There’s something special about walking into a home that holds stories from centuries past. The creak of old wood floors, original stone fireplaces, or the simple charm of period details carry a sense of time you just can’t replicate in a modern build. And the best part? You don’t have to admire them only from a distance. Many historic homes have been lovingly restored and opened up as vacation rentals, so you can experience history up close.
Whether it’s a colonial farmhouse, a Victorian gem, or a cottage that’s seen generations pass through its doors, these stays offer more than just a roof over your head. They give you a glimpse into the past while still providing the comforts you expect today.
Historic Stays Worth Booking
1. Large Historical Home for Groups, Walk to Downtown - Pensacola
This Pensacola treasure, built in 1904, is one of the city’s most architecturally significant Victorian homes. Step inside and you’re immediately greeted by soaring ceilings, hand-carved mantels on seven decorative fireplaces, and stained-glass windows that still glow with color more than a century later. The ornate wooden staircase is a centerpiece, reminding guests of a time when craftsmanship and elegance defined family homes. This lodging is a step back into Florida’s past.
Over the years, this home has worn many hats: from private residence to hotel, to bed-and-breakfast, and even an advertising agency. Today, it welcomes guests for special occasions, like weddings, military celebrations, and family gatherings, offering a sense of continuity with all who’ve passed through its doors before. The rooms are filled with antiques from different eras, adding layers of history to every corner, while wraparound porches and parlors create spaces to linger, talk, and reconnect.
Located in Pensacola’s North Hill Preservation District, just steps from Palafox Street, the house is perfectly placed for those who want both history and convenience. You can walk to markets, shops, and cafés, then return to a home that feels both grand and welcoming. Whether you’re hosting a group or simply looking to soak up the atmosphere of a bygone era, this is a living piece of history where guests are encouraged to add their own stories.
2. Kerlerec Kottage - Historic Treme Luxury - New Orleans
Built in 1866, this Treme home brings the spirit of old New Orleans to life. Its antique furnishings and historic bones tell the story of a city steeped in culture, yet thoughtful renovations mean guests enjoy the best of both worlds. Central air, instant hot water, and high-speed Wi-Fi keep things comfortable, while the character of the past remains very much intact.
Staying here means being just steps from history in motion. The French Quarter is a short stroll away, and even closer are Treme’s legendary jazz clubs, where the birthplace of jazz still hums every night. It’s the kind of place where you can spend the evening immersed in music and return home to a quiet courtyard or cozy antique-filled room that whispers of another century.
With secure parking and a private backyard, the home balances city energy with a peaceful retreat. It’s an authentic slice of New Orleans, allowing guests to soak up the neighborhood’s cultural richness while also enjoying a tranquil space of their own. For anyone drawn to history, music, and the magic of the Crescent City, this home offers a stay that’s convenient and deeply connected to its roots.
3. The Schoolhouse Cottage: Historical & Dog-friendly - Dahlonega
Tucked away in the hills of Dahlonega, the Schoolhouse Cottage lets you live inside a piece of 19th-century history. Once a working schoolhouse, it still holds its original floors, ceilings, and windows, giving the space a tangible connection to the past. The restoration kept those details intact while layering in comfort—think soft beds, a well-stocked kitchen, and antiques chosen with care.
The vibe here is slower, warmer. You might find yourself sitting on the porch with a soda in hand, or curling up inside, surrounded by pieces that remind you this home has seen generations pass through. And while the historic charm is front and center, it’s never at the expense of convenience. The cottage is pet-friendly with no extra fee, making it easy to bring your four-legged companion along for the trip.
It’s the kind of stay that works for everyone—couples looking for a romantic hideaway, solo travelers seeking quiet, or families wanting a touch of nostalgia. Blending history with hospitality, the Schoolhouse Cottage is an experience that connects you to the past while offering the comforts of the present.
4. Historic Home in Ybor - Steps Away From 7th Ave - Tampa
Casa Alma, built in 1927, is a slice of Tampa’s history that’s been given new life without losing its charm. Just blocks from Ybor City’s famous 7th Avenue, this home pairs original features like tall ceilings, wood floors, and a breezy front porch swing with updated touches that make it practical for today’s travelers. It’s the kind of place where you can step outside for nightlife and restaurants, then return to a quiet, cozy space that feels rooted in another era.
Inside, the house balances old and new. Natural light fills the rooms, highlighting details that nod to its history, while modern appliances and stylish furnishings keep it comfortable. Bedrooms are thoughtfully arranged, with two queen rooms (one ensuite with a desk) and a twin room, making it flexible for groups or families. The kitchen and dining nook invite casual meals at home, but the true magic often happens in the backyard, where a fire table under the stars sets the scene for memorable evenings.
What makes Casa Alma special is its mix of character and location. You’re in the heart of historic Ybor, surrounded by Cuban coffee, neon lights, and music spilling out of bars, yet the home itself feels like a retreat. Whether you’re here for Tampa’s energy or the simple joy of sitting on a porch swing at sunset, this historic gem offers both.
5. Historic Farm - Relax, Hike, & Fish - Pet Friendly - Rockbridge Baths
The Farm at Jump View, built in 1870, is a farmhouse that feels like stepping into history while still giving you modern comfort. Surrounded by pastureland and nestled beneath Jump Mountain, it captures the kind of peace that makes you forget the bustle of everyday life. From the moment you cross the little bridge over Walker’s Creek to reach the property, you’re welcomed into a retreat where time slows down and the beauty of the Virginia countryside takes center stage.
Inside, the farmhouse blends rustic décor with functionality. Original charm is everywhere—from the wood finishes to the cozy living areas—yet it’s fully equipped for travelers. With four bedrooms, three baths, and plenty of gathering space, it works just as well for families as it does for groups of friends. Guests can cook together in the spacious kitchen, relax on the screened-in porch, or stay active on the property’s tennis and basketball courts. It’s history lived in, not just looked at.
What makes this home special, though, is the experiences it encourages outdoors. Days can start with coffee while cows graze nearby and end beside the firepit, watching the sunset fade into starlight over Jump Mountain. Fall guests will especially love the foliage hikes at Goshen Pass or the chance to sip wine at nearby vineyards before returning to the farmhouse for an evening by the fire.
6. 1930s Queen Anne Historic Downtown Retreat - Medford
This 1936 Queen Anne home brings together history, elegance, and comfort, all within walking distance of a lively downtown full of shops, parks, and restaurants. From the outside, its classic architectural style nods to nearly a century of character, while inside, careful renovations have made it a welcoming retreat for families or groups.
The first floor sets the tone with a spacious master suite featuring a spa-like bathroom—heated floors, rain shower, and even a cast-iron tub that feels like a true luxury. The kitchen is set up for entertaining with two full-size fridges, a gas stove, and a wine bar. Between the large dining table, wood-burning fireplace in the living room, and fenced backyard with a grill and play structure, the home is designed to bring people together.
Upstairs, three more bedrooms offer flexible sleeping arrangements, making this property well-suited for groups of up to eight. Whether you’re gathered for a holiday, planning a weekend escape, or simply looking to explore a historic town on foot, this Queen Anne provides a blend of nostalgia and practicality. It’s a place where you can enjoy evenings by the fire and mornings with coffee in a sunlit dining room—proof that history and modern living can blend beautifully.
Your Next Historic Stay Awaits
At the end of the day, there’s something special about choosing a stay that tells a story. These historic homes aren’t just vacation rentals; they are living pieces of history. Houfy makes it easy to find and book these one-of-a-kind homes directly from hosts—no hidden fees, just a few clicks to secure your stay. If you’re ready to step into history and enjoy a getaway that feels both timeless and personal, browse Houfy today and start planning your next trip.
