Holiday rentals in Hillsdale

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Hillsdale

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1

Guest favourite

A spacious living area showcases a dark sectional sofa paired with a light green armchair. Soft curtains frame the windows, allowing natural light to fill the room. A round coffee table sits on a textured area rug, enhancing the inviting ambiance of the space.

Home in Paola

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.

4.96 out of 5 average rating, 49 reviews

Top guest favourite

An open-plan dining and living area features a long dining table with black chairs. Off to the side, a cozy seating arrangement includes a sectional sofa and a coffee table. Natural light floods through large windows, and warm wood paneling creates a comfortable ambiance.

Loft in Louisburg

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.

4.97 out of 5 average rating, 75 reviews

Top guest favourite

Guest house in Louisburg

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!

4.96 out of 5 average rating, 160 reviews

Top guest favourite

The image features a modern cabin with wooden exterior, surrounded by lush greenery. A solar-heated swimming pool reflects the serene sky, with inviting lounge chairs positioned on a wooden deck nearby. Natural light highlights the architecture, enhancing the connection with the outdoor environment.

Cabin in Pleasanton

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.

4.93 out of 5 average rating, 30 reviews

Top guest favourite

Two sets of glass doors open to the indoor swim spa, framed by textured turquoise walls. A cozy seating area with a hanging chair and a small table is positioned nearby, along with greenery that adds a touch of nature to the space. Robes hang accessible on hooks.

Home in Eudora

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.

4.97 out of 5 average rating, 119 reviews

Top guest favourite

A welcoming two-story home is surrounded by a manicured lawn, featuring vibrant flower beds. Rocking chairs are positioned on a large front porch with hanging planters. The sun casts gentle shadows across the neatly trimmed grass, enhancing the peaceful outdoor setting.

Home in Cleveland

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.

4.97 out of 5 average rating, 144 reviews

Guest favourite

The spacious interior of the yurt features a patterned area rug in the center, surrounded by comfortable bedding on the floor. A wood stove with a visible flame is situated near a window, allowing natural light to enhance the space's cozy atmosphere.

Yurt in Paola

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! 🌱🌺🍂❄️

4.92 out of 5 average rating, 48 reviews

Guest favourite

An open living area features comfortable seating arrangements, including a leather recliner and plush couches. A patterned area rug lies beneath a wooden coffee table, with soft lighting provided by lamps on either side. A desk in the corner adds a functional workspace.

Townhouse in Spring Hill

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.

4.94 out of 5 average rating, 176 reviews

Guest favourite

Castle in Eudora

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!

4.95 out of 5 average rating, 38 reviews

Guest favourite

A historic farmhouse is surrounded by lush trees and expansive green grass. The house features large windows with dark shutters and a welcoming front porch, providing a serene atmosphere. Natural light highlights the exterior details of the home, blending with the surrounding landscape.

Farm stay in Paola

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.

4.97 out of 5 average rating, 37 reviews

Guest favourite

Townhouse in Olathe

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.

4.97 out of 5 average rating, 177 reviews

Top guest favourite

Treehouse in Perry

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.

5.0 out of 5 average rating, 105 reviews