Vacation rentals in Jefferson

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Top-rated vacation rentals in Jefferson

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Top guest favorite

The exterior of a ranch-style house is visible, featuring a light-colored facade and a red roof. A covered carport is seen on the right. Lush green grass and shrubbery frame the front, while trees and a clear blue sky are visible in the background.

Home in Middletown

5 out of 5 average rating, 9 reviews

Spacious Frederick Cty Retreat

Forget your worries in this spacious and serene space. One street over from Main St in Middletown, MD. 15 minutes to the heart of Frederick. We are within walking distance of Main Cup, Brew 30, Tapias, Moore's Icecream and Subway. Fratelli's, Black Hog, Baskin Robins, Dunkin Donuts and Cinco De Mayo are within a mile. Safeway grocery is a mile away. Near many parks, hiking trails and battle fields. Less than 20 minutes to Hagerstown, MD. Our street is safe with sidewalks to walk on. Wildlife too

Top guest favorite

A bright and airy loft apartment features a queen bed with a patterned coverlet. A cozy sofa is present, complemented by a small side table. The fully equipped kitchen is visible, along with a dining area set for four and a smart TV mounted on the wall.

Loft in Brunswick

4.94 out of 5 average rating, 226 reviews

Loft Apt Just off C&O near Harpers Ferry and AT

This beautiful loft apartment is right in the center of downtown Brunswick! The apartment offers a queen bed on the main floor and two twin beds in the loft. There is a small section sofa that can be used for an additional sleeping space. The apartment offers a fully equipped kitchen with a stove, oven, microwave and refrigerator along with a washer and dryer. There is wifi and a Smart TV, which is on a swivel mount so you can watch your favorite streaming services from the couch or the bed.

Guest favorite

The image features a wide view of a historic farm, highlighting a modern, renovated Milk House structure and a large barn with a metal roof. Green fields and a gravel path surrounding the buildings contribute to the tranquil rural setting, with distant hills under a partly cloudy sky.

Farm stay in Middletown

4.94 out of 5 average rating, 51 reviews

The Milk House at Hereford Grove Farm

The Milk House at Hereford Grove Farm is a completely renovated efficiency space located on a beautiful, 128 acre, historic farm. All facilities are brand new and modern. Come experience the magic of this unique and tranquil getaway for two. The pastoral setting includes breathtaking views and sunsets, beautiful barns, a spring-fed pond, and nearby grazing cattle. The farm is a great setting for pets. Due to the size of the Milk House, only one pet is allowed and no cats are permitted.

Guest favorite

The charming exterior of the restored farmhouse features a welcoming front porch adorned with seating, inviting guests to relax. The façade is complemented by traditional shutters and clean lines, while an American flag adds a touch of local character.

Home in Jefferson

4.93 out of 5 average rating, 258 reviews

"Rusty Rose" ~ Restored farmhouse 🖤 of Jefferson

"Rusty Rose~amazing restored Farmhouse located in the heart of Jefferson. The perfect combination of "Leather & Lace"~ restoration met renovation to offer a unique property like no other to guests. Set your sights on adventure! Downtown Frederick restaurants, shops, parks, & nightlife. VA, MD, & WV local wineries & breweries. Hike the Appalachian trail. Float the Potomac River. Bike the C&O Canal. Ski the slopes. Golf 18 holes. Go antiquing. Tour quaint nearby towns restaurants & shops.

Top guest favorite

A charming early 19th century farmhouse is shown, featuring a large front porch with a wooden railing. The white exterior contrasts with the natural greenery surrounding the house, while a manicured lawn extends in front. The structure is complemented by a sturdy stone foundation.

Home in Jefferson

4.85 out of 5 average rating, 210 reviews

Chestnut House at Fox Haven Farm

Beautiful countryside vistas, nature-lover's paradise, feels like you are far away, yet the fine food and art of Frederick are only a 15 minute drive up the road. Hikes, Harper's Ferry, Ski Liberty, or just the quiet of our bucolic setting await. It can also be a part of a larger retreat when combined with 2 other farmhouses on the farm, and a restored Dairy Parlor venue. It's a great place to host friends, family, and more. You can join one of our farm-based education classes too.

Guest favorite

A large outdoor space features a circle of brightly colored chairs arranged around a stone fire pit. Lush green grass surrounds the area, complemented by tall trees. In the background, a historic farmhouse with a red exterior and a white roof is visible.

Home in Jefferson

4.94 out of 5 average rating, 51 reviews

Firefly Hill Farmhouse

This historic farmhouse has space for everyone, even the pups! The house was built in 1873 and owned by the same family for five generations. Newly renovated, its situated on a former working farm adjacent to a small historic town. There are many attractions in short driving distance and parks & eateries in walking distance. A large yard with a fire pit, grill, and hammock are part of the property. Close to Frederick, Washington, D.C., Harpers Ferry, Antietam, and South Mountain.

Guest favorite

A serene countryside view showcases a spacious green lawn bordered by trees and hills in the background. Two houses are visible: one with a wraparound porch and the other a smaller structure. An organic garden is seen in the foreground, framed by a simple fence.

Guesthouse in Keedysville

4.97 out of 5 average rating, 224 reviews

City Dog Farm

Comfortable, light-filled one bedroom apartment on 10 acres in Maryland near Antietam battlefield and Harpers Ferry, WV. We have chickens, an organic garden, hills, woods and a stream. Apartment is 15 minutes from Harpers Ferry, Antietam battlefield, the C&O canal, river rafting on the Potomac or Shenandoah, vineyards, the Appalachian trail and small towns including Boonsboro and Shepherdstown, WV. 30 minutes to Frederick or Hagerstown/1.5 hours to DC or Baltimore. SORRY NO PETS

Top guest favorite

Lush greenery dominates the foreground, leading to a panoramic view of the distant landscape. A small structure with a white roof sits among the trees, while expansive blue skies are scattered with white clouds, enhancing the natural setting.

Guesthouse in Frederick

4.98 out of 5 average rating, 42 reviews

Boutique space at Marble Ridge

Boutique accommodations are defined as a unique and luxurious space~and that is what you will find here at Marble Ridge. The private entrance opens up to a living space that is comfortably modern with clean lines. The large picture windows allow tons of natural light and a spectacular view. You will have all the amenities available to you such as a full kitchen with refrigerator/freezer, stove/oven, microwave, coffee maker, dishwasher, WiFi, TV, fireplace, private full bath.

Guest favorite

The exterior of a renovated mobile home showcases a colorful façade with horizontal stripes of orange, yellow, and white. Lush greenery surrounds the home, with a well-maintained lawn and coniferous trees providing a natural backdrop. A shed is visible alongside the mobile home.

Place to stay in Middletown

4.87 out of 5 average rating, 53 reviews

Vintage Mobile Home and Storage Workshop

Renovated in 2021, this 1960's era mobile home has character that will make you smile! Includes WiFi, one bedroom with a queen bed, full bathroom, walk-in closet, full kitchen, and front porch. Guests have access to a large funky workshop for large storage needs (kayaks, bicycles, skis, snowboards, fishing gear, etc.). This rare gem is nicknamed "Don't Stop Believing" because even though it is a bit aged, it holds on to the ability to provide you with a home away from home!

Guest favorite

The bedroom features a spacious queen bed with a light-colored quilt and decorative pillows. A green accent chair is positioned at the foot of the bed. Natural light enters through a large sliding door, complemented by soft curtains. Wall art adds a calming touch.

Home in Frederick

4.83 out of 5 average rating, 94 reviews

Spacious Private Basement Apartment

You and your loved ones will be comfortable in this spacious and unique private basement apartment. 910 sq/ft. Beautifully decorated. Braddock heights area, less than half a mile to I 70, 3 miles to I 270 and two miles to route 340. Restaurants and shopping plazas, less than 6 miles to Downtown Frederick. There are many attractions around such as local breweries, parks, museums and more. Private entrance with 1 parking spot on the premisses. Huge backyard and patio.

Top guest favorite

Delicate white flowers bloom on branches, contrasting with the brown siding of the historic house. The background reveals a green door and two windows, allowing glimpses of the home’s rustic charm. The scene captures the tranquility of the surroundings, marked by budding magnolia blossoms.

Apartment in Burkittsville

4.98 out of 5 average rating, 124 reviews

Charming Burkittsville 1747 Home

Studio apartment located in the rural historic town of Burkittsville MD (Est. 1824) at the base of South Mountain, surrounded by beautiful farmland. About 25 minutes to Antietam battlefield, Harpers Ferry WV, Shepherdstown WV, Middletown MD, Frederick MD. Close to many activities including wineries, breweries, award winning restaurants, theater, hiking, biking, river activities, Appalachian trail, C&O canal, national and state parks.

Top guest favorite

The exterior of a two-story carriage home is displayed, featuring a sloped roof and prominent front porch. A manicured lawn surrounds the structure, with evergreen shrubs and small trees in the background. The driveway leads to a spacious path, enhancing accessibility.

Guest suite in Frederick

4.93 out of 5 average rating, 123 reviews

Spacious Carriage Home Suite in Frederick MD

NEAR HISTORIC DOWNTOWN FREDERICK - Super Spacious 2nd Floor Guest Home Suite located on 5 Acres with an amazing view! Freshly painted and newly furnished with fresh appliances. Long Driveway entrance with plenty of parking available. Only 46 miles from Baltimore and 50 miles away from D.C. Downtown Frederick is only a couple of minutes away so you can enjoy shopping, restaurants, and experience everything Frederick has to offer!