Holiday houses in Winchester

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Top-rated holiday rentals in Winchester

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

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Top Guest favourite
Three horses graze on lush green grass under a glowing sunset. The sun casts a warm light across the landscape, creating a serene backdrop. A dog is visible nearby, adding a friendly element to the peaceful countryside scene.
Farm stay in Weston
4.93 out of 5 average rating, 389 reviews

Hippie Hills-FIFA World Cup 2026 near Kansas City

FIFA World Cup Visitors: We speak Dutch, German & Swiss German. LGBTQ friendly. Like a storybook, but with Wi-Fi, a hot tub, and a hospitality crew. Dogs Taco, Ally, and Bullet greet you at your car, frisbee in tow and zero chill. Donkeys Slim and Shady expect breakfast negotiations, while cats Potato and French Fry judge from afar. Horses Pieces and Jasper love head scratches. Historic Weston is 5 minutes away with shops, wineries, and charm. After exploring, unwind in hot tub under the stars.

Top Guest favourite
A well-lit bedroom features a spacious bed with a grey quilt and a second smaller bed, both flanked by bedside tables and lamps. Artwork depicting cowboys adorns the walls, and natural light filters in through a window covered by curtains.
Home in Ozawkie
4.97 out of 5 average rating, 121 reviews

Bunkhouse

♥️Perry Lake ,Ozawkie KING BED. Attention outdoor enthusiasts! This 1800-square foot ranch features three bedrooms, two baths, and an open floor concept that is great for entertaining or kicking back after a long day on beautiful Lake Perry. ✔ 3 min.away from Old Town boat ramp and campground . ✔8 min to village green golf course 5 min crooked post winery. ✔Pet friendly, family reunion friendly. ✔8 beds, 2 bathrooms, 3 tvs. Free WiFi ✔big yard, corn hole boards. Boat parking/trailer .

Top Guest favourite
The exterior of the cottage features a green facade with a welcoming entrance. A decorative wreath hangs on the door, accompanied by seasonal decor on a shelf. A vibrant red wagon and wooden seating are visible, along with a stylish wooden privacy screen and a covered entry area.
Tiny home in Tonganoxie
4.99 out of 5 average rating, 388 reviews

Kathy's Kottage (near Legends)hot tub-fire pit

First of - Kathy’s Kottage offers a uniquely private, warm and inviting detached cottage. We are not a huge commercial venture, but owned, operated, maintained, and cleaned by hosts who live within 150 yards. The Kottage is our only offering. We charge a cleaning fee of $35 a stay, so there isn't a list of chores at check out. We take up to 4 hours between every stay to extensively clean and disinfect every surface. We are proud of the Kottage as shown in every review over the last four years.

Guest favourite
An outdoor seating area is set in a spacious yard, featuring red benches arranged around a fire pit. A brick home with a sloped roof and front porch is visible in the background, surrounded by shade trees and green grass.
Farm stay in Auburn
4.9 out of 5 average rating, 372 reviews

Charming Farm Retreat Near Topeka, KS

🌾 Escape to Hidden Hill Farms, just 20 minutes south of Topeka! Our 4‑bed, 3‑bath farmhouse sits on an 80‑acre working farm with shady cottonwoods, a spacious deck, cozy fire pit, and peaceful countryside views. Families love our hands‑on farm tours—feed chickens, collect eggs, and meet the cattle. Inside, enjoy a fully stocked kitchen, Wi‑Fi, streaming TV, board games, and family‑friendly amenities. Perfect for reunions, retreats, and multi‑generational getaways filled with lasting memories.

Top Guest favourite
Bungalow in Kansas City
4.96 out of 5 average rating, 447 reviews

Tiki Lounge & Spa Day: Pool | Sauna | Cold Plunge

A 125-year-old bungalow packed with personality. Inside you’ll find curated worldly décor, many lounge spaces, and the house’s most famous feature: the Lucky Kitty Tiki Lounge, a hidden bar built inside the old garage. Outside, relax in the barrel sauna, cold plunge, and stock tank pool, gather around the fire pit, and unwind under the string lights after a night exploring Kansas City. It’s a one-of-a-kind stay just minutes from downtown, the stadiums, and some of the city’s best restaurants.

Top Guest favourite
The cabin showcases a rustic exterior with pine siding, surrounded by greenery. A spacious deck is visible, featuring outdoor seating, a grill, and a picnic table under a yellow umbrella. Large windows allow natural light into the home, enhancing the inviting outdoor space.
Cabin in Mayetta
4.99 out of 5 average rating, 143 reviews

Cozy Pine Country Cabin

Now to accompany our "barn style cottage"on the same property and all the same amenities and views of the great outdoors.You will fall in love with this spacious cabin from the first step you take into it ,with its high ceiling and three seperate sleeping areas.It comes with all the amenities of home with a great cabin feel.No pets allowed in the cabin but Ask us about boarding your dog in our climate controlled kennel on the property just a short distance from the cabin.

Guest favourite
A spacious jacuzzi is positioned against a large window, offering a view of the river and a vibrant sunset. The room features dark red curtains and wooden paneling, creating a cozy atmosphere. Lush green carpeting complements the serene setting.
Cabin in St. Joseph
4.89 out of 5 average rating, 223 reviews

Riverfront 2 BR Jacuzzi Cabin w/ Sunset Balcony

Forget your worries in this spacious 2 bedroom cabin located on the 2nd floor of this riverfront building! Enjoy a glass of wine in the jacuzzi while watching the river water pass by. Nestled just outside of town… a few blocks away, find new mountain bike trails. 2 miles away sits a casino, boat ramp, boat dock, conservation center, and a new riverwalk path that provides a peaceful path to historic downtown St. Joseph! Museums, great food, and amazing sunsets await you!

Top Guest favourite
A bright dining area is showcased, featuring a wooden table surrounded by four chairs. Large windows allow natural light to fill the space, offering views of the surrounding landscape. Floral centerpieces enhance the inviting atmosphere, while cozy seating is visible along the window ledge.
Home in Kansas City
4.98 out of 5 average rating, 461 reviews

Enjoy Nature at Modern Farmhouse Close to City

The perfect getaway that's close to it all! Enjoy your privacy at our restored 1933 bungalow on 18 acres just minutes off I-70. Relax after a road trip or gather your friends for a concert. Soak in the tub and get your best night of sleep on a plush mattress. Cook in a stocked kitchen or eat out at restaurants five minutes away. Meander along mowed paths, and let the kids play! We are pet-friendly, and business-ready with Gigabit Internet and an office setup.

Top Guest favourite
The farmhouse is set against a backdrop of rolling green hills and fields, with a pathway leading up to the inviting white structure. Trees frame the scene, and a horizon of distant hills can be seen under a sky tinged with soft evening colors.
Home in Atchison
4.94 out of 5 average rating, 108 reviews

Gracious Farmhouse with Beautiful Views

Gracious farmhouse on beautiful working farm offers opportunity for families to disconnect from city life. The farm has been in our family for 160 years; the house was built by our grandfather; Lewis & Clark camped on the land. The house is simply but comfortably furnished; all the mattresses are new. Enjoy family meals either in the dining room or on the enclosed porch. Doug and Bill farm the land so you may see them coming down the road.

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, 872 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 green sign for Crescent Moon Winery is prominently displayed. The sign features a distinctive logo and offers information about the tasting room hours. A vineyard is visible in the background, with rolling hills and a faint rainbow appearing above the landscape.
Home in Tonganoxie
4.94 out of 5 average rating, 193 reviews

Guesthaus at Crescent Moon Winery

This beautiful country setting is located on a paved road next to a producing vineyard and winery. The views of the countryside and pond are memorable. Enjoy a stroll through the vineyard and watch the grapes grow! If you book during harvest, you are welcome to help pick grapes watch them become wine! Our tasting room is open weekends or by appointment.

Top Guest favourite
An open and airy bedroom features a king-size bed with a light blanket and bedside tables with lamps. A comfortable chair is positioned near a window, allowing natural light to fill the space. Double doors provide access to the outside.
Cabin in Atchison
5 out of 5 average rating, 55 reviews

Cabin at Spring Meadow Farm

Come escape the hustle and bustle of life at this peaceful cabin nestled in the Kansas countryside. This amazing get-away location has fabulous views where you can relax and let go of all the daily stresses. We have also partnered up with a massage therapist, True Roots Massage, who can offer onsite massages to help you unwind. (Must book through her site)

Popular amenities for Winchester holiday rentals

  1. Airbnb
  2. United States
  3. Kansas
  4. Jefferson County
  5. Winchester