
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.

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.

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 .

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.

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.

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.

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.

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!

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.

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.

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.

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.

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
Other great holiday rentals in Winchester

Secluded Silo

Heritage House

The Bella on Broadway

Private guest house on 100 acre farm

Entire Home In Leavenworth

Two-bedroom cabin near Perry Lake

Great 4 bed cabin by lake

Quiet Acres in Oskaloosa KS
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- GEHA Field at Arrowhead Stadium
- Oceans of Fun
- Kauffman Stadium
- Kansas City Zoo
- LEGOLAND Discovery Center Kansas City
- Kansas City Convention Center
- The Nelson-Atkins Museum of Art
- Snow Creek Ski Area - 2022 OPEN WEEKENDS
- Legends Outlets Kansas City
- T-Mobile Center
- Jacob L. Loose Park
- University of Kansas - Lawrence Campus
- Negro Leagues Baseball Museum
- Overland Park Convention Center
- Midland Theatre
- Union Station
- Children's Mercy Park
- Overland Park Arboretum & Botanical Gardens
- Kansas Speedway
- Hyde Park
- Uptown Theater
- Kauffman Center for the Performing Arts
- Kansas City Power & Light District
- Crown Center





