Vacation rentals in Jefferson

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Top-rated vacation rentals in Jefferson

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Top 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.

4.98 out of 5 average rating, 42 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.

4.95 out of 5 average rating, 155 reviews

Top guest favourite

Home in Adamstown

Wizard's Forbidden Hut | 2 Escape rooms | Sleep15+

NEW ADDITION - 3 Broomsticks Pub- Wizards and Humans are invited to experience the magic of Wizard's Forbidden Hut Escape - A magical hut located in a forbidden forest with an escape room twist. Immerse yourself in 2 thrilling themed escape rooms, daring Scavenger Hut or find and keep the hidden Owls. Perfect for family reunions, bachelorette/ bachelor parties. Weddings/ Large Events - additional cost. Follow us on Insta/Fb for videos. Rent the Wizard Escape Castle next door for larger parties.

5.0 out of 5 average rating, 70 reviews

Guest favourite

The guesthouse exterior presents a gray facade with a welcoming porch. Lush greenery, including manicured bushes and large trees, frames the entrance. A paved walkway leads to the door, surrounded by planters. The house stands under a clear blue sky, providing a serene setting.

Guesthouse in Middletown

Indulge, Fresh Flowers, Frederick County Haven

2 bedroom, full kitchen and laundry, 1 level guesthouse beside detached garage (separate from main house). The front has a rose garden, birdbath and your own patio. An apple tree is beside the guesthouse. A farm is to the back. Asian cafe, Subway, Dempsey's Grill, Amvets, Main Cup bar and restaurant, Tapia's and 3 ice cream parlors are all a short walk away. More restaurants and grocery store are less than a mile. Farmer's market in season on Thursdays. Fresh flowers and coffee are provided.

4.93 out of 5 average rating, 334 reviews

Guest favourite

A two-story house features a combination of green and beige siding, with prominent large windows allowing ample natural light. A well-tended garden with colorful flowers borders the entryway, enhancing the home's curb appeal. A garage door is visible on the left side.

Home in Frederick

More Luxury = Gym + Entertainment + Best Location

High End Architecturally unique house for the area with large vault ceilings. Enjoy the walk-out deck for a barbecue with outside dinning or the personal gym formally owned by a female Olympic weightlifter. The house is located on a quiet court with direct access to all major highways, 270, 15, 340 and 70. The location is one of the nicest most convenient spots in Frederick, one block away and you can enjoy the Golden Mile of restaurants and shopping, yet the subdivision is quiet & peaceful.

4.94 out of 5 average rating, 213 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, 78 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, 304 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, 144 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, 61 reviews

Top guest favourite

The entrance to The Crooked Cottage is framed by wooden planks and surrounded by greenery. Two windows offer glimpses into the inviting interior, while a gravel pathway leads up to the door, playfully adorned with a sign featuring the name of the cottage.

Home in Myersville

The Crooked Cottage: a Cozy, Curated Escape

You will instantly relax in this stylish, pet-friendly home only 8 mins from I-70, exit 42. Under a canopy of trees find a beautifully landscaped yard with decks and two fire pit areas. Enjoy the well-apportioned kitchen with organic, fair trade coffee. Relax with 2 Roku TVs, games and puzzles, bathe with soaking salts and Turkish towels. For outdoor enthusiasts, pitch your tents. Sit by the wood-stove in the winter, or lay in a hammock when it’s warm. Welcome to The Crooked Cottage!

4.98 out of 5 average rating, 316 reviews