Vacation rentals in Jefferson

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Top-rated vacation rentals in Jefferson

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

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

Spacious Private cozy apartment near mountains

Unwind in a spacious, private basement apartment in Braddock Heights, ideal for couples, small families, or remote stays. This 910 sq ft retreat features a private entrance, open layout, comfortable living area, bedroom, full bath, and kitchenette. Conveniently located minutes from downtown Frederick and major routes, yet tucked in a quiet area near hiking trails and wineries. Enjoy the large backyard with patio and fire pit. Includes one dedicated parking space. A peaceful and comfortable place

4.85 out of 5 average rating, 148 reviews

Guest favourite

Guest suite in Middletown

Cozy Farmhouse Guest Suite w/ Private Deck

Imagine soaking some sunshine from the private deck of a lovingly renovated 1800s farmhouse. On warm days dip into one of the two creeks bordering the 25-acre farm; in cooler seasons, enjoy peaceful walks under open skies. This private guest suite with bedroom, bath, kitchenette, and living area blends comfort, history, and charm. Just 20 minutes to Frederick & Harpers Ferry, it’s ideal for solo travelers, couples, or small families visiting this beautiful area. Blazing WiFi keeps you connected.

4.93 out of 5 average rating, 44 reviews

Top guest favourite

A cozy living area features a gray sectional sofa adorned with two white pillows. Natural light filters through the large windows, highlighting a round orange pouf and two side tables with lamps. Wooden beams are visible on the ceiling, enhancing the cottage’s rustic charm.

Home in Middletown

Mountain Church Cottage

Mountain Church Cottage offers a great stay in the hills of Middletown, Maryland. Activities nearby include access to the Appalachian Trail. The roads are a perfect challenge for the serious cyclist and runner, but it’s just a 15 minute drive to the flat terrain of the C&O Canal bike path. For kayakers, Potomac River access is in Harpers Ferry, West Virginia. It's just a short drive to Antietam National Battlefield. And for those who enjoy a glass, there are a number of wineries in the region.

4.96 out of 5 average rating, 156 reviews

Top guest favourite

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

Spacious Frederick Cty Retreat

Forget your worries in this spacious and serene space. 1 street over from Main St in Middletown. 15 minutes to the heart of Frederick. We are within walking distance of Main Cup, Tapias, Alekos, Abbraccio Gelato, 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.

5.0 out of 5 average rating, 36 reviews

Top guest favourite

The yellow farmhouse features a wrap-around porch and multiple gabled roofs, set against a gently sloping yard. Trees border the property, and a large rock is positioned in the foreground, contributing to the peaceful rural ambiance.

Farm stay in Knoxville

1813 circa Historical Farmhouse

Nestled atop a knoll with breathtaking views of rolling hills, pastures and beautiful South Mountain, our farm is your peaceful home away from home. Swing on the wrap around porch, or enjoy dinner on our 800 sq ft back patio. If adventure is more your thing, you will enjoy the walking trails, creeks and ponds. Guests will have exclusive access to the farmhouse and surrounding 2 acres. The remaining 27 acres is a working farm, with seasonal farm activity. Guests may explore the whole farm.

4.99 out of 5 average rating, 176 reviews

Top guest favourite

Farm stay in Middletown

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.

4.95 out of 5 average rating, 80 reviews

Superhost

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

"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.

4.92 out of 5 average rating, 306 reviews

Top guest favourite

A well-lit deck hosts a modern soaking tub, surrounded by forest views. Steps lead down from the deck, which is adorned with warm lighting that highlights the natural wood. The evening sky offers soft hues as the sun sets beyond the trees.

Home in Harpers Ferry

Gorgeous cabin on Blue Ridge

Atop the Blue Ridge close to Harper’s Ferry and Virginia wine country this airy retreat overlooks the idyllic Shenandoah. Our two-person soaking tub on a magnificent deck, huge firepit, gorgeous vintage interior, grand piano, and warm pine ceiling and floors, give you the perfect place to get away from city life for a bit. Full kitchen. Two bedrooms plus a big couch that could sleep someone else in a pinch, and a cozy little fireplace top it all off! Just steps to the Appalachian Trail.

4.97 out of 5 average rating, 136 reviews

Top guest favourite

Farm stay in Leesburg

The Forge on Sunnyside Farm

Sunnyside Farm offers a luxurious stay in a beautifully restored historic forge. You’ll be greeted by the farm’s delightful hosts, Jimmy and Dean, two friendly Potbelly pigs. Beautiful cows forage right outside your door. The Forge features exposed wooden beams, brick walls, and cozy furnishings. The interior is designed with plush bedding, a fully equipped kitchen, and spacious living reminiscent of yesteryear. Breweries, wineries and famous antique stores nearby offer entertainment.

5.0 out of 5 average rating, 149 reviews

Top guest favourite

A well-maintained pathway leads to a welcoming front porch, flanked by neat lawns and vibrant flowering bushes. Soft sunlight filters through the trees, casting delicate shadows on the concrete surface, while rolling hills can be seen in the background.

Home in Middletown

Beautiful historical town, 3 bedrooms, countryside

Beautiful home is on the 3.5 acres around peaceful farm area, with a barn and stunning views of the valley and mountains. You are able to see and hear the neighbor’s animals, see the rhythm of farm life, and enjoy being in nature. We hope you will find the house is supper comfy, welcoming. Great location not too far from Main St in Middletown with its restaurants & shopping. Minutes from the highway, yet still in the country. A little over 20 minutes drive to the Whitetail Ski Resort.

4.97 out of 5 average rating, 91 reviews

Guest favourite

A vibrant sunset paints the sky with shades of orange, pink, and purple, casting a peaceful glow over the distant valley. Silhouetted trees frame the scene, highlighting the natural beauty beyond the house.

Home in Frederick

Amazing view of the Middletown Valley

Comfortable and casual, this interior encourages group interaction and peaceful alone time. The view is one of the best on the "Boulevard", stretching all the way to Harper's Ferry. You can see all the major gaps where the battles took place during the South Mountain campaign in the Civil War. You are ten minutes from the bustling dining and shopping area of downtown Frederick and you can peacefully cook out on the deck while gazing across the valley when you return for the evening.

4.91 out of 5 average rating, 116 reviews

Guest favourite

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

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.

4.95 out of 5 average rating, 62 reviews