Holiday houses in Hillsdale

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Top-rated holiday rentals in Hillsdale

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Top 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
5 out of 5 average rating, 26 reviews

Over the Lake & Through the Woods. Fall Farm Stay

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, a working ranch, less than 30 minutes from Olathe, Kansas. Hunt, trail ride, boat, or fish. Near Wade Branch Boat Ramp at Hillsdale Lake and adjacent to 10,000 acres of Hillsdale Wildlife and State Park.Come find out why Wade Ranch is so special. A Registered Kansas Agritourism Ranch

Top Guest favourite
Guesthouse in Louisburg
4.97 out of 5 average rating, 119 reviews

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!

Top Guest favourite
A modern tiny home is nestled among lush greenery, featuring a large deck with seating. Glass doors open to the deck, offering views of a gentle stream. A stone path leads over a small bridge, connecting the home to the natural surroundings.
Tiny home in Bucyrus
4.93 out of 5 average rating, 40 reviews

The Cabin

Escape to tranquility! This tiny modern home, sits on a slow moving stream. The perfect blend of nature and luxury. Nestled on 20 lush acres surrounded by trees. Enjoy a full kitchen, washer/dryer, dishwasher & an outdoor fire pit. Private access to pool (staying guests only) , basketball court & a regulation pickleball court. Just 5 miles from the Bourgmont Winery & minutes to the Overland Park Arboretum. Kid tent party option , additional cost per guest. Horses do roam the open field.

Top Guest favourite
The exterior of a charming studio guesthouse is presented, featuring a white façade with decorative white trim. Two large windows and a door with a small wreath add to the inviting look. A black vehicle is parked in front, surrounded by greenery.
Guesthouse in Overland Park
4.99 out of 5 average rating, 175 reviews

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.

Top Guest favourite
A bright bedroom features a spacious bed covered with a patterned comforter. Natural light enters through a large sliding glass door that opens to a deck, complemented by a decorative window treatment. A small bedside table with a lamp adds to the room's functionality.
Apartment in Overland Park
4.95 out of 5 average rating, 182 reviews

1-bedroom 2nd floor suite w/private entrance!

We feature a smoke- and vape-free home and property. We also have a 2-bedroom listing. Leafy, close-in KS suburb. Apartment on 2nd floor of our home + DECK. Off-street parking for 1 car. Well-lit PRIVATE entrance. Microwave, mini-fridge, coffeemaker, kettle. Coffee, tea; Self-check-in for late arrivals. Very walkable neighborhood just 15 min. from Downtown, KU Med Center, Plaza, galleries, T-Mobile Center. Nearby locally-owned restaurants, coffee shops, parks, IKEA.

Guest favourite
A spacious reproduction Conestoga wagon is positioned on a gravel surface, with a covered outdoor kitchen nearby. The vibrant sunset paints the sky in warm colors, while the surrounding grassy area offers an open, tranquil setting for relaxation.
Farm stay in LaCygne
4.97 out of 5 average rating, 101 reviews

Covered Wagon1 @IsinglassEstate

Isinglass Estate is anything but ordinary. Our reproduction Conestoga Wagons have it all- with heat, A/C, a full bathroom, your own private outdoor kitchen and firepit, and five star details to complement the 100acre views of the polo field and vineyards! Wagon guests enjoy access to our 600 acre estate with fishing, hiking, vineyards, blackberries, a petting zoo, horseback rides, horse-drawn carriage rides, plus a restaurant and winery tasting room all on-site.

Top Guest favourite
A cozy sleeping area features a spacious bed with striped bedding and layers of soft blankets. A dark upholstered bench with textured throws sits at the foot of the bed. A bedside lamp provides soft lighting, and a decorative cabinet stands nearby.
Guest suite in Olathe
4.99 out of 5 average rating, 452 reviews

Secret Garden Short Stay

1 King Bed. 1 Twin air mattress roll away (plz req rollaway) Washer/Dryer for your personal use. Fast Wi-Fi Fiber. Sep. fenced off backyard area with Private entry into your basement area that is located around the back of the main house. Parking space on property. Dog park, walking trails. Restaurants close by. Close to highwy, gas stations and shopping. We also have Solar panels that provide some back up for the heat/air and refrig if electricity goes out!!!

Top Guest favourite
A newly renovated log cabin is surrounded by lush greenery, offering a tranquil entrance. A stone pathway leads to the rustic wooden door, while a picnic table is positioned nearby under the shade of a tree, enhancing the inviting outdoor space.
Cabin in Tonganoxie
4.96 out of 5 average rating, 821 reviews

Cozy Cabin Retreat

Escape to our cabin which earned top-rated Airbnb in all of Kansas for a cozy, quiet getaway. Ideal for unwinding and rejuvenating after the demands of a hectic day. Enjoy scenic hiking trails, axe throwing, horseshoes, or a peaceful walk through our labyrinth. End the day with a stunning sunset over the valley from our swing. Just 5 minutes from the lake! Note: The cabin is on a shared property with a retreat center, Sacred Hearts Healing.

Top Guest favourite
A tiny house made of wood stands surrounded by cedar trees, with a wooden deck leading to its entrance. A small table with two chairs is placed nearby, illuminated by hanging lights, providing a serene outdoor seating option.
Tiny home in Perry
4.96 out of 5 average rating, 561 reviews

The Batch - Tiny House Living

Located 20 minutes from downtown Lawrence, the Batch is a sustainable tiny house nestled in the cedar forests of Perry, KS. Decorated in a minimalist southwestern style, this tiny cabin is a serene and peaceful setting for souls seeking restoration, quiet, and the healing qualities of the woods. Or just a great place to getaway with your love or friends with an even greater view!

Top Guest favourite
A broad driveway leads to a spacious building featuring a mix of brick and blue siding. Two garage doors are visible, framed by landscaped green areas and decorative fencing. The serene surroundings are complemented by trees in the background, creating a peaceful entrance.
Barn in Greenwood
4.9 out of 5 average rating, 177 reviews

Cozy private cottage/studio

Private studio in resort-like property. Quiet neighborhood. Minutes from downtown Lee's Summit, Lee's Summit Hospital/Saint Luke's Hospital. Coffee shop/bakery within walking distance. Several restaurants close by, 1 mile to antique malls. Perfect place for traveling professionals.

Top Guest favourite
A charming bungalow exterior is displayed, showcasing a combination of light gray siding and dark roofing. Pathways lead to the entrance, bordered by landscaped areas. Sunlight casts shadows on the facade, highlighting the well-placed windows and a central chimney.
Bungalow in Louisburg
4.94 out of 5 average rating, 142 reviews

3 Acre Private Bungalow

Take it easy at this charming bungalow in Louisburg, KS. Nestled right near the downtown, but tucked away with a private, wooded backyard. This one-bedroom on 3 acres is the perfect escape just south of Johnson County.

Top Guest favourite
A large, modern numeral '2' is mounted on a subtly textured wall. The lighting emphasizes the number's sleek design, creating a focal point against the soft, neutral background.
Apartment in Ottawa
4.96 out of 5 average rating, 103 reviews

Old City Hall Apt #2

Spend a night or several in the renovated Old City Hall apartments - circa 1907. Close to downtown and Ottawa University. The Prairie Spirit and Flint Hills rail trails are easily accessible.

Popular amenities for Hillsdale holiday rentals

  1. Airbnb
  2. United States
  3. Kansas
  4. Miami County
  5. Hillsdale