Holiday rentals in Middleburg

The Roundtop Chalet (romantic couples retreat)

Indulge in a getaway to our charming cabin, the perfect retreat for all your special celebrations - be it anniversaries, birthdays, or simply a much-needed escape from routine. Perfectly designed for romantic getaways, this cabin seamlessly blends rustic charm with modern comforts. Savour the warmth of a cozy fireplace, unwinding in a hot tub,and indulge with unlimited lattes, crafted by our Breville Touch Espresso Machine. Embrace serenity at its finest and make memories that will last forever

Private Woodland Retreat | Near Downtown Frederick

Escape to a beautiful one-bedroom retreat. The guesthouse has a queen bed, kitchenette, luxurious bathroom with two shower heads, including a rain head, and a queen pull-out sofa bed. Nestled in the woods with a covered porch for morning coffee, yet a short drive to downtown Frederick, Civil War sites, Frederick Watershed with hiking and cycling trails, Mount St. Mary’s University, Cunningham Falls, and Catoctin. Free WiFi, and Smart Roku TV’s. Parking for 2 cars is included. Dogs are welcome.

Keymar Guest House

Escape to the country and enjoy the relaxation of scenic laid-back living. Our guest house is a private retreat attached to the main house on our 15 acre farmette. While the main house is over 100 years old, the guest house was added as an in-law suite in 2005. Enjoy the fresh indoor area, as well as the scenic outdoors with views of mountains, farms and open spaces. Centrally located to Frederick, Gettysburg and Westminster (30 minute drive) and Baltimore and Washington (60 minute drive).

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

The Great Escape Lodge ~ Exquisite Mountain Views

The Great Escape Lodge is a soaring A-frame offering luxury accommodations. Owner designed and custom built in 2022, this luxury getaway is nestled in the stunning Catoctin Mountains with views parallel to those seen on Paramount's hit series Yellowstone. This exquisite residence offers outstanding interior and exterior custom touches and amenities. From the open concept great room to the massive deck with rockers and hot tub, there are endless opportunities to enjoy the scenic views.

Keymar Cottage

Stay in this stone rancher in beautiful rural Frederick County half an hour from historic Gettysburg and Frederick. The property is surrounded by fields on three sides with a great view of the mountains (unless the corn is too tall). Watch the sunrise from the front porch and sit on the back patio to watch the sunset. There is a two-car garage and a macadam driveway for parking. The six-tenths acre property includes a nice grassy lawn, trees and shrubbery and a picnic table on the patio.

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!

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.

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.

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.

Stoney Spring Overlook

This beautiful mountain home offers breathtaking views of the surrounding Catoctin Mountains. The area is rich with outdoor adventures and attractions. Though it feels like a peaceful retreat tucked away in the mountains, it’s only 30 minutes from Frederick, MD, historic Gettysburg, PA, and about an hour from the Washington, D.C. area. Whether you’re seeking a quiet escape or hoping to explore more of the Frederick County.

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.