Holiday houses in Woodsboro

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Top-rated holiday rentals in Woodsboro

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Guest favourite
The studio apartment showcases a compact layout with a modern kitchenette equipped with stainless steel appliances. A cozy sleeping area features a spacious bed adorned with soft linens. A wooden dining table with black stools is positioned nearby, creating a welcoming space for dining.
Apartment in Frederick
4.89 out of 5 average rating, 380 reviews

Downtown Frederick Modern Studio

Modern 1-bedroom studio apartment located on North Market Street (NOMA) in charming downtown Frederick. Walking distance to great restaurants, shops, breweries and nightlife. Studio includes a full kitchen and luxurious bathroom providing everything you need to enjoy your time in downtown Frederick. Conveniently located behind laundromat (Noma Laundry) which is open from 5AM-11PM. 5 minute walk to the heart of Frederick and minutes away from Gravel & Grind coffee cafe and Olde Mother brewery.

Top Guest favourite
A stylish living area combines a modern yellow armchair and a dark gray sectional sofa, positioned around a glass coffee table. Light-colored curtains frame two windows, allowing natural light to fill the space. A piece of wall art adds a pop of color to the neutral walls.
Apartment in Downtown Frederick
5 out of 5 average rating, 41 reviews

Brent House | Downtown Frederick

Welcome to Brent House on 4th in beautiful Historic Downtown Frederick, Maryland. Enjoy a stylish and inspiring experience at our centrally-located dog-friendly flat in the heart of Downtown. Relax on our roof top deck after a day discovering why Frederick has been named one of the coolest places to visit with restaurants, wineries, breweries, art, recreation and more just steps from our location. The flat has a spacious living room, an eat-in kitchenette, a large bedroom, parking included.

Top Guest favourite
A spacious living area features a pool table centered on a patterned rug. Comfortable seating options surround the space, with light-colored walls complementing the decorative elements. A tall plant adds a touch of greenery, while various artwork adorns the walls, contributing to a welcoming environment.
Condo in Frederick
4.96 out of 5 average rating, 126 reviews

2 Queen & 1 Twin Bed / Mountain & Museum Fun

Perched well above the city and in between Gambrill State Park and Cunningham Falls State Park, enjoy your stay in this extra large living space. Fifteen minutes from the city limits of Frederick, come and enjoy the peaceful surroundings with all the amenities of modern life. Bring your bikes and hiking boots to experience the myriad of trails and wildlife throughout the region. Close to the quaint City of Frederick. Dozens of wineries, craft breweries, and antique stores located nearby.

Top Guest favourite
The exterior of a two-story house is surrounded by trees, with warm lights framing the balconies. Large glass windows provide visibility into the interior. A deck with a railing is seen above, and decorative elements are positioned outside the entrance.
Guest suite in Smithsburg
4.98 out of 5 average rating, 317 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Top Guest favourite
A stone rancher is shown with a neatly manicured lawn and landscaping. The covered front porch displays decorative railings and a light fixture. Windows allow natural light into the home. A macadam driveway leads to a two-car garage on the right side.
Home in Keymar
4.95 out of 5 average rating, 55 reviews

Keymar Cottage

Stay in this stone rancher in beautiful rural Frederick County half an hour from historic Gettysburg and Frederick. The property is surrounded by fields on three sides with a great view of the mountains (unless the corn is too tall). Watch the sunrise from the front porch and sit on the back patio to watch the sunset. There is a two-car garage and a macadam driveway for parking. The six-tenths acre property includes a nice grassy lawn, trees and shrubbery and a picnic table on the patio.

Top Guest favourite
A two-story cottage is set amidst lush greenery, featuring a large upper deck that offers views of the surrounding woods. Colorful azaleas and shrubs enhance the entrance, while a gravel drive leads to the property, surrounded by trees exhibiting signs of spring.
Guesthouse in Myersville
4.94 out of 5 average rating, 257 reviews

Spruce Run Cottage, Farm stay on Catoctin Mountain

The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

Superhost
Cabin in Thurmont
5 out of 5 average rating, 4 reviews

Basecamp Frederick Cabin - Mountain Stay

Rest, relax, and explore the outdoors at our quaint, charming log cabin in the Mountaindale Historical District near the Frederick Municipal Forest & Watershed. Basecamp Frederick Cabin is a semi-rustic retreat for outdoor lovers interested in coming to the area for peace and a little slice of nature. It’s the perfect area for couples, small families, and friends looking to spend a relaxing few days in the mountains. NOTE: This is in a quiet, residential community.

Top Guest favourite
The exterior of a colonial era spring house showcases a natural stone base supporting a wooden structure. A spacious balcony with wooden railings extends from the second floor. Brightly colored hanging flower pots add a touch of greenery to the inviting façade.
Home in Blue Ridge Summit
4.99 out of 5 average rating, 608 reviews

Colonial Era Spring House

A unique and private mountain top colonial era spring house, with two springs flowing thru the basement. Originally the site of a tannery in the 1700s. Here you can relax, recharge, and rejuvenate. We celebrate all four seasons where you can enjoy Mother Nature's ever changing scenery at 1300' above sea level with fresh mountain air. Our area offers many things to do, or you may choose to stay in and do nothing at all.

Top Guest favourite
A cozy living area features a gray sofa with a yellow throw pillow, set against a dark blue wall. A small dining table with chairs is situated by the window, allowing natural light to illuminate the room. The kitchen area is partially visible, showcasing modern appliances.
Loft in Frederick
4.96 out of 5 average rating, 192 reviews

Free Parking, Dogs • Walk to Breweries & Coffee

This charming downtown Frederick flat is made for foodies, coffee lovers, and city explorers. Just steps from Frederick’s top breweries and cafés, it’s the perfect home base for a weekend getaway with your pup. With pet amenities, local recs, parking, and fast Wi-Fi, it’s both fun and functional. Free parking in a dedicated spot on a gravel lot behind the home, which is a 2 minute walk to the front door.

Top Guest favourite
A two-story town home displays a welcoming exterior, featuring a light-colored facade and dual garage doors. A spacious driveway provides ample parking space, framed by neatly landscaped areas and patches of green grass. Scenic farmland can be seen beyond the property.
Guesthouse in Frederick
5 out of 5 average rating, 107 reviews

A Quiet Haven

A town-house size in-law suite/ 2 floors. Private entrance...in a development. Quiet area. 20 min from Frederick, MD or 1 hour to D C or Baltimore or 45 min to Gettysburg or to Fairfield, PA for skiing. Private entrance with farmland scenery out back of townhouse. Parking space for 2 cars. NO PETS facility but Several kennels nearby. Please No Smoking allowed inside.. may use bench out front.

Top Guest favourite
The exterior of a townhouse is shown, featuring a light brown facade with red shutters and a copper-colored awning above the front door. A walkway leads to the entrance, flanked by landscaped areas and greenery. A playground can be seen in the background.
Townhouse in Frederick
4.97 out of 5 average rating, 68 reviews

Spacious & Charming Private Basement Apt

Forget your worries in this spacious and unique basement space. Nestled in the serene Ballenger Creek section of Frederick, this charming, spacious, and private entrance basement apartment offers a delightful retreat for up to 4 guests. Designed with your comfort and convenience in mind, this above-ground haven is the perfect blend of homeliness and modern amenities, ensuring a memorable stay.

Top Guest favourite
A cozy living area features two windows allowing natural light to enter. A dark sofa complements a round coffee table in the center. Floral accent chairs add a touch of color, while soft drapes frame the windows, creating a serene ambiance.
Townhouse in Frederick
4.97 out of 5 average rating, 34 reviews

Spacious 1 Bed House, Close to Downtown Frederick

Come relax in this beautiful home away from home, located in a very clean & peaceful community. 1 bedroom master suite includes a stand up shower, soak in tube, sitting area and a walk-in closet. Located minutes away from downtown frederick and very close to many shopping stores. Highspeed internet/wifi and Smart TV access in all rooms (bedrooms included).

Popular amenities for Woodsboro holiday rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Frederick County
  5. Woodsboro