Holiday rentals in Winston

Our Happy Place

Take it easy and relax....a winding dirt path leads up to the cabin’s rustic porch, where a pair of wooden rocking chairs invite visitors to sit and soak in the breathtaking view of the sunset reflecting the sky’s shifting hues. At night, the stars shine brilliantly overhead, unobstructed by city lights, while the distant hoot of an owl adds to the peaceful ambiance. A firepit nearby provides warmth and a cozy spot for quiet evenings spent under a blanket of stars... 15 min. drive to Jamesport.

Value · Family · Cleanliness

Spacious 1 BR Carriage House - 2 min walk to MSQC

The Carriage House apartment is located above the detached garage of the historic home we've restored in Hamilton. The property is nestled one block between popular Main Street shopping (featuring the Missouri Star Quilt Co. shops) and the Missouri Quilt Museum. Everything is within easy walking distance from this beautiful, newly built apartment. Plus, you'll enjoy plenty of space, a full kitchen, free wi-fi and free laundry on site. We can't wait to welcome you to your home away from home!

Family · Value · Pets

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 · View

Robber's Roost Tree House at Beautiful SundanceKC Lake Retreat

Magical tree house nestled among oaks on our beautiful 200-acre national park-esque ranch fringed in gorgeous limestone boulders surrounding a spring-fed 15-acre private lake with outdoor living area and sand beach. Great for swimming, kayaking, stand-up paddle boarding and excellent fishing. We are 5 minutes from downtown Excelsior Springs, Excelsior Springs Golf Course and 3EX municipal airport. We live on-site and will generally be available throughout your stay should you need or desire.

Family · Value · Hospitality

Happy Hollyhock Hidaway

This non smoking home is on a quiet street in a great neighborhood featuring 3 bedrooms and 2 full baths. I made sure it has everything you will need for a home away from home. I cant stand going to an airbnb and not even finding a knife!! The whole group will enjoy easy access right off 36hwy in Cameron. Less than 2 miles away from restaurants and groceries. Great for a family or professionals. Lots of off street parking, corner lot with a big yard. Chiefs Training camp is 35min away!

Location · Check-in · Hospitality

Birdie's Nest

Welcome to your cozy cabin! This short-term rental features a front and back deck overlooking a scenic view. It is a three-bedroom stay that accommodates up to 4 guests. This cabin is perfect for singles or families that are looking for a relaxing getaway. You will leave feeling refreshed! Inside: * 3-bedroom stay that sleeps 4 guests * 2 full bathrooms * Washer/dryer * Fully equipped kitchen * TV & wifi Outside: * Includes front & back deck * Contains gas grill * Multiple car parking

Location · Kitchen · Quiet

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 · Walkability

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!

Family · Value · Nearby

The Cozy Camper: Boats, Fishing, S'mores and Beach

Hook a memory at our pondside gem! 🎣 Free perks: Campfire: Cook s'mores over a fire with a complementary s'mores kit! 🔥 Boats & Fishing: Cruise in paddleboats or cast away with our provided fishing poles! New playset for the kids!🛝 Wifi Included!📶 Fun built in beach for everyone!⛱️ Missouri Star Quilt Co. (15 Mins):You'll be at the world-famous "Land of Quilting" in no time! Jamesport (15 Mins):Charming Amish countryside, local bakeries, and handmade crafts

Location · Family · Biking

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 · Pets · Comfort

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 · Sleep quality

Quilters Getaway

This dreamy tiny home is the perfect getaway. Located just 8 miles from the Quilt Town of Hamilton. Featuring a twin size daybed/sofa on the main level and a full size bed in the loft. Kitchenette with microwave, coffee pot and refrigerator. TV with DVD player (and movies to pick from) and a nice selection of books. Located on a 1/2 acre lot with a park across the street and library a block away.

Family · Value · TV