Holiday rentals in Hillsdale

Marie's Place, a cozy house right off the square!

Two bedroom, one bath home with two large living areas, kitchen, laundry room and large front porch. Marie's place is within close walking distance to town square where you can enjoy the fun little shops, antique shopping or even events that take place (craft shows, smoking competitions, car shows, concerts etc.). We are located within walking distance to the Miami County Wine Trolley pick-up spot as well. You can also enjoy golf, fishing, and many other activities within close driving distance.

Spacious Country Apartment with Modern Amenities

Welcome to Louisburg! Spacious, private entry, 1000 sq. ft. apartment above detached garage within minutes of wineries, antiques & Cider Mill. Set on 15 acres, and 2 miles down a gravel road, you are out of the city and seeing stars, with an amazing 2nd story view. Sleeps up to 6 with separate bedroom with queen bed and low ceiling (62” great for kids!) loft with 2 twins & a double. All wrapped in unique finishes including an amazing shower! Located only 45 minutes from downtown Kansas City!

Modern 3 Bedroom Home, Sleeps 7, F WiFi + Parking

Welcome to Ariel Stays Enjoy a peaceful and stylish home designed for comfort, relaxation, and productivity. Perfect for professionals, couples, or anyone looking for a quiet and clean place to unwind. What you’ll love: • Cozy and comfortable beds with fresh linens • Dedicated workspace with desk and chair • Fast Wi-Fi for work • Fully equipped kitchen • Free parking on premises Located in a safe and quiet area of Overland Park, close to shopping, restaurants, and everything you need.

Luxe lake cabin 1hr to Kansas City w pool+hot tub

Welcome to the Butterfly Pods, by PodHopping, where eco-conscious living meets modern comfort in our Passivhaus-standard cabins. We generate our own power, manage our own water, and work with nature’s rhythms. It’s a chance to slow down and reconnect with the earth, and your loved ones. Lounge in a hammock, swim, soak in the hot tub, kayak on the lake, and gather around the fire. Come experience off-grid living and leave refreshed, with a greater appreciation for the resources we all share.

The Loft at Sozo

Historic Luxury on Main Street Welcome to The Loft at Sozo, a stunning retreat nestled above Main Street in the heart of historic Spring Hill, Kansas. Located in a beautiful 1886 building, this styled space blends modern luxury with timeless charm—perfect for solo travelers, or couples, seeking a peaceful getaway. Exposed brick walls, and original hardwood floors set the scene, while a spa-style soaking tub, full kitchen, and cozy layout offer everything you need to relax and recharge.

The Cottage: Luxurious Getaway!

Escape to luxury at this private cottage with indoor 17-ft swim/spa, sauna, and steam shower. Sleeps up to 10 with beds, air mattresses, and convertible furniture. Enjoy a fenced patio, fire pit, robes, slippers, face masks, Nespresso, and more. Perfect for a romantic getaway, group stay, or small event (max 15). Includes kitchen, lounge areas, smart tech, and walkable access to downtown Eudora. No pets. Quiet hours 10p–8a. Swim at your own risk. Property is not child-proof.

Meadow Brooke Lane

Nested on 3 beautiful acres of fenced land. 4 bedrooms (3 with ensuite), fully equipped kitchen, projector, fire, bbq, plus more! This property is located near multiple event spaces making it ideal for small gatherings or enjoying the countryside. Kids and pets alike with love the vast outdoor space to roam and play. There is a charming train that runs the backside of the property making for a unique and fun backdrop. A fantastic dog friendly brewery is within walking distance.

Water & Light Yurt

Enjoy the serenity of nature when you stay in this traditional Mongolian Yurt nestled into our 6+ acre forest oasis in Kansas. Access to a creek, small lake (kayaks and canoe available), and forest trails, with lots of varieties of plants and wildlife. You will most likely see some of our friendly cats roaming around, too. Hillsdale Lake is right up the road with miles of horse/bike/walking trails and boats to rent. A beautiful experience in all four seasons! 🌱🌺🍂❄️

Cozy Historic Schoolhouse w/ Hot Tub + Views

✨Historic Charm Meets Modern Comfort on the Kansas Prairie✨ Vickers Schoolhouse at Crimson Ridge Flower Farm ★★★★★ “Truly a treasure! So cozy and quaint!” Looking for a peaceful countryside escape that feels a world away—but is still close to everything? Whether you’re planning a romantic getaway or a girls’ weekend full of laughter and relaxation, this beautifully restored 130+ year-old schoolhouse offers the perfect mix of nostalgia, charm, and comfort.

Clean, Spacious, Fully Renovated Townhouse Retreat

Charming and inviting townhouse located in the heart of a quaint small town just outside Kansas City. Ideal for a weekend getaway, business trip, staycation, or cozy home base while exploring everything the area has to offer. Enjoy a fully renovated space featuring a stylish blend of modern décor and comforting touches of home. Just a short stroll away, you'll find a local coffee shop, ice cream parlor, and unique vintage stores to explore and enjoy.

Brickhaven Inn: indoor pool, sports court, arcade!

Brickhaven Inn is a stunning renovated stone church turned luxury retreat. Sleeps 18+ with spacious living, dining for 18, full kitchen, and four unique bedrooms. Enjoy an indoor heated pool, indoor putting green, sports court for basketball and pickleball, arcade games, shuffleboard, pool table, massage chairs, and outdoor mini golf. Plenty of space and unforgettable amenities. A portion of your stay is donated to Eudora Community Food Bank!

Fall for Wade Ranch. Kansas Farm & Lake Stay.

Stay at a registered Kansas Agritourism Ranch. Leave the hustle and bustle of city life and experience what Wade Ranch has to offer! Stay in our historic 1869 Kansas farmhouse where rugged ranch life meets the serene beauty of Hillsdale Lake. Quiet and secluded, working ranch, private deer/game hunts, less than 30 min from Olathe, Kansas. Hunt, trail ride, boat, or fish. Adjacent to 10,000 acres of Hillsdale Wildlife and State Park.