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, 343 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.

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, 142 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 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, 478 reviews

Heartland Ranch, near Topeka, Kansas

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

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 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, 447 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, 815 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, 977 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.

Top guest favourite
A spacious living area features exposed brick walls complemented by bright curtains and a yellow sofa. A coffee table is centered on a patterned rug, while a dartboard is mounted on the wall. A bar area with stools provides additional seating.
Loft in East Lawrence
4.94 out of 5 average rating, 214 reviews

Industrial Escape - King Bed, Ground Level, 2/2ba

Experience urban living at its finest in our industrial loft in Lawrence's cultural arts district. Exposed brick, high ceilings, and modern amenities create a unique blend of charm and sophistication. Perfect for city explorers and culture seekers. Walking distance from Massachusetts street and close enough for a KU game! *New upgraded coffee/tea bar experience with hot chocolate and decaf coffee as well!

Top guest favourite
A newly remodeled kitchen features white cabinetry and modern stainless steel appliances, including a microwave, stove, and refrigerator. A small wooden table with two chairs is positioned nearby, providing space for meals. Natural light illuminates the warm wood flooring.
Home in Lawrence
4.98 out of 5 average rating, 179 reviews

Tidy tiny townhouse

Since January 2024. Rental license # STR-23-00057. Complete remodel. Everything is new. Visit Lawrence, KS on a budget. Duplex. 750 square feet of new everything. Watch movies on Netflix. Enjoy snacks, coffee, water, drinks. I want you to be comfortable and happy. - Completely renovated duplex - Keypad entry, keypad exit - Smart TV with Netflix, and wifi - Driveway parking - Cleanliness is #1

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, 557 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