Holiday rentals in Middleburg

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Top-rated holiday rentals in Middleburg

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Guest favourite
A stunning sunset is displayed over a rural landscape, with warm orange and yellow hues spreading across the sky. Silhouettes of trees and rolling hills create a serene backdrop, while the softly illuminated horizon adds to the tranquil atmosphere.
Farm stay in Union Bridge
4.94 out of 5 average rating, 200 reviews

UB Paradise - Rustic, Relaxing, Amazing View

A unique rustic atmosphere, relaxing location with amazing view. Private entry, open floor plan basement is 1,300 square feet; 4 double beds, wrap around window seat, bar with kitchenette, bath/shower, and game area. We welcome those who are looking for a unique place to stay. We are close to Taneytown (Antrim 1844), Gettysburg, Frederick, Ski Liberty, Catoctin Mountain, Carroll County Wine Trail, Flood Zone. We do live upstairs, you are renting a walkin basement, and have use of outdoor spaces.

Top guest favourite
A historic stone farmhouse from 1861 is set on a well-maintained lawn, surrounded by green shrubbery and trees. The two-story structure features red shutters on the windows and a welcoming front porch that invites relaxation.
Home in Gettysburg
5 out of 5 average rating, 292 reviews

Civil War Farm House w/Heated (seasonal) Pool

Welcome to this historical Civil War Farm House. This stone home built in 1861 by Christian Shriver and was actively used as a field hospital during the war. Mrs Shriver prepared General Reynolds his breakfast on the first day of the battle (which he was killed). The Durboraw's moved here in the early 1890's and have remained here on the farm ever since. Please note, pool is open seasonally mid-May through mid- Sept. Please inquire to its opening/closing if booking around these times.

Top guest favourite
A scenic outdoor view showcases a wooden deck winding down to a lush landscape. Vibrant flowers and greenery adorn the space, while a hot tub is visible nearby. A beautiful sunset casts warm hues across the sky, offering panoramic views of the valley below.
Guest suite in Harpers Ferry
4.99 out of 5 average rating, 279 reviews

Luxury Mountain Getaway: Sunsets, Wines & Views.

Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the Sunset Rouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heavens to catch a falling star. Within 2 miles is Lake Shannondale with beach access provided by the Mountain Lake Club.

Top guest favourite
Place to stay in Shippensburg
5 out of 5 average rating, 450 reviews

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ

Escape to the charming 2BR 1Bath A-frame on a secluded wooded property just 10 mins away from Shippensburg, PA. Whether you're looking to savor nature‘s tranquility from the luxurious hot tub, share stories around the fire pit, or explore picturesque Cumberland Valley, this will be the ideal starting point for your adventures! *2 Comfortable BRs *Open Design Living *Full Kitchen *Smart TV *Backyard (Hot Tub, Sauna, Fire Pit, BBQ, Outdoor shower) *High-Speed Wi-Fi *Free Parking *EV charger

Top guest favourite
The historic stone house features a large front porch with a railing and several steps leading to the entrance. Its facade includes multiple windows framed by red shutters, with a modern addition visible on one side. Lush green grass surrounds the house, adding to the rural setting.
Farm stay in Mount Airy
4.98 out of 5 average rating, 115 reviews

Poole House at Friendship Farm

Welcome to Poole House at Friendship Farm! Escape to the country at this historic stone house built in the 1700s. With accommodations for eight guests it is perfect for a getaway with friends and family, wedding parties and work retreats. The house received a meticulous restoration that includes all mechanical systems and a modern addition with a gourmet kitchen and master bedroom. The property also includes a three car garage as well as a restored smoke house and log cabin.

Superhost
A cozy bedroom features a spacious bed complemented by a neutral-colored blanket. Wooden flooring and a rustic dresser add warmth, while an angled ceiling showcases natural wood panels. Soft light filters through the window, enhancing the tranquil atmosphere.
Flat in Gettysburg
4.87 out of 5 average rating, 100 reviews

Summer Kitchen

This renovated ‘summer kitchen’ is close to Gettysburg battle field and Gettysburg university. There are a set of fairly steep steps that lead to the bedroom, so please ensure that you are able to climb these (see pics). There is a small sitting room, bathroom and kitchenette on the first floor, and the bedroom is the only thing on the 2nd floor. There is plenty to do in historic Gettysburg, or if you like to ski or snowboard, Ski Liberty is only about 20 mins away!

Top guest favourite
A cozy living area features a yellow sectional sofa adorned with blue and patterned pillows. A glass coffee table with a dark wooden base sits in front. Two framed bird prints hang on the wall above the sofa, while a floor lamp and a decorative mirror enhance the space.
Flat in Union Bridge
5 out of 5 average rating, 214 reviews

Luxury, Charm and Privacy in Spacious Apartment

This light and airy, basement walkout apartment is located off the beaten path on a beautiful country acre. This airy space is filled with character and charm and is fully equipped. The apartment is perfect for couples, solo adventurers, and business travelers. Located 7 miles from McDaniel College and Westminster, 20 miles from Gettysburg, and 23 miles from Frederick, it's a great location for dining, exploring, shopping and enjoying all the college has to offer.

Guest favourite
A polycarbonate dome is nestled among trees, illuminated in soft green light. The spacious deck includes a seating area and a small table. A colorful sunset is visible in the background, casting a warm glow over the Appalachian landscape.
Dome in Shippensburg
4.91 out of 5 average rating, 147 reviews

Spectacular views, intimate dome

Come experience a truly one of a kind polycarbonate dome tucked away in the Appalachian mountains! Situated on the mountainside overlooking the scenic Cumberland valley. Complete privacy, stunning sunsets, and amazing amenities! The dome is climate controlled. The spacious deck is equipped with a meticulously maintained hot tub, and a blackstone griddle. This offers the unique opportunity to be immersed in nature, yet enjoy numerous amenities and comfort.

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, 628 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 modern cabin is nestled among trees, featuring a sleek design with large windows that allow light to emanate from within. The surrounding rocky terrain is softly illuminated by exterior lighting, creating a calm ambiance in the early evening fog.
Holiday home in Front Royal
4.99 out of 5 average rating, 410 reviews

Mountaintop Retreat with Wood Fired Hot Tub

Doah House is a private retreat perched on a bluff atop the Blue Ridge, with wide views over the Shenandoah Valley. A calm container for rest and observation, the pace softens, shaped by small rituals: lighting the fire, soaking in the wood-fired tub, making coffee by hand. Weather moves through the trees, changing the light, the air, the sound. Each day feels different. The forest shifts, and you might, too.

Top guest favourite
A spacious living area showcases high wooden beams and large windows allowing natural light. A cozy sofa is arranged with decorative cushions, while books line the walls. A dining table is positioned to one side, with a variety of plants adding a touch of greenery.
Farm stay in Taneytown
4.91 out of 5 average rating, 237 reviews

The Red Barn

The Red Barn is located in a very rural setting about 10 miles from Gettysburg. The Red Barn is approximately 1/2 mile off the main road and within a stone's throw of the Mason Dixon Line. If you are looking for a quiet space with not super internet this is the place. Plenty of books to read, miniature donkeys to watch playing with their border collie pal and on a clear night - see some awesome stars!

Guest favourite
A charming cabin with a wooden exterior is framed by a lush green lawn. A covered porch features two wooden benches, providing a welcoming entry. The structure is accentuated by a round window above the door, surrounded by open sky and trees in the background.
Cabin in Walkersville
4.92 out of 5 average rating, 106 reviews

Walkersville Cabin

The whole group will enjoy easy access to everything from this centrally located place. The cabin is located within minutes to the city of Frederick, Gettysburg and Cunningham falls state park. For an extra $50 a night we have a beautiful pool bar available. It is equipped with heat, a/c. 65 inch TV, bar stools, speaker and led lights everywhere.

Popular amenities for Middleburg holiday rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Carroll County
  5. Middleburg