Holiday rentals in Hillsdale

Secret Garden Short Stay

1 King Bed. 1 Twin air rollaway (plz req rollaway) Washer/Dryer for your use. Wi-Fi Fiber. Sep. fenced backyard area with Priv. entry into your bmnt area that is around the back of main house. Pking space on prop. walking trails. Pet fee is charged. Close to hwy, & shopping. Solar panels that provide some back up for the heat/air and refrig. Daylight bsmnt is sep from us upstairs with locked door. Couple of steps on path, none inside. Bsmt has had oder at times when previous guest cook etc.

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!

Cozy cottage getaway in garden paradise

Get away and relax in a whimsical octagonal cottage surrounded by a lush garden, overlooking a aqua pond and the Wakarusa river. You will have everything you need for a romantic date night or an inspiring place to slow down and reconnect with nature. •1 bedroom open living space with lots of natural light and beautiful views. • Coffee cart with microwave and electric burner and mini frig are provided. • Paddle boat at the lower pond & 2 disc golf nets available for fun. •NO PETS ALLOWED

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 Lone Oak

Reconnect with nature at The Lone Oak, part of our working cattle ranch. Enjoy the quiet of the country while you go fishing in the pond, spotting the wildlife, and stargazing at night from the hot tub. Just five miles from town, right off the blacktop, and three miles from Interstate 49. The top level is a 1900 farmhouse that has been renovated and could have another group staying in it. The walk-out basement is two years old and ready for you to have a relaxing, memorable get-away.

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.

Studio Guest House

Enjoy Southern OP in this quiet neighborhood. Our studio guesthouse has a full kitchen, TV, a new a/c/heater, and google fiber internet. In case you get lonely, we have 2 friendly dogs always looking for attention. We are about 45 minutes away from the Kansas City airport, Kauffman Stadium, Arrowhead Stadium, the KU main campus, and the Harry S Truman sports complex. We are 10-15 minutes from the Scheels soccer complex. Overland Park has plenty of Kansas barbecue and shopping.

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.

Chic Family Home with Fenced Yard

Welcome FIFA - can accommodate groups. Two AirBNBs side-by-side. Completely renovated and stylish, this home is perfect for families, groups. Enjoy walking trails and playgrounds just steps away. Sleeps 6 to 8 with 2 bedrooms, 1.5 baths, king and two full beds, plus finished basement. Conveniently located near Overland Park and Olathe sports complexes, making it ideal for baseball, softball, soccer tournaments.

Vine & Petal - A Cottage Retreat

IG Handle: @vine_and_petal Ready to escape the hustle and bustle of the city without compromising on amenities? Join us at the Vine & Petal cottage retreat where we invite you to relax and unwind. We are conveniently located 3 minutes from I-435, 8 minutes from I-70, and 10 minutes from Legends Shopping Center including the Kansas Speedway and Sporting KC. Photographers send inquiries only.

Brianna Wagon @ Isinglass Estate

Our Brianna Covered Wagon is set in its own secluded cedar grove with your outdoor kitchen and private firepit overlooking a beautiful private pond. Enjoy the lovely setting of this romantic spot in nature- just a short walk to our Winery Tasting Room and full restaurant and bar. Your bathroom window offers views of the morning horses in our 100 acre pasture.