Some people love carving pumpkins and passing out candy. Others want a little more adventure out of the Halloween season. If you’re the second type, booking one of the many Halloween vacation rentals out there might be your thing.
These aren’t just regular vacation homes. We’re talking historic homes with ghostly tales, cabins in the woods with fire pits, and family-sized houses where you can swap ghost stories. Thankfully, we did the digging, so you don’t have to. Here are the best Halloween vacation rentals you can book right now on Houfy.
Halloween Vacation Homes You Can Book for 2025
1. 2817 Storey Lake - Kissimmee
This villa in Storey Lake Resort feels like it was built for Halloween escapes. The theming alone sets the mood: Harry Potter’s four-poster bed with floating candles, a glowing Star Wars bunk room with lightsabers, and a castle-style Princess suite with its own slide. Add in a private cinema room and games arcade upstairs, and you’ve got all the makings of a Halloween getaway where kids and adults can lean into the spooky season without ever leaving the house.
Outside, the private pool and hot tub turn into gathering spots after the sun goes down. Imagine swapping ghost stories by the water, speakers playing in the background, and maybe sneaking into the Harry Potter room for extra atmosphere. For families, it’s also a chance to spend Halloween together in a different way—dressing up, cooking a meal in the large kitchen, or watching a scary movie marathon in the cinema.
Since Orlando is minutes away, you could add theme park haunts to the mix, then come home to your own private “haunted house.” Leaning into Halloween never felt easier.
2. Greatmen Cottage Vacation Rental Home - New Orleans
Greatmen Cottage in New Orleans is the kind of place where history sets the stage for a Halloween vacation. Built in 1838, this Creole cottage has the classic architecture—high ceilings, tall windows, old brickwork—that instantly gives off a spooky-season vibe. Staying here during October means you’re surrounded by the city’s ghostly tales, jazz-filled nights, and streets where the Halloween spirit is woven into everyday life. It’s not hard to imagine candlelight dinners in the dining room followed by quiet walks through the historic Bywater district.
Inside, the house features a copper-countered kitchen, a sunroom with brick floors, and spacious living areas that give families and groups room to gather. The double bathroom setup upstairs is practical, while the terrace and gardens outside are perfect for slower evenings. For Halloween, it’s less about costumes and more about atmosphere—sharing ghost stories in a house that’s stood through centuries, then heading out to enjoy the city’s festive atmosphere.
Location is everything. Just minutes from the French Quarter, guests can explore haunted tours, jazz clubs, and late-night food spots that make New Orleans famous in the Halloween season. And back at the cottage, you’ve got privacy, space, and a home base that feels both historic and welcoming. Whether it’s sipping something warm on the terrace or walking through Crescent Park at dusk, this rental gives you an authentic Halloween getaway wrapped in New Orleans’ unmistakable charm.
3. Château Des Deux Rives - Dinard
Château des Deux Rives feels like it was made for a Halloween getaway. Built in 1878, this three-story residence has the kind of history and character that make you pause. The high ceilings, sea views, and quiet halls give it a slightly mysterious air, especially when you think about the generations who’ve lived there before. Staying here in late October means you’re not just booking a place near the beach—you’re stepping into a piece of the past that naturally fits the Halloween season.
Inside, the apartment combines modern comfort with old-world charm. Spacious rooms, cozy furnishings, and a bright kitchen make it practical for families or small groups, while the panoramic view of the sea adds a dramatic backdrop to your stay. Imagine sharing ghost stories in the lounge as the wind picks up outside, or taking a moonlit walk on the sandy beach just steps away.
And when you’re ready to explore, the location adds even more to the experience. You’re close to Saint-Malo’s medieval walls, Dinan’s historic streets, and even Mont Saint-Michel, which has its own legendary aura. In the evenings, you can return to your quiet retreat, perhaps with a glass of wine in hand, while the sea reflects the fading light.
4. Large Historical Home for Groups, Walk to Downtown - Pensacola
This Victorian home in downtown Pensacola feels tailor-made for a Halloween getaway. Built in 1904 and packed with historic details like stained glass windows, grand staircases, and seven original fireplaces, it has the kind of atmosphere that sparks curiosity. Walking through its halls, you can almost imagine the generations of families, guests, and even businesses that passed through. For Halloween 2025, it’s easy to see this house as more than a rental.
The size alone makes it perfect for family gatherings or groups looking for an immersive experience. With six bedrooms, six bathrooms, a parlor, library, and even a movie-themed room, there’s space for everyone to spread out while still coming together for shared meals or evenings on the wraparound porches. You can sit in the library swapping ghost stories, or enjoy the ornate fireplaces as a backdrop for a relaxed night in. The antique furnishings add to the spooky season feel.
Step outside, and you’re right in the heart of historic Pensacola, just a short walk from Palafox Street with its shops, restaurants, and markets. Exploring the neighborhood during the Halloween season could easily add to the festive atmosphere, while returning to this century-old home each night keeps the eerie charm going. For travelers wanting a vacation rental that blends history, architecture, and the perfect setting for a Halloween getaway, this Pensacola mansion is hard to beat.
5. The Cabin at Morris Orchard - Monroe
The Cabin at Morris Orchard has the kind of atmosphere that fits right into the Halloween season. Built in the early 1800s and carefully rebuilt to preserve its history, it carries the quiet weight of two centuries of life. Surrounded by apple orchards, hayfields, and pastures, it’s a secluded escape where the only sounds are the rustle of trees or cattle in the distance. For Halloween 2025, staying here feels less like booking a vacation rental and more like stepping into a piece of American history.
Inside, the one-bedroom cabin is cozy and simple, with wood from the original build woven into the design—ash stairs, chestnut doors, walnut shelves. Sitting by the firepit on a cool October night, you could imagine sharing ghost stories as the pond reflects the moonlight. The mix of rustic details with modern comforts like Wi-Fi and a full kitchen makes it easy to settle in while still soaking up the historic atmosphere. It’s a place where the past lingers in the walls, adding just enough intrigue for a Halloween getaway.
The setting itself makes the experience complete. From the porch, you look out over High Peak Mountain and the family farm’s apple orchards, which adds a festive autumn feel. Walking the grounds, you’re reminded how much history has unfolded here, and how many stories the cabin must hold. While it’s peaceful and calm, it has just the right touch of mystery to make your Halloween vacation feel special and steeped in tradition.
6. Castle St. Croix - Christiansted
Castle St. Croix is the only true castle in the Caribbean, which already makes it feel like the perfect backdrop for Halloween. Perched high on a hill, the property overlooks the sea with 360-degree views that feel both grand and a little mysterious. With its stone walls, hand-painted murals, and lavish interiors, the space carries an old-world elegance that makes you imagine ghostly tales from centuries past, even though the castle itself was built in the 1980s.
Inside, there’s enough room for up to 10 guests, making it a fit for family gatherings or friends looking to spend Halloween in a place that feels dramatic and unforgettable. The dining room, with its painted ceiling, looks like the kind of place where you’d light candles and linger late into the night over delicious food. Outside, the custom pool grotto and lush gardens are beautiful in the day but can take on an atmospheric, almost otherworldly vibe once the sun sets.
While it’s undeniably luxurious, Castle St. Croix also lends itself to a more imaginative experience. The size, the hilltop perch, the sweeping sea views—it all feels like the setting of a story. Instead of haunted halls, you get a regal retreat where the festive atmosphere comes from the castle itself and its surroundings. For Halloween 2025, staying here would mean swapping trick-or-treating for a private escape in the Caribbean.
Finding the Right Halloween Getaway
Halloween doesn’t have to be about crowded events or packed streets. Sometimes the best way to celebrate Halloween is by stepping into a space that feels a little mysterious, historic, or even secluded. Once you find the rental that clicks, booking directly on Houfy makes the whole process easier. No extra fees, no middleman, just a straightforward way to spend Halloween in a place that feels perfect for the season.
