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, 372 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
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, 341 reviews

Hippie Hills - Cozy Country Lodging and a Hot Tub

A whimsical retreat—like a storybook, but with Wi-Fi, a hot tub, and a greeting committee that takes hospitality very seriously. Dogs: Bear, Ally, and Bullet meet you at your car, frisbee/ball 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, MO, is 5 minutes away with shops, wineries, and history. After exploring, unwind in the hot tub under starry skies!

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, 359 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.

Superhost
The ranch-style home is set on a spacious corner lot, framed by large trees. A large driveway leads to a two-car garage and carport. The exterior features a mix of stone and wood, complementing the natural landscape.
Home in Leavenworth
4.95 out of 5 average rating, 138 reviews

Family, Business, Dog Friendly, Arcade and Toys

Three bedrooms (one queen and four twin), two tiled bathrooms, a twin-over-twin bunk and a sleeper-sofa. House sleeps nine comfortably. Six smart TV's. Dogs allowed! Large, fenced backyard. Two washers and two dryers. Basement is dedicated playroom and has a large arcade, pool table, skee ball, foosball, basketball machine, Barbie House and play kitchen. Dozens of board games and outdoor toys. Ultra-fast internet. Easy 20-minute drive from both from the airport and Legends Mall and Plaza.

Top guest favourite
A spacious living area is showcased, featuring a comfortable sofa and a coffee table. A flat-screen television is mounted on the wall. Soft lighting illuminates the space, which includes a kitchenette in the background with bar seating and wooden accents.
Guest suite in Dearborn
5 out of 5 average rating, 141 reviews

Berry Ridge Ranch-Cozy Guest Suite near Weston

Visit our acreage in the country nestled in the hills north of Kansas City - within minutes of KCI Airport (MCI), Weston, St. Joseph and Kansas City. Your experience starts with a tree lined drive, including evergreens, a fruit orchard, wild berries, native plant garden, trails, wildflower fields, solar array, wind turbine and a bonfire area among the trees. Nature galore! Lower finished basement level of our home - private, contactless stairway entrance. We can be ready on short notice!

Guest favourite
A cozy living room features hardwood floors and a flat-screen TV mounted on the wall. A dark leather sofa is complemented by a massage chair, and a wooden coffee table sits at the center. Table lamps provide soft lighting, enhancing the inviting ambiance.
Home in Lawrence
4.94 out of 5 average rating, 206 reviews

Disabled access king bed, massage chair, near I-70

This duplex is the perfect stop for a weary traveler! Sleep in a Big king-size bed or an adjustable queen bed! Garage to park in. This place is fully disabled accessible. One level, anti-allergen hardwood floors throughout. Walk-in shower with grab bars. Raised commode. For living room comfort,we provide a massage chair, power recliner sofa, Xbox Game system, and TV with premium channels on Roku! Kitchen is very open and fully stocked. 10 minutes from KU & downtown 5 minutes to i-70.

Guest favourite
A wooden entrance sign with 'Heartland Ranch' is positioned above a paved driveway. Lush green fields extend on both sides, with a car parked near the entrance. The sky features soft clouds, indicating a serene rural environment.
Farm stay in Wakarusa
4.85 out of 5 average rating, 477 reviews

Heartland Ranch, near Topeka, Kansas

Heartland Ranch is a short distance south of Topeka. Heartland Ranch, is quiet and private. We offer a unique country stay. This lodging is a cowboy bunkhouse with "down-home comfort" in a casual country setting. This is not a "Disney" experience and frankly the farm "stay" isn't for everyone! Occupancy is limited to your online reservation. Be sure to review Kansas Laws for alcohol age use or illegal drugs list. No firearms are allowed on the Heartland Ranch propert.

Guest favourite
A spacious studio features a comfortable bed, a colorful blue dresser, and a futon. A large wall map adds character to the room, while a flat-screen television is mounted nearby. Natural light fills the space through a window with a minimalist window unit above.
Guest suite in Ozawkie
4.91 out of 5 average rating, 110 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 spacious sleeping area is featured with a queen size Murphy bed folded down, covered in a striped duvet. Wooden cabinets flank the bed, and a mounted television is positioned above a simple shelf. Soft lighting enhances the neutral-toned walls and wooden floors.
Cabin in Oskaloosa
4.95 out of 5 average rating, 87 reviews

Dad's Country Retreat

  This small cabin was built for my father during the pandemic so he could spend time out in the country. Situated just off the highway on 5 tranquil acres it too can now be your weekend getaway.  Large enough for up to 3 people to stay if two sleep in the queen size Murphy Bed and the cot is set up in the sunroom. The space is best for 1 or 2 guests though. It is located very close to our neighbor so quiet is important. No pets, children, or smoking please.

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, 813 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
A bright living area features a modern couch adorned with colorful cushions. A small chair and table occupy one corner, and large windows provide natural light, offering views outside. A patterned area rug adds warmth to the space, enhancing the minimalist decor.
Home in Kansas City
4.95 out of 5 average rating, 975 reviews

Minimalist Modern Strawberry Hill Get-Away Home

Entire, separate entry, second floor studio. Minimalist modern decor, nice clean small space with everything you need. We aim to have your stay be an enjoyable experience, greeting you with a clean home, ensuring you have what you need during the stay, and being available as needed. Approximately 5-10 from downtown KCMO, Power and Light, City Market. Within walking distance of a few local family owned restaurants and bars.

Guest favourite
An open-concept kitchen is showcased with white cabinetry and stainless steel appliances. A large island with bar stools provides an inviting space for casual dining. Warm wood flooring enhances the bright atmosphere created by overhead lights and natural light from nearby windows.
Loft in Valley Falls
4.96 out of 5 average rating, 74 reviews

Brickstreet Downtown Loft

Spacious two bedroom two full bathrooms, open concept living and dining areas, full kitchen with laundry. Escape to this downtown, upstairs living. Beautiful exposed brick, plenty of room to kick back and relax. Located on Main Street and walking distance to the coffee shop, restaurant, city park, city pool, t shirt shop, and flower shop/ boutique. We can’t wait to share our quaint little town with you.

Popular amenities for Winchester holiday rentals

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