Holiday houses in Mount Airy

The Caretaker's Cottage-Historic Roundabout Hills

The Caretaker's Cottage was built in the 1770s by Ruben Merriwether, and sits near the manor house where he and his ancestors lived at Roundabout Hills. An exceptional space with a fabulous full kitchen perfect for those who like to cook, it is truly a one of a kind place to stay. The house, where John and Fiona live, and the cottage are secluded and private, but close to all of the art, culture, restaurants and dining in the nearby towns of Frederick, Columbia, Baltimore, and Washington, DC.

The Everyday Farm Getaway

Unwind at this welcoming oasis surrounded by nature. This one bedroom 2nd floor apartment has views of the sunrise from the porch and the sunset from the bedroom. The cozy private space overlooks the property where deer, fox, and other wildlife roam and the host’s chickens, goats, cats, and dogs live. Creature comforts include a keurig, king bed, couch, kitchen table, WiFi, TV, and a deck. No parties, no gatherings of more than 2 people. NOTE: There are 2 flights of outdoor steps to enter.

Cozy West Virginia Treehouse

Thanks for checking out our treehouse! It’s 4 minutes from downtown Shepherdstown and 15 minutes from downtown Harpers Ferry. We are excited to share it with other fun-loving folks! The treehouse has heat and AC, a tiny kitchen with a mini fridge, stove top, toaster oven, gravity-fed sink and kitchenware. There’s a bathhouse built on the back of the host’s home with a conventional toilet and shower. There’s also an outhouse with a light and essentials. We provide wood for the fire pit also.

Beautiful Mount Airy Home -Wine Country, Views!

100% FULLY RENOVATED, 4 BEDROOM HOME & BEAUTIFUL VIEWS! Soak in the views from the spacious 2nd story deck, dining area & bedrooms. Enjoy the floor-to-ceiling stone fireplace, chef's kitchen & tile baths. Lots of light, hardwoods throughout! Smart TV's, wifi & cable. 4-minute walk to Historic Downtown Mt. Airy & 5-minute drive to restaurants & shops. Only 10 minutes to top local wineries! 35 minutes to Baltimore's Inner Harbor, outlets & Ellicott City! Come enjoy! You'll be glad you did!

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!

Gillis Carriage House 1 BR entire place pond view

Take a break and unwind at this peaceful oasis. This charming guest cottage is tucked away from the hustle and bustle, offering a quiet retreat to relax and recharge. Yet it's conveniently located less than 10 minutes from shopping, restaurants, and a major highway. Enjoy a cozy interior, peaceful surroundings, and easy access to everything you need. Whether you're here for a weekend getaway or an extended stay, this tranquil spot is the perfect place to slow down and feel at home.

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.

Sunsets from a Haven on a Hill

Come rest & relax in the high hill country of Mount Airy, MD. Find an oasis of beautiful views, rolling hills, open skies, and pastureland. This three-story farmhouse sits on one of the highest points in Mount Airy, MD with views of both the sunrise and the sunset. With an open kitchen plan, large family room, and beds to sleep 9, it’s a perfect place to gather family together for the holidays. Unwind, unplug, and connect with your loved ones in this beautiful farm setting.

The Gathering Place | Luxury Sauna Retreat

A peaceful Mount Airy retreat with an infrared sauna, cozy fireplace, 1 GB Wi-Fi, and plenty of space for families, wedding guests, winery weekends, and quiet midweek getaways near Frederick. Enjoy nature views, deer and bird sightings, workspace, game room, stocked kitchen, comfy beds, and inviting gathering spaces. Quiet cul-de-sac—less than 10 minutes to groceries, restaurants, Walmart, and downtown Mount Airy, with easy access to Frederick, DC, Baltimore, and Gettysburg.

Century Revival

Welcome to your perfect Mt. Airy getaway, where small-town charm meets comfort and convenience. Located in the heart of town and just minutes from I-70, this beautifully renovated 1910 home makes it easy to explore or unwind. Whether you’re here for a weekend escape, visiting family, or passing through, you’ll love the blend of historic character and modern updates. Enjoy your morning coffee on the wraparound porch or relax after a day out in this peaceful, inviting space.

Spacious Carriage Home Suite in Frederick MD

NEAR HISTORIC DOWNTOWN FREDERICK - Super Spacious 2nd Floor Guest Home Suite located on 5 Acres with an amazing view! Freshly painted and newly furnished with fresh appliances. Long Driveway entrance with plenty of parking available. Only 46 miles from Baltimore and 50 miles away from D.C. Downtown Frederick is only a couple of minutes away so you can enjoy shopping, restaurants, and experience everything Frederick has to offer!

Garden Cottage

Located in a beautiful and peaceful part of Maryland our Garden Cottage offers a cute and cozy getaway. A perfect escape from the city, our cottage is nestled among some of Maryland's best farmers markets, breweries, wineries, and outdoor experiences while still being conveniently located near several small towns and Frederick, MD. If you’re looking for a longer stay but our calendar looks booked please reach out to us!