Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite

The cottage displays an octagonal shape with a black roof and large windows adorned with shutters. A stone pathway leads through the manicured lawn, surrounded by trees and boulders, providing a peaceful outdoor setting.

Guesthouse in Eudora

4.88 out of 5 average rating, 172 reviews

Cozy cottage getaway in garden paradise

Get away and relax in a whimsical octagonal cottage surrounded by a lush garden, overlooking a swimming 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

Home in Overland Park

4.97 out of 5 average rating, 120 reviews

South OP, 4 Bedroom, Game Room, 85” TV

Welcome 2025! Weekend Getaway or Business Trip. Stay at our amazing 4 bedroom/3.5 bath home, fully furnished with a mid-century modern vibe. Enjoy the Lower Level featuring an 85" TV, a beautiful wood Stiga ping pong table, and a game table (we even provide poker chips). BBQ grill on the patio. Pets are welcome. Fenced back yard. Fully stocked kitchen. Many extras offered to anticipate a comfortable stay. If you forgot to pack it - we have it! Convenient HWY access. Let us host your next visit!

Top guest favorite

An inviting dining area features a table set for six, accompanied by black chairs and natural placemats. A modern light fixture hangs overhead, while artwork adds interest to the wall. The kitchen area, visible in the background, showcases white cabinetry and contemporary appliances.

Townhouse in Lenexa

5 out of 5 average rating, 103 reviews

Art-filled Retreat w/ King Beds & Private Patio

Unwind at this art-filled, newly renovated townhouse minutes from restaurants, shopping and entertainment. Two king bedrooms with smart TVs make for a great getaway for two couples or a small family. Enjoy the fully-equipped kitchen or grill on the private patio. The basement serves as a lounge and office space and is equipped with a TV, sofa, desk, laundry room and full bath. Walk to the community pool or hit the courts for a game of basketball, tennis, or pickleball with provided equipment.

Guest favorite

A pool table is positioned in the foreground, with a sectional sofa and lighted wall accents creating a relaxed atmosphere. A doorway leads to a kitchen area visible in the background, characterized by bright lighting and modern cabinetry.

Home in Prairie Village

4.9 out of 5 average rating, 164 reviews

Spacious Luxury Retreat w/ Hot Tub & Movie Theatre

Relax and take a break in this spacious family retreat! Check out the great outdoor space with 8-person hot tub, firepit and quite patio. Relax inside on the 12' sectional and watch your favorite movie on a 150" screen! Little kids will love swinging on the back yard playset, or climbing on the 25' pirate ship and two-story castle! Pool table in the game room is great for all ages! All bedrooms feature plush bedding and high quality mattresses and smart TVs. Full kitchen cutlery and utensils.

Guest favorite

The exterior of a multi-level log cabin is displayed, featuring a combination of wooden siding and large glass windows. A fire pit is centered in the foreground, surrounded by a grassy yard. Two outdoor balconies are visible on the upper levels.

Cabin in St. Joseph

4.93 out of 5 average rating, 141 reviews

Penthouse w/ Boho Loft, Jacuzzi, + Balcony -3 bdrm

The perfect place to unwind! Master room boasts a super comfy king bed, a stylish built-in wall dresser, mock fireplace, as well as a riverfront balcony. Loft is great for lovers of Boho style, queen bed w/ ample space to stretch out for yoga as well as a private crow’s nest balcony! 3rd bed(twin) can be found in a repurposed library room. Take a dip in the jetted jacuzzi tub w/ a sunset view! A full kitchen awaits your cooking needs! Large private dressing/makeup room is a favorite!

Guest favorite

A bright living area features sleek gray sofas and a circular coffee table topped with decorative green spheres. A patterned area rug anchors the space, complemented by natural light streaming through the windows. A stylish staircase and separate dining area are visible in the background.

Home in Kansas City

4.89 out of 5 average rating, 28 reviews

Remodeled in Midtown - Hot Tub by Plaza & Downtown

Stay in the center of it all! This beautifully remodeled 1910 home is a perfect blend of historic charm with modern amenities in the heart of Midtown! Relax in the large hot tub in the privately fenced backyard. Enjoy the spacious living room and dining area for gathering. Grab a cup of coffee from the coffee station. Step in the quiet office nook. The kitchen is fully stocked. Minutes away from Downtown, Westport, 39th Street, and the Plaza. Quick drive to the stadiums and the airport.

Superhost

A spacious living area features a soft gray sectional sofa paired with a brown accent chair. A wooden coffee table sits atop a natural fiber rug. To the back, a dining table for four is visible, with a glimpse of a full kitchen in an open layout.

Loft in St. Joseph

4.82 out of 5 average rating, 126 reviews

Adorable, Cozy Loft Downtown St. Joseph

Great studio in downtown St. Joe. Walk to restaurants, bars, parks, and shops. Washer/Dryer, New King bed, full kitchen, new sectional sofa that pulls out into qn bed. 82” big screen..Everything you need! We are right next to Coleman Hawkins Park where many festivals and concerts are held. Check the St. Joseph downtown calendar for any events that might bring crowds and noise. We want your stay to be as enjoyable as possible. Unfortunately AirBNB doesn’t allow us to post the link here.

Guest favorite

A round dining table is set with four neutral chairs, each featuring warm tones. Decorative mirrors are mounted on the walls, reflecting natural light. A modern light fixture hangs above the table, providing illumination and a contemporary feel. The open layout connects to the kitchen area.

Townhouse in Mission

4.89 out of 5 average rating, 102 reviews

*Luxury Beds* Full Kitchen* Deck+Grill*

• Townhome • Garage available upon request ($) • One King BeautyRest Black mattress in upstairs Primary bedroom & one DreamBed Lux Queen Mattress in Guest • Outdoor private patio with BBQ • Fully equipped kitchen w/Keurig • Gigabit Internet (blazing fast) • Keyless entry access • Roku Smart TVs in all bedrooms (cable tv and local channels not provided) • Onsite, secure parking for 2 vehicles • Onsite washer + dryer available upon request-complimentary • Extremely safe neighborhood

Guest favorite

Home in Topeka

4.91 out of 5 average rating, 118 reviews

★Lake Sherwood ★ Large Families~ 5 Star Home ★

This beautifully remodeled private home is located in a quiet neighborhood. Topeka's premier neighborhood gives you comfort while your kids play in the fenced yard. You will be in the perfect location to get anywhere in less than 10 minutes. This great home sits in a lovely area with natural scenery. We have woken up many morning sitting watching the turkey and deer grazing behind our house. Easily accommodates a large group in a comfortable setting with good times for all ages.

Superhost

A hot tub is situated on a spacious deck, surrounded by comfortable seating. The skyline of Kansas City is visible in the background, showcasing an array of buildings against a soft sunset sky.

Home in Downtown Kansas City

4.79 out of 5 average rating, 144 reviews

Amazing House with Heated Pool & Rooftop Hot Tub!!

Experience an exceptional stay at our Kansas City vacation rental. Whether it's the stunning views, the year-round heated saltwater pool and hot tub access, or the top-notch furnishings and bedding; We have everything to make your stay unforgettable. Our well-appointed furnishings, bedding, and mattresses ensure your comfort during your stay. Come and enjoy the best that Kansas City has to offer! **3-night minimum on weekends/ 2-night minimum on weekdays/strict no-party policy.**

Top guest favorite

Home in Olathe

4.98 out of 5 average rating, 81 reviews

Treasure Chest- A boutique family getaway!

Make yourself at home among our treasures. Each room has its own theme to make your stay a truly unique experience. It is a collaboration of our past, present and future plans, as well as things we adore, places we've been, and ancestor's artwork. The bedrooms are inspired by our studies of history and interests this year; Mahatma Gandhi, Egypt and sushi! Check with us about how to host an event here!

Superhost

A bright living room is designed for relaxation, featuring a dark blue sofa accented with yellow pillows. A cozy white armchair is positioned nearby. A glass coffee table sits on a textured rug, and built-in shelves showcase decorative items. Natural light filters in through large windows.

Home in Kansas City

4.83 out of 5 average rating, 209 reviews

Beautiful 3 Bdrm Home Near Plaza | 19

Welcome to your ideal large-group getaway in this spacious West Plaza home! With three bedrooms, 2.5 bathrooms, a generous kitchen, dining room, and living room, there's ample space for family and friends to relax and reconnect. Experience comfort and convenience in the heart of Kansas City! This property is managed by Karat Vacation Rental Management