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.

Modern Loft w/ Brick Walls, Pool Table + Sleeps 12

You are going to LOVE the Lowman Loft - a beautifully refurbished historic building right in the center of Louisburg, Kansas. Only straight highway 40 miles from Kansas City. The loft is 3,000 sq ft. Open dining, living and kitchen areas and four private bedrooms. A perfect option for your friends, families, or workmates, the loft is located in a beautiful neighborhood surrounded by antique shops, local wineries, and wedding venues that you can explore. A short drive to Overland Park or Olathe.

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!

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.

Rantoul Wilderness Ranch On 440 Acres With Hot Tub

🌾 440 private acres in peaceful Rantoul countryside 🛏 4 bedrooms: 2 queen suites + 2 bunk-style queen rooms (sleeps 14) 🚿 4 ensuite bathrooms + additional full bath ♨️ Hot tub overlooking open Kansas fields 🎱 Game room with pool table, poker table & karaoke 🛶 Private fishing pond with kayaks & life jackets 🔥 Covered patio with fireplace & seating for 20 🍳 Fully equipped kitchen with large island 🥾 Private hiking trails & outdoor games 🚗 On-site parking + keyless entry

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! 🌱🌺🍂❄️

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.

Wade Ranch. Kansas Farm & Lake Stay. World Cup

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.

Chic Family Home with Fenced Yard

Stylish, comfortable and relaxing with fenced yard, this home is perfect for families and groups. Pets welcome. For more space the sister Airbnb is next door. 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.

The Pair Tree - A Romantic Retreat in the Trees

Escape to your own private retreat in the trees-where romance meets luxury. Nestled in the peaceful beauty of nature, this one-of-a-kind treehouse is the perfect hideaway for couples seeking connection, relaxation, and unforgettable memories. Surrounded by serene woodland views, you'll enjoy the perfect balance of tranquility and indulgence in a space designed just for two.

7‑Bed SE Olathe Home • Quiet Cul‑de‑Sac

Quiet SE Olathe cul‑de‑sac home with 7 beds, perfect for families and groups. Walk to parks and playgrounds. Upstairs has 3 bedrooms and 2 baths; the walkout basement adds a second living area, queen bed, trundle daybed, wet bar, and full bath. Enjoy a fully stocked kitchen with KitchenAid appliances, G‑Fiber internet, Roku TVs, washer/dryer, covered porch, and back deck.