Holiday houses in Winfield

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Top-rated holiday rentals in Winfield

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

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Top Guest favourite
Guest suite in Winfield
4.97 out of 5 average rating, 112 reviews

Lakeshore Escape Studio Apartment

Come and relax in this contemporary, impeccably clean studio apartment located in a quiet, charming neighborhood just minutes from downtown historic Winfield, KS. Nestled on 1.5 acres less than a mile from the Walnut River this location offers a beautiful scenic view and is perfect for guests who appreciate the outdoors. Explore the fun activities Cowley County has to offer including Island Park, Antiques, music Festivals, an more. Note: We are unable to host animals of any kind due to allergies

Guest favourite
An open staircase with wooden steps leads to an upper level, framed by a modern metal railing. Natural light filters through large windows, illuminating a stylish seating area with a circular coffee table and a plush sofa, creating an airy and inviting atmosphere.
Home in Winfield
4.95 out of 5 average rating, 19 reviews

The Point on 11th

The Point: Retro Cool, Modern Luxe in Charming Winfield, KS! Step into architectural brilliance at The Point, a unique 1970s post-modern house, exquisitely transformed by an extensive renovation. Marvel at its stylish roofline before unwinding in an amazing, deeply comfortable interior designed for ultimate relaxation. This is an experience. The Point is your chic base to explore a town rich in history, vibrant arts, and the famous Walnut Valley Festival. Book your unforgettable escape today!

Top Guest favourite
Condo in Winfield
5 out of 5 average rating, 59 reviews

Relax Restore Renew in Winfield

This beautifully decorated 1 bedroom/2 bath luxury condo features 1600 sf open layout. High end finishes including stainless appliances, granite counter tops, walk in shower, laundry room, whirlpool bathtub and smart TV. Just downstairs you will enjoy spa amenities, complete with a walk-in infrared sauna, massage, facials and much more! This place is close to everything, making it easy to plan your visit. This small quaint community features downtown historical whimsey you are sure to enjoy.

Superhost
A light-filled living area features a cozy arrangement of a sofa, love seat, and two ottomans, complemented by a mounted TV. Natural light streams through the windows dressed with sheer curtains, enhancing the welcoming ambiance. A dining table occupies one corner, adding functionality.
Home in Winfield
4.8 out of 5 average rating, 30 reviews

Charming Retreat with Style!

** Cozy, Stylish Escape in Winfield ** Welcome to your beautifully decorated home, perfect for a relaxing retreat. Enjoy the open, light-filled living area with a comfy sofa, love seat, chair with ottomans and a Roku TV, plus a fully equipped kitchen for all your needs. The master bedroom offers a plush queen-sized bed. Step out to a private backyard with a fire pit. Yard space galore for games and hanging out. Close to parks, restaurants and local attractions. This is your perfect getaway!

Top Guest favourite
The front view of a charming bungalow is displayed, featuring a welcoming porch with potted ferns and comfortable seating. Lush greenery surrounds the home, and steps lead to the entrance. The yellow exterior with brick accents adds to the inviting character of the residence.
Bungalow in Winfield
5 out of 5 average rating, 322 reviews

Lynn St Bungalow

Charming two bedroom, two bath bungalow built in 1925. All original wood floors. Existing bath completely remodeled with a deep antique bathtub with shower. Bathroom with a walk-in shower en suite to master bedroom which is the "Bluegrass Room". The "Sunflower Wheat Room" is slightly larger with king beds in both bedrooms. Fully stocked kitchen with basic cooking supplies provided. Security system with keyless entry. TV with DVD in living room and smart TV's in both bedroom & WiFi.

Top Guest favourite
The charming entryway features a covered porch with decorative railings, flanked by vibrant yellow flower boxes. A cozy bench with colorful cushions invites relaxation, while well-maintained grass and trees provide a serene outdoor setting.
Farm stay in Wellington
4.97 out of 5 average rating, 467 reviews

Conveniently located, yet still in the country

Country charm. Convenient location on highway 81 south of Wellington. Drive is large enough to accommodate trucks with trailers, moving vans etc. Fenced yard. Fully equipped kitchen: stove,small oven,micro, dishes, utensils, coffee pot. Coffee & filters provided. Games, books,music. Outside seating to watch sunrise and sunsets. Horse,donkey,poultry, cows (seasonal) on site.Close to Wellington,South Haven,Winfield, Oxford,Belle Plaine. Relax, Rejuvenate, Reconnect. (7 Day Max Stay)

Top Guest favourite
The exterior of a charming blue bungalow is shown, featuring a welcoming front porch with a ramp for accessibility. A path leads to the front door, surrounded by well-maintained landscaping and blooming white flowers. Large windows allow natural light to fill the space.
Home in Winfield
4.97 out of 5 average rating, 65 reviews

Cozy Blue Bungalow near College

Kick back and relax in this charming, stylish space, two blocks from Southwestern College. Newly updated 1907 Bungalow with original hardwood floors, fresh paint, farmhouse sink, and vintage charm throughout. Offering 3 bedrooms and newly renovated bathroom with claw foot tub/shower combo. Cable, Wi-Fi, & full size washer/dryer provided. Private backyard with gazebo & fire pit. New propane grill for cookouts. Front porch ramp for easy access. Private driveway parking available.

Guest favourite
A cozy living area showcases a mixture of seating, including a leather sofa and two armchairs. Colorful abstract paintings adorn the walls, along with several guitars. A round, patterned ottoman is positioned on a soft area rug, creating an inviting space filled with natural light.
Home in Winfield
4.98 out of 5 average rating, 84 reviews

Southwestern Cottage

This house is located in North Winfield, and is just a few minute drive from the Walnut Valley Festival. It's within walking distance of Southwestern College, The Kansas Veterans Home, and Cumbernauld Village. It's a quiet and safe neighborhood with some great opportunities to see wildlife like deer and turkeys while taking short walks close by. There is a garden and a screened in porch. The screen porch has a very nice queen futon, and has a great view of the garden.

Top Guest favourite
The exterior of the house is displayed, featuring a welcoming front porch and a sloping roof. Lush green shrubs border the pathway, with potted plants adding a touch of color. The entrance is accessible and leads to a charming interior.
Apartment in Winfield
4.98 out of 5 average rating, 203 reviews

College Hill Cottage in Winfield--Entire apartment

Located in Winfield's College Hill neighborhood, the first floor apartment is walking distance to Southwestern College, Grace Methodist Church, and College Hill Coffee, and a short drive everywhere else in town. Built in 1885, this house combines antique charm with modern comforts. KING bed in the main bedroom, QUEEN bed in the second bedroom, and a rollaway cot available. New carpet and newer furnishings throughout.

Top Guest favourite
A cozy living room is presented, featuring two comfortable sofas positioned around a coffee table. A flat-screen TV is mounted above a stone fireplace, which is framed by built-in shelves filled with books. Natural light enters through a large window with curtains.
Home in Winfield
4.99 out of 5 average rating, 166 reviews

Kozy Landing

Relax with the whole family at this peaceful place to stay. Great location, cozy, & clean! This charming unique 2 bedroom bungalow provides comfort and relaxation while staying in Winfield. This home has lots of character and newly refinished hardwood floors. Fully furnished with wifi and tv. Parking will not be a problem with the drive way and street parking in front. Includes a large fenced-in back yard and patio.

Top Guest favourite
The porch area features rustic wooden seating and a small side table, offering views of the open prairie. Cattle graze peacefully in the background, framed by trees under a clear blue sky. The spacious outdoor area provides a serene setting for relaxation.
Cabin in Latham
4.98 out of 5 average rating, 280 reviews

The Rock Creek Cabin

Cabin with rustic decor nestled in the Flint Hills of Kansas on the Rocking P Ranch. Enjoy life on the prairie: hiking, fishing a near by pond, and playing in the creek. Relax on the porch enjoying the view of the wide open space. BBQ grill, fireplace, and wildlife will make any season enjoyable. Only visitors you might have are the cattle and horses. Located just one hour from the Wichita airport.

Top Guest favourite
A tranquil Japanese-style garden features a pond adorned with lily pads and illuminated by string lights. A wooden walkway and a red bridge create a serene atmosphere, while lush greenery surrounds the scene, enhancing the garden's natural beauty.
Home in Winfield
4.95 out of 5 average rating, 152 reviews

Japanese garden home near coffee shop & college 🪴

Welcome to the garden home! The property includes a Japanese-style garden with a waterfall and pond. There is plenty of room for up to eight guests with a king and queen bedroom downstairs and 2 queen rooms upstairs. Both levels have a bathroom. We are conveniently located just blocks away from College Hill Coffee, Southwestern College, William Newton Hospital, and the public library.

Popular amenities for Winfield holiday rentals

When is the best time to visit Winfield?

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Avg. price$189 NZD$189 NZD$189 NZD$189 NZD$211 NZD$189 NZD$199 NZD$211 NZD$232 NZD$208 NZD$211 NZD$211 NZD
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Frequently Asked Questions

  • What are the best places to stay in Winfield?

    Stays in historic downtown Winfield, residential neighborhoods, or near parks are often suggested by visitors. These areas give easy access to local shops, eateries, and community events.

  • What are the best things to do in Winfield with kids?

    Kids enjoy playgrounds in city parks, visiting the local aquatic center, and participating in hands-on programs at area museums. Family-friendly events and seasonal festivals often include activities for children.

  • What are some of the best things to do in Winfield?

    Explore local shops downtown, tour area museums, or spend an afternoon in city parks. Music and arts events, community gatherings, and outdoor activities are often recommended.

  • How is the weather in Winfield?

    Winfield has chilly winters around 25–49°F (-4–9°C), and warm summers near 70–93°F (21–34°C). Spring brings rain and mild temperatures, making it a popular time for outdoor activities.

  • When is the best time to visit Winfield?

    Late spring and early fall are often suggested for milder temperatures and outdoor festivals. Summer brings music events and vibrant gatherings, while winter is quieter and suited to indoor explorations.

  • What are the best places to visit in Winfield?

    Historic downtown Winfield, local museums, and city parks are often recommended by visitors. Seasonal events and art venues provide opportunities to experience the community's creative energy.

  • What are some hiking trails in Winfield?

    Winfield has accessible trails in local parks, with paths suitable for a stroll or casual hike. Nature areas around the city feature walking trails bordered by native prairie plants and woodlands.

  • What are some family activities we can do in Winfield?

    Winfield has parks with playgrounds, local museums, and a community aquatic center that families often enjoy. Seasonal events and arts programs create welcoming activities for all ages.

  • What are some of the best day trip ideas from Winfield?

    Explore nearby small towns for antique shops, visit nature preserves, or experience lakeside recreation just outside Winfield. Regional museums and locally rooted art spaces are frequently suggested for a day excursion.

  • Are there any pet friendly accommodations available in Winfield?

    You will find pet friendly vacation rentals around central Winfield and neighborhood areas. Many hosts indicate whether pets are welcome, so it is easy to filter for stays suited to traveling with your companion.

  • What are some local tips for visiting Winfield?

    Locals enjoy exploring the historic downtown, attending community events, and sampling regional barbecue. It is wise to check for festival schedules and bring weather-appropriate clothing for changing Kansas skies.

  • What is Winfield known for?

    Winfield is recognized for its music heritage, especially the Walnut Valley Festival, and its historic downtown. The city is also known for welcoming community events and locally rooted traditions.

  • What are the best hidden gems to explore in Winfield?

    Winfield has smaller art galleries, quiet walking trails in neighborhood parks, and locally owned cafes that showcase regional flavors. Historic landmarks and community murals add unexpected interest around town.

  • What are the best foods to try in Winfield?

    Classic Kansas flavors are popular—smoked barbecue, hearty meat dishes, and locally rooted pies. Diners and cafes often feature homemade specialties, while seasonal festivals highlight regional foods.

  • What should I bring for a trip to Winfield?

    Pack comfortable walking shoes, layered clothing for changing temperatures, and sun protection. A reusable water bottle is useful for outdoor activities, and a rain jacket can be handy during spring and early summer.

  • What is the nightlife in Winfield like?

    Winfield's nightlife centers on relaxed bars, live music venues, and local restaurants with evening gatherings. Downtown is known for its music-forward scene, and community events sometimes extend into the evening.

  • What are the most popular events or festivals in Winfield?

    The Walnut Valley Festival draws crowds in late summer with music, workshops, and camping traditions. Local fairs, art walks, and holiday parades are also frequently suggested community gatherings.

  • Are there family friendly vacation rentals in Winfield?

    Many vacation rentals in Winfield have amenities suited to families, including multiple bedrooms and open living spaces. Properties near parks and downtown make it easy for families to enjoy local activities.

Quick stats about holiday rentals in Winfield

  • Total holiday rentals

    Explore 30 holiday rentals in Winfield

  • Nightly prices starting at

    Winfield holiday rentals start at $103 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,880 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Winfield holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Winfield rentals

  • 4.7 Average rating

    Winfield stays receive an average rating of 4.7 out of 5 from guests

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  2. United States
  3. Kansas
  4. Cowley County
  5. Winfield