Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchester

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

1 of 1 pages1 / 1
Top guest favorite
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 favorite
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, 384 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 favorite
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, 385 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 favorite
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
4.91 out of 5 average rating, 367 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.

Guest favorite
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.
Guesthouse in Eudora
4.89 out of 5 average rating, 248 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 favorite
Barn in Lawrence
4.94 out of 5 average rating, 349 reviews

The Barn in The City.

NO CLEANING FEES. Take it easy at this unique and tranquil getaway. Cozy converted barn. Sleeping loft, NOTE: The sleeping loft has a maximum height of 5'1". very short walking distance to MANY bars and restaurants, 3 blocks from Allen Fieldhouse, near K.U. campus, just off K-10 and Hiway 59 junction. Off-street parking. 2 Amazon Fire T. V.'s with Wi-Fi, streaming and antenna T.V. Please Note: A 3rd guest will incur an additional charge of $35.00 A 4th guest is an additional $20.00

Top guest favorite
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 favorite
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, 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.

Top guest favorite
The studio features exposed brick walls and wood-paneled ceilings, creating a warm ambiance. Two sleek seating chairs are positioned in front of large double doors that provide natural light. A dining table is visible in the background, accompanied by a minimalist pendant light.
Guest suite in Downtown Kansas City
4.96 out of 5 average rating, 1,122 reviews

WestSide Brick Barn Studio

The Brick Barn Studio is a sweet and peaceful private space on the first floor of a late 19th century Carriage House. Guests enjoy private entry to their accommodation, mini kitchen, shower/bathroom, and laundry, king mattress on a unique built-in bench platform, and a convertible sofa for another guest or two. There is a privacy curtain provided for guests who would like a little separation between the bed and sleeper sofa.

Top guest favorite
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!

Guest favorite
A spacious living room features a large sectional couch arranged around a coffee table. Natural light filters through multiple windows, complemented by tall curtains. A flat-screen TV is positioned against the far wall, with a bookshelf and decorative cabinet nearby.
Apartment in Seneca
4.9 out of 5 average rating, 157 reviews

Downtown Loft Apartment

Cozy 1 Bedroom Apartment Overlooking Historic Downtown Seneca. Located above Sweet Pea's Bakery. Has a very spacious living room, with a sectional couch. With a smart TV, enjoy Netflix(please use the guest log in). There is also a DVD player and a few movies to enjoy. The Grocery store, bar, restaurants, and shopping all within walking distance. We offer free Kerig Coffee.

Top guest favorite
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, 190 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.

Popular amenities for Winchester vacation rentals

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