Vacation rentals in Winfield

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Top-rated vacation rentals in Winfield

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

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Top guest favourite
A contemporary studio apartment is showcased, featuring a spacious kitchenette with white cabinetry and a granite countertop. A comfortable sofa is positioned next to a soft area rug, with a king size bed visible in the backdrop, complemented by light green bedding and wall decor.
Guest suite in Winfield
4.97 out of 5 average rating, 111 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

Top guest favourite
Home in Wichita
4.99 out of 5 average rating, 156 reviews

Speakeasy | Hot Tub | Plunge Pool | Fire Pit

Welcome to Crestline Ranch. This unique mid-century home is perfect for lovers of art, culture, and slow mornings with a good book. Collected worldly treasures and warm textiles set the tone, while a folksy speakeasy hides behind a bookcase. Soak year-round in the hot tub, gather by the firepit, or slip into the fully heated and cooled vintage camper for cards, cocktails, or an impromptu photoshoot. The stock tank pool opens Mid-March, cold plunge in spring and refreshing plunge pool in summer.

Top guest favourite
A two-story, red brick home is framed by autumn leaves, presenting a welcoming front entrance with a porch adorned with potted plants and a seasonal wreath. A concrete pathway leads to the front door, while a flag gently flutters on the side of the house.
Home in Douglass
4.99 out of 5 average rating, 109 reviews

The Vera Haus

Bring the whole family and enjoy this stunning piece of history with lots of room for enjoyment! “The Vera Haus” was built in 1921 as a wedding gift for Vera (Hartenbower) Blood from her groom Clarence Blood. The couple married Dec. 18th 1921. The home has its original quarter sawn oak wood work & doors throughout, oak wood floors, laundry chute, central vacuum, coal stove, the list goes on! Outside you can stargaze on the wrap around porch and enjoy the spacious corner lot & beautiful trees!

Top guest favourite
A modern kitchen is visible through an open-concept space, featuring gray cabinetry and stainless steel appliances. A breakfast bar with two wooden stools is positioned in front, while a small arrangement of flowers adds a touch of color. Natural light illuminates the area.
Home in Derby
4.95 out of 5 average rating, 173 reviews

Amanda’s Place

Relax with the whole family in this peaceful, cozy home with a private, fenced in back yard with outdoor games provided. Just a few blocks away you can enjoy tennis, pickle ball, a walk or jog along the Arkansas river, or display your skills at the Derby Skateboard Park. Within minutes be floating down the Rock River Rapids or checking out the Field Station; Dinosaur Park. Decarsky dog Park is a great place to meet new friends. Convenience stores, Fast food and restaurants are all close by.

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
A white, single-story cottage is positioned amid a grassy yard. A wooden deck extends from the entrance, adorned with potted plants. Large windows are visible, and a tree provides shade beside the home. The clouded sky reflects a calm and inviting day.
Cottage in Clearwater
4.99 out of 5 average rating, 212 reviews

Country Retreat in Fully Renovated Cottage

Clearview Cottage is a quiet country home just 13 miles from Eisenhower Airport and 20 minutes from downtown Wichita. This fully renovated home has one bedroom and one bathroom and is ideal for romantic getaways and business travelers. Outdoor spaces include a large front porch to watch the sunset and explore the stars at night. Located on a working farm, you will experience the sights and sounds of rural life and perhaps find some farm fresh eggs to enjoy!

Guest favourite
A spacious porch features a wooden swing adorned with plush cushions, complemented by a soft area rug. Sunlight filters through green foliage, casting gentle shadows on the floor. A fenced yard is visible beyond the railing, providing an open view of the surrounding greenery.
Home in Derby
4.82 out of 5 average rating, 469 reviews

Cozy cottage-like stay! In Derby!

Nestled safely at a quiet, dead-end road, right down the street from Madison Central Park in Derby, this cozy cottage-like stay features: -2 bedrooms/queen beds -1 bathroom -fenced-in backyard -updated WiFi with Roku TVs -large porch with porch swing -washer and dryer -new windows and carpet throughout home 8 miles to Kansas Star Casino! Please note: those aren’t comfortable with noise level (train in area) there will be noise machines available

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, 151 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 vacation rentals

When is the best time to visit Winfield?

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Avg. price$154 CAD$154 CAD$154 CAD$154 CAD$172 CAD$154 CAD$162 CAD$172 CAD$189 CAD$169 CAD$172 CAD$172 CAD
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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 vacation rentals in Winfield

  • Total vacation rentals

    Explore 30 vacation rentals in Winfield

  • Nightly prices starting at

    Winfield vacation rentals start at $84 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,880 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Winfield vacation rentals include wifi 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

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