about Woodsboro

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Look no further and take a look at our great range of rental properties in Woodsboro!

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?

Unique Gettysburg Barn Loft central to Gettysburg and Ski Liberty!: This vacation home near Woodsboro offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so 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 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.