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
Guest favorite
A spacious sectional sofa in dark brown leather is positioned in a well-lit living area. A decorative blue area rug adds color beneath the seating. A side table with a lamp and small plants complements the comfortable setup, with a dining area visible in the background.
Home in Lawrence
4.91 out of 5 average rating, 187 reviews

Home Away From Home-3 bedroom 2 bath retreat

Enjoy ping pong or foosball in the attached garage. Take a nap in the comfy beds or relax on the soft sectional to watch TV. We are located 7 minutes from Walmart, Sprouts, or Dillons and 11 minutes from KU. Many restaurants are located nearby. You can eat at the picnic table in the fenced in back yard, or enjoy a burger made on the electric grill. On chilly evenings you can turn on the gas fireplace to stay extra warm. Four cars can fit in the driveway and there is space on the street too.

Guest favorite
The exterior of a spacious two-story house is viewed from the street. The front yard features a neatly manicured lawn and decorative stone landscaping. A split-level design showcases large windows, while a two-car garage with paneled doors adds convenience. A white picket fence borders the property.
Home in Leavenworth
4.85 out of 5 average rating, 131 reviews

Family, Pool, Toys, Business, Small Events, Pet

Large, spacious house perfect for sleeping up to twelve and entertaining up to twenty-five. One king, four queen and a full-over-full bunk bed. Three bathrooms. Dogs welcome! Scenic, fenced backyard. Fully stocked kitchen. Huge deck with BBQ grill. Real wood fireplace, firepit and firewood onsite. Two washers and two dryers for laundry. Five gig ultra-fast internet. Six smart Wi-Fi TV's. Full infant/toddler amenities. Several arcade systems, bins of toys, dozens of board games and activities.

Guest favorite
A spacious living area displays a comfortable gray sofa adorned with decorative pillows. A dining table is visible in the background, paired with wooden chairs. A kitchen with wooden cabinetry and a white refrigerator is located beyond. Natural light streams through the windows.
Guesthouse in Ozawkie
4.96 out of 5 average rating, 136 reviews

Rock Creek Loft Guesthouse neighboring Lake Perry

Voted one of the top Airbnbs to stay at in Kansas Imagine a serene setting walking distance to Lake Perry, just a 3 minutes walk to the Rock Creek Marina where you can boat, jet ski, or fish off the dock. 2 bedroom guest loft w/ Nest smart lock, private entrance, Starlink, fully equipped kitchen w/ open floor plan, Twinkle King mattress, 65” Satellite HD Smart TV, electric fireplace, washer/dryer, separate Nest central heat & air. Golfing, hiking, biking, ATV trails are minutes away.

Top guest favorite
The farmhouse features a grey exterior with white accents, set against a clear blue sky. A manicured lawn is complemented by pink flowers lining the entrance. A garage is attached, and the front porch is adorned with hanging planters.
Home in Oskaloosa
5.0 out of 5 average rating, 36 reviews

Quiet Acres in Oskaloosa KS

Quiet Acres is a two story lovely farmhouse in Oskaloosa KS. Surrounded by fields and yet close to the small town of Oskaloosa, enjoy the peacefulness of the country and also be close to the convenience of town. Quiet Acres sleeps 10 with four bedrooms and one air mattress. It has a fully equipped kitchen, a furnished living room, and all the other amenities you will need for your stay. Quiet Acres is also located close to the towns of Lawrence and Topeka, and is an hour from Kansas City.

Top guest favorite
Two sets of glass doors open to the indoor swim spa, framed by textured turquoise walls. A cozy seating area with a hanging chair and a small table is positioned nearby, along with greenery that adds a touch of nature to the space. Robes hang accessible on hooks.
Home in Eudora
4.97 out of 5 average rating, 119 reviews

The Cottage: Luxurious Getaway!

Escape to luxury at this private cottage with indoor 17-ft swim/spa, sauna, and steam shower. Sleeps up to 10 with beds, air mattresses, and convertible furniture. Enjoy a fenced patio, fire pit, robes, slippers, face masks, Nespresso, and more. Perfect for a romantic getaway, group stay, or small event (max 15). Includes kitchen, lounge areas, smart tech, and walkable access to downtown Eudora. No pets. Quiet hours 10p–8a. Swim at your own risk. Property is not child-proof.

Top guest favorite
A bright living area features large windows framing views of the surrounding nature. Comfortable seating includes a blue sofa with orange cushions and two accent chairs. A colorful area rug lies beneath a coffee table, enhancing the spaciousness of the room.
Earthen home in Perry
4.99 out of 5 average rating, 104 reviews

The Meadow - Modern Strawbale on 10 Private Acres

Take it easy at this unique and tranquil getaway. The Meadow house, a modern strawbale home, is surrounded by creeks and woodlands on ten secluded acres. Explore the surrounding woods, relax on the spacious deck and take in the stars, and plan adventures in nearby Lawrence and at Perry Lake Inside the home, curl up in a peaceful corner to enjoy a book, challenge family and friends to various games in the rec room, and enjoy meals from the modern kitchen with all the amenities.

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, 898 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 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, 403 reviews

Hippie Hills - Cozy Country Lodging and a Hot Tub

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. LGBTQ friendly

Top guest favorite
Tiny home in Perry
4.96 out of 5 average rating, 588 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. Set on 40 acres of beautiful wild woods and fields, cedar forests and ponds, 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!

Top guest favorite
Treehouse in Perry
5.0 out of 5 average rating, 106 reviews

The Pair Tree - A Romantic Retreat in the Trees

Escape to your own private retreat in the trees-where romance meets luxury. Nestled in the peaceful beauty of nature, this one-of-a-kind treehouse is the perfect hideaway for couples seeking connection, relaxation, and unforgettable memories. Surrounded by serene woodland views, you'll enjoy the perfect balance of tranquility and indulgence in a space designed just for two.

Top guest favorite
A charming studio cabin is displayed, featuring a sloped metal roof and a welcoming front porch. A bench with planters is positioned outside the entrance, which is framed by two lamps. The backdrop features trees and a clear sky with warm colors reflecting a sunset.
Tiny home in Ozawkie
4.96 out of 5 average rating, 67 reviews

Lakeview

A cute and cozy studio style cabin by the lake. Located 300' from the best Mexican restaurant/Latina grill in the area, which offers indoor dining, carry out along with a beautiful outdoor patio for dining and drinks. There is also a convenience store nearby.

Guest favorite
A scenic view of a working farm is captured, featuring a large barn and silos surrounded by lush green fields. A small pond reflects the clouds above, while trees line the background, contributing to the rural ambiance.
Farm stay in Tonganoxie
4.92 out of 5 average rating, 172 reviews

Tonganoxie Farm Stay

Perfect spot for your whole family to enjoy a peaceful country setting close to the fun of Kansas City and Lawrence activities.

Popular amenities for Winchester vacation rentals