Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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

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Top guest favourite
A well-lit bedroom features a spacious bed with a grey quilt and a second smaller bed, both flanked by bedside tables and lamps. Artwork depicting cowboys adorns the walls, and natural light filters in through a window covered by curtains.
Home in Ozawkie
4.97 out of 5 average rating, 122 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
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, 389 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
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
4.84 out of 5 average rating, 122 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 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
4.89 out of 5 average rating, 254 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

Guest favourite
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, 102 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 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
A spacious jacuzzi is positioned against a large window, offering a view of the river and a vibrant sunset. The room features dark red curtains and wooden paneling, creating a cozy atmosphere. Lush green carpeting complements the serene setting.
Cabin in St. Joseph
4.89 out of 5 average rating, 223 reviews

Riverfront 2 BR Jacuzzi Cabin w/ Sunset Balcony

Forget your worries in this spacious 2 bedroom cabin located on the 2nd floor of this riverfront building! Enjoy a glass of wine in the jacuzzi while watching the river water pass by. Nestled just outside of town… a few blocks away, find new mountain bike trails. 2 miles away sits a casino, boat ramp, boat dock, conservation center, and a new riverwalk path that provides a peaceful path to historic downtown St. Joseph! Museums, great food, and amazing sunsets await you!

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, 874 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
Home in Kansas City
4.94 out of 5 average rating, 297 reviews

Skyline | Hot tub | Rooftop Patio | Amazing Views

Hot tub, fire pit, rooftop patio and amazing views of the KC Skyline! Brand new home, with comfortable king size beds, 3 tv's and modern decor. Outdoor grill, picnic table, wood fire pit and rooftop gas fire pit. Hammocks, corn hole and board games. After booking, guests are required to complete a renter’s agreement and provide a valid government-issued photo ID prior to check-in. This is required for all guests without exception.

Top guest favourite
Treehouse in Perry
5 out of 5 average rating, 84 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 favourite
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, 194 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.

Top guest favourite
A uniquely shaped zome is presented, showcasing a grey façade with a distinctive yellow front door. Flower pots with vibrant blooms are placed on either side of the entrance. Lush green grass surrounds the structure, and a flag gently flutters in the breeze.
Dome in Baileyville
5 out of 5 average rating, 258 reviews

Zome on the Range

Featured in Ryan Trahan’s series “50 States in 50 Days!” Escape to rural Kansas and experience the unique charm of our 10-sided zome, located on a peaceful property near Baileyville. This countryside retreat offers a perfect place for relaxation and adventure, with a spacious interior, comfortable amenities, and stunning natural surroundings.

Popular amenities for Winchester holiday rentals

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