Vacation rentals in Middleburg

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Top-rated vacation rentals in Middleburg

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Guest favorite

Cabin in Myersville

4.97 out of 5 average rating, 251 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Amazing place to unwind, de-stress & get away. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting.

Sep 4 – 11

ﺩ.ﺇ416 per night

Superhost

Farm stay in Union Bridge

4.93 out of 5 average rating, 176 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.

Aug 17 – 24

ﺩ.ﺇ681 per night

Guest favorite

Guest suite in Littlestown

4.88 out of 5 average rating, 216 reviews

Gettysburg Mini Farm

A quiet mini farm just outside historic Gettysburg. Private entrance. Living area, full kitchen stocked with condiments and breakfast items. One bedroom with queen bed and twin daybed with trundle. We currently have chickens, an apiary and alpacas. We sometimes have cows. TV works with dvd's. we have some feel free to bring your own. SLOW internet, but the best we can get here. Some phones do not work very well out here. Only 15 minutes from downtown Gettysburg but we are far from services.

Jun 20 – 27

ﺩ.ﺇ372 per night

Guest favorite

Loft in Walkersville

5.0 out of 5 average rating, 128 reviews

Daysville Inn- Boho Farmhouse Apt

This farmhouse apartment is perfect for your next visit to the Walkersville/Frederick MD area! Peacefully private from the hosts’ home, and conveniently located just 2 miles from the popular Walkers Overlook Wedding Venue, and 7 miles from the fun downtown Frederick! With many popular breweries/wineries surrounding it, it’s your perfect weekend getaway! It even comes with 4 friendly goats our guests are welcome to pet! No hotels are closer! We hope you book your stay today at Daysville Inn!

Sep 25 – Oct 2

ﺩ.ﺇ376 per night

Guest favorite

Cabin in New Oxford

4.9 out of 5 average rating, 598 reviews

Conewago Cabin - Near Gettysburg!

Rustic, cozy one-room apartment down a long lane on the Conewago river. The apartment is attached to the house but has its own entrance without going through the main house. Private bathroom and shower included. PLEASE NOTE: There are several steps in the cabin going down into the kitchen, up into the living room, and down into the bedroom nook. The floor of the bathroom is not completely even. This cabin may not be suitable for senior citizens or those who have problems with mobility.

Jan 23 – 30

ﺩ.ﺇ252 per night

Guest favorite

Guesthouse in Myersville

4.93 out of 5 average rating, 190 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.

Jun 21 – 28

ﺩ.ﺇ364 per night

Guest favorite

Home in Myersville

4.97 out of 5 average rating, 145 reviews

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!

Oct 5 – 12

ﺩ.ﺇ615 per night

Guest favorite

Guest suite in Fairfield

4.88 out of 5 average rating, 129 reviews

Gettysburg-Ski-Golf-ATHikes - RoseSniffers Loft

Calling all RoseSniffers!! Stop and smell the roses in this newly constructed, stylish studio with private entrance. Although you will wake up to a bird's eye view of mountains, farms, and a golfcourse, you will be minutes away from four-season adventures: Skiing, Antiquing, Vineyards, History, Gettysburg Military Park, 5-Star Golfing, Performing Arts, and Dining are all minutes away! We've thought of all your comforts of home and designed this place with your peace in mind!

Oct 9 – 16

ﺩ.ﺇ353 per night

Guest favorite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 641 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota guesthouse is the perfect get away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Jan 17 – 24

ﺩ.ﺇ339 per night

Guest favorite

Apartment in Union Bridge

4.99 out of 5 average rating, 197 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.

Sep 14 – 21

ﺩ.ﺇ353 per night

Guest favorite

Home in Blue Ridge Summit

5.0 out of 5 average rating, 448 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.

Sep 6 – 13

ﺩ.ﺇ496 per night

Guest favorite

Farm stay in Taneytown

4.9 out of 5 average rating, 187 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!

Aug 7 – 14

ﺩ.ﺇ580 per night