Vacation rentals in Winston

Riverfront Boho Penthouse-Loft•Jacuzzi•Balcony

The perfect place to unwind! Master room boasts a super comfy king bed, a stylish built-in wall dresser, cozy fireplace, as well as a riverfront balcony. The 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!

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.

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!

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.

San Vincente Lake Cabin and 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.

McGaughy Place: *Rest *Relax *Renew

Escape to McGaughy Place! A charming 1 bedroom retreat offering comfort, convenience and small-town charm. Features a cozy living area, fully-appointed kitchen & well-designed bathroom — perfect for unwinding. Situated in historic Hamilton, MO. Centrally located behind the MSQ retreat. Close to outdoor recreation, boutique shopping, Lakeview Golf, and delicious local restaurants. Enjoy the tranquility of Hamilton with the convenience of being 60 minutes from downtown Kansas City and MCI.

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 the FIFA World Cup 2026 action in Downtown KC. Enjoy a 150" projector with a popcorn machine—perfect for movies or the big game! Amenities include high-speed Wi-Fi, karaoke, ping pong, and a 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!

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!

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

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!

Remote Cabin on Antler Ridge

Spend a weekend in the country! 1,300 sq ft cabin that is associated with country relaxation plus 230 Acre Missouri conservation lake! This area is perfect for all of your outdoor interests. Excellent accommodations will appeal to any small group outing to include fishing, duck hunting, deer hunting (archery, crossbow & muzzle loader), camping, hiking or just those that want to get away to a remote country setting.

Main Street Inn

The Main Street Inn is a darling little house right on the sleepy main street of Hamilton. You can see the Missouri Star Quilt Company from the front porch, which is important when you need that one last yard of fabric to finish your project. This is the creative project of Jenny and Ron Doan. We've put a lot of thought into making this a peaceful, convenient spot for quilters and creatives to enjoy.