Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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Top guest favourite
A spacious living area features original hardwood flooring and exposed brick walls. Comfortable seating options include a leather sofa and armchair. Large windows allow natural light to fill the room while potted plants add a touch of greenery to the inviting space.
Loft in Leavenworth
4.97 out of 5 average rating, 395 reviews

Follow Lincoln's Steps at Queenie's Loft in Leavenworth

Look out at the pristine City Hall with the Statue of Liberty and a bronze sculpture marking the city where Honest Abe visited just before announcing his run for Presidency. The original bricks and hardwood in this unique 170-year-old home have stood the test of time. Take a an elevator (or stairs) to the 2nd floor. Located in the heart of historic downtown Leavenworth, the First City of Kansas. Within a few blocks are several coffee shops, bakeries, boutiques, and bars. Located only 10 miles from the award-winning tourist town of Weston, which has many breweries, wineries, and hiking trails. You won't find this anywhere else! Original wide hardwood floors that were laid 165 years ago and the original brick walls that have stood the test of time. A view from nine windows that overlook our pristine city hall with the statue of liberty and statue of Abraham Lincoln. (Lincoln announced his run for presidency right there in Leavenworth!) And to think, he most likely walked across the street and came in our building as it was a saloon at the time! You will enter our loft from the street by keypad and there is a small room leading to our new elevator (big steel door) to take you to the 2nd floor. Directions for the elevator are on the wall. Very easy, just always close the white accordian door to elevator in case your party calls it from another floor. Your party is the only people who have access to this elevator. Check in is between 4 and 7pm. Please drop us a text if it is not in that time frame. Check out is 11am. Again, please drop us a text if you need more time! Mac and Stacy are always just a text away and can be there within 10 minutes. #913-651-7798. Text us with any questions! Ride a custom elevator to the open yet cozy space above the host's candle and gift boutique. The flat is a great base to explore KC, Fort Leavenworth, the county seat, and quaint Weston, MO. Shops, restaurants, coffeehouses, and bars are steps away. There is a large parking lot behind the building on 5th street. 65" tv, but we do not have cable. There is a dvd player, and you are welcome to hook your phone to the tv to watch your prime video, hulu, etc. That is what we do, and use the data from our phone or computer to display on the tv screen!

Top guest favourite
A hot tub sits invitingly, surrounded by a lush green landscape. Gentle bubbles rise from the water, offering a sense of relaxation. In the background, rolling hills and trees provide a picturesque setting under a clear blue sky.
Farm stay in Weston
4.93 out of 5 average rating, 381 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 cozy living area features a large brown sofa opposite a flat-screen TV. Wooden chairs are positioned around a circular table, and natural light comes through a nearby window. A star decoration adorns the wall, contributing to the relaxed ambiance.
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
A private outdoor space features a hot tub with a wooden cover, surrounded by a gravel area and bordered by a wooden fence adorned with decorative designs. A light blue chair provides a seating option next to decorative wooden panels.
Tiny home in Tonganoxie
4.99 out of 5 average rating, 383 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
Bungalow in Kansas City
4.96 out of 5 average rating, 434 reviews

Tiki Lounge | Sauna | Cold Plunge | Pool

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 octagonal cottage is surrounded by a well-manicured lawn and features a stepping stone pathway leading to a patio area. Large windows with shutters offer natural light, and a small air conditioning unit is visible on the side of the structure.
Guest house in Eudora
4.9 out of 5 average rating, 247 reviews

Cozy cottage getaway in garden paradise

Get away and relax in a whimsical octagonal cottage surrounded by a lush garden, overlooking a aqua pond and the Wakarusa river. You will have everything you need for a romantic date night or an inspiring place to slow down and reconnect with nature. •1 bedroom open living space with lots of natural light and beautiful views. • Coffee cart with microwave and electric burner and mini frig are provided. • Paddle boat at the lower pond & 2 disc golf nets available for fun. •NO PETS ALLOWED

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
Guest suite in Ozawkie
4.91 out of 5 average rating, 113 reviews

Rock Creek Studio Neighboring Lake Perry

Voted one of the top Airbnbs to stay at in Kansas & the most affordable! Fully equipped kitchen, stove, microwave, Starlink & 55' Roku Satellite HD TV, patio, & picnic area. Relax in our newly remodeled first floor studio nestled in the back of the guesthouse garage w/ separate private entrance. Located within a 3 minute walk to the Rock Creek Marina where you can kayak, fish, jet ski, boat or fish off the dock. Golfing, hiking, biking, ATV trails are minutes away.

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, 458 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
Cabin in Tonganoxie
4.96 out of 5 average rating, 868 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.

Guest favourite
The living room features a stone fireplace with an iron grate and a mounted flat-screen TV above it. Warm wooden walls complement a leather sofa and an ottoman, with natural light filtering through a nearby window.
Cabin in Vassar
4.95 out of 5 average rating, 107 reviews

Pomona Lake Front Cabin

Adorable 2 bedroom one bathroom cabin with a fireplace, large deck with hot tub, pretty view, good water frontage, nice flat yard and private dock to park your boat with a ladder for swimming. The cabin backs to pretty woods which provide peace and quiet, privacy as well as abundant wildlife. The lake is just 100 yards down a nice trail through the woods. A 3 person kayak is available for your use, as well as a fire ring and lawn chairs.

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, 582 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!

Popular amenities for Winchester holiday rentals

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