Middleburg Cottages

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Cottages in Middleburg

Apple Blossom Cottage! HT Extra Cost

Orrtanna PA

Located in Orrtanna, this cottage is in a rural location, within a 10-minute drive of Adams County Winery and Gettysburg National Military Park.

Hot Tub

Kitchen

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Frederick MD

$250 nightly

$265 total

Jan 7 - Jan 8, 2026

Total with taxes and fees

With a stay at this cottage in Frederick, you'll be within a 5-minute walk of Baker Park and Frederick Memorial Hospital.

Kitchen

Pet friendly

Creekside Cabin at Gettysburg

Gettysburg PA

Located in Gettysburg, this cottage is in a rural location, within a 10-minute drive of Seminary Ridge Museum and Gettysburg College.

Kitchen

Washer

Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

Thurmont MD

With a stay at this cottage in Thurmont, you'll be within a 15-minute drive of Gettysburg National Military Park and Mount St. Mary's University.

Kitchen

Washer

Cozy Cottage near Skiing, Gettysburg, and Hiking

Waynesboro PA

With a stay at this cottage in Waynesboro, you'll be within a 15-minute drive of Liberty Mountain Ski Resort and Monterey Pass Battlefield Museum.

Air conditioning

Parking available

Cozy Fairfield Escape Near Historic Sites

Fairfield PA

With a stay at this cottage in Fairfield, you'll be within a 5-minute drive of Liberty Mountain Ski Resort and Mountain View Golf Club.

Kitchen

Washer

Farmhouse on River, 12 Miles to Liberty Mountain

Taneytown MD

Located in Taneytown, this cottage is within a 15-minute drive of Taneytown Memorial Park and Emmitsburg Historic District.

Kitchen

Parking included

Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!

Smithsburg MD

With a stay at this cottage in Smithsburg, you'll be a 1-minute walk from Hagerstown Edgemont Reservoir and 6 minutes by foot from Hagerstown Watershed.

Washer

Dryer

Equestrian Escape! Quiet Farm Stay Near Gettysburg

Union Bridge MD

Located in Union Bridge, this cottage is within a 15-minute drive of Loew Vineyards and Elk Run Vineyards.

Kitchen

Pet friendly

Historical Thurmont Escape w/ Furnished Deck!

Thurmont MD

With a stay at this cottage in Thurmont, you'll be steps from Cunningham Falls State Park and a 2-minute drive from Catoctin Wildlife Preserve and Zoo.

Kitchen

Parking included

Upscale Country Home w/ Fire Pit in Taneytown!

4107 Ruggles Rd Taneytown MD

Located in Taneytown, this cottage is within a 10-minute drive of Taneytown Memorial Park and Roberts Mill Park.

Kitchen

Washer

Peaceful Home w/ Patio < 2 Mi to Nat'l Park!

Thurmont MD

With a stay at this cottage in Thurmont, you'll be a 3-minute walk from Thurmont Park and 9 minutes by foot from Thurmont Memorial Park.

Kitchen

Washer

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.