Holiday rentals in Winston

Fall Family Fun at The Farm House! Pet Friendly

Our charming Farm House is a peaceful setting indoors and out! A great retreat from city living - perfect for gathering friends and family any time of the year! Comfortable beds, large living areas, lots of porch seating, beautiful sunsets, and access to the 3300 acre Pony Express Lake Conservation Area make this the perfect spot to unwind. Whether you're looking for peaceful surroundings, a private retreat, a place to play, or all of the above, The Farm House is the ideal choice for your stay!

Location · Family · Hospitality

The Esbeck Farmhouse

This farmhouse is the perfect place to kick back, relax and enjoy making memories with the people you cherish most. Spend your mornings admiring the wildlife or the cattle in the surrounding pastures and watching the sunrise from the front porch. Then, head out for a fun-filled afternoon with many attractions in the surrounding area from the Jameson, Hamilton, Jamesport and the beautiful sites of Lake Viking. Return home to fire up the grill and relax on the porch while enjoying good company.

Location · Family · Getting around

Retro Farm home 10 minutes to I-35 in country

1 Hour N. of Kansas City E. of St. Joseph 27 mi to Hamilton Charming retro farm home One mile on gravel off Hwy 6 I do my best to keep house clean, but sometimes there is dust, seasonal bugs beyond my control, as this is a farm. Come enjoy the simple life in this simple retro farm home. MAXIMUM OF 4 guest-including kids, this is a small home. If you’re looking to see stars & enjoy sounds of nature you’ll like this home with the view of sky. Dust control put on road in front of home.

Family · Location · Indoor spaces

Country Paradise •9 acres•Pool•Rec Center•5690sqft

Welcome to your very own private resort! As you approach the property, you'll be greeted by a beautiful farmhouse-style home that sits on 9 acres, with a 55ft wrap around deck offering sweeping views of the expansive grounds. Pool table, Ping Pong, Shuffleboard, Foosball, Air hockey, Nintendo & Switch. This property is a true gem for those seeking both space (5600 sq ft) & serenity. 17miles-airport, 20miles Downtown KC/ P&L District, 22miles-Chiefs /Royals Stadium, minutes to Smithville Lake.

Value · Location · Back garden

San Vincente Lake Cabin at SundanceKC

Our beautiful light filled cabin with wood-burning fireplace is perched above our spring-fed 15 acre private lake next to the common outdoor lounge area and sand beach. We have 200 acres of gorgeous property with limestone boulders and hiking trails throughout. The lake is great for swimming, kayaking, stand-up paddle boarding and offers excellent fishing. We are five minutes from downtown Excelsior Springs, Excelsior Springs golf course and 3EX municipal airport. Relax, rejuvenate and play.

Family · Location · Grill

Lovely 5 BR Home 1 Block to MSQC - Sleeps 12+

Our beautiful, restored historic home is located just one block off of Hamilton's bustling main street and within easy walking distance to Missouri Star. With five bedrooms, four bathrooms, 10 beds and lots of extra space, this home is perfect for families or groups to enjoy their time together. The large open kitchen, dining and family room are perfect for gathering, sewing, or making memories. Each of the rooms is equipped with all your needs for a relaxing and comfortable stay.

Family · Location · Walkability

Hamilton Getaway - 2 Bedroom House in DT Hamilton

Explore Hamilton, MO, the heart of Quilt Town USA (Missouri Star Quilt Co) and Let's Make Art, a haven for makers! This house, close to downtown, is ideal for families or friends seeking relaxation. Nestled in a tranquil neighborhood, it offers a perfect setting for evening strolls amidst fireflies and sunsets. ✓ Newly refurbished for a fresh ambiance ✓ Indulge in entertainment on a 55" TV ✓ Enjoy air-conditioned comfort ✓ Prime Location ✓ Complimentary WiFi ✓ Convenient free parking

Location · Family · Laundry

Touch of Country 150" projector, PingPong &Karaoke

Welcome! Relax at our hidden sanctuary, just 2 mins off I-35/Hwy 36 and 50 mins from Downtown KC. Enjoy a 150" projector with a popcorn machine—perfect for movies or the big game! Amenities include high-speed Wi-Fi, ping pong, Nintendo Switch, Karaoke and an outdoor grill. Explore our private oasis featuring a peaceful stream with a bridge and expansive green space. Free large parking with a pull-through driveway for trucks/trailers. Only 5 mins to groceries. Book your stay today!

Family · Location · Parking

Small town USA Airbnb

This small town is located not far from it all, just an hour North of Kansas City and 20 minutes from Saint Joseph, right between Interstates 29 and 35! Located on the ground floor with parking right outside the door on Main Street, this is a lovely place to stay. We also have plenty of extra parking next door. A nice park only a couple of blocks away. The bathroom features a walk-in shower and a full-size washer and dryer. The kitchen is furnished with everything you need!

Value · Location · Quiet

Lou Lou’s Lodge

Welcome to your cabin! It is a four-bedroom stay that accommodates up to 6 guests. This cabin is perfect for families or friend groups that are looking for a relaxing getaway. You will leave feeling refreshed! (New Build with landscaping & grass not yet completed) Inside: * 4-bedroom stay that sleeps 6 guests * 2 full bathrooms * Washer/dryer * Fully equipped kitchen * TV & wifi Outside: * Includes front & back deck * Contains gas grill * Multiple car parking

Location · Family · Outdoor spaces

Country Farmhouse

4 BR 1.5Bath home tucked away at the end of a quiet country lane, this peaceful retreat offers seclusion that’s hard to find. Surrounded by corn fields, pasture, deer and turkey, the home feels completely removed from the rush of everyday life. Perfect for couples, hunters, families, solo travelers, or anyone seeking a true escape, this secluded country home is an ideal place to slow down, reconnect, and enjoy the simple beauty of rural living.

Location · Indoor spaces · Hospitality

Modern Home in Gallatin

Reconnect with loved ones in this family-friendly place. Fenced in backyard with a private porch. Perfect for hunters, bridal parties, weekend getaways and family! Need more space for the whole family to be together?! Ask us about our other rental right next door! 15 minutes from Missouri Star Quilt 15 minutes from History Jamesport/Amish Country Dogs must be registered before stay! We charge a $50 pet fee per stay!

Location · Value · Wifi