Vacation rentals in Winston

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Top-rated vacation rentals in Winston

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Guest favorite
The front entrance of the cottage features a welcoming orange door framed by two windows. A festive wreath hangs on the door, and decorative potted plants are positioned on either side of the entryway. The pathway is lined with greenery, enhancing the inviting exterior.
Cottage in St. Joseph
4.92 out of 5 average rating, 443 reviews

Antebellum Cottage in Downtown St. Joseph, Mo.

JAN $50 Special! This charming cottage is a rare piece of history located in the historic Museum Hill District of St. Joseph Missouri. This delightful cottage is one of the oldest built homes in the district. Home was built in the 1860's & was the starter home for many newlywed couples during this era. Location of property is just a short stroll from downtown shops, restaurants & bars. If you are a historical enthusiast or just need a couples retreat this unique piece of history is a must stay!

Guest favorite
A bright, open kitchen and dining area features a round wooden table surrounded by four chairs. A white brick fireplace adds character to the space, while modern appliances, including a microwave and refrigerator, are neatly arranged in the kitchen.
Apartment in Excelsior Springs
4.94 out of 5 average rating, 184 reviews

The Suite Spot

Originally built as The Buckley Hotel, this historic building has been brought back to life. While retaining the features that makes this home so beautiful and reflective of its time, we have brought in modern amenities that insure a comfortable stay while in the heart of Excelsior Springs. This place is so perfect if you are visiting town as it's steps from shopping, eating and landmarks. The beds are comfy with nice linens because I, for one, love a good night's rest and I bet you do too!

Guest favorite
The exterior of the house features a contemporary design with smooth white siding and natural wood shingles on the front gable. The front porch is accessible via a concrete pathway, and two planters flank the entrance door, providing a welcoming touch.
Home in Hamilton
4.87 out of 5 average rating, 104 reviews

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

Top guest favorite
Home in Cameron
4.98 out of 5 average rating, 59 reviews

Touch of Country 150" projector, PingPong &Karaoke

Welcome to your quiet and cozy retreat! Get ready to unwind in this beautiful setting. Movie nights will be epic with our large 150-inch projector screen – just pop some corn in the provided popcorn maker and settle in for a cinematic experience. For some friendly competition, challenge your travel buddies to a game of ping pong. And when the mood strikes for some fun and laughter, unleash your inner pop star with our karaoke setup. We hope you have a wonderful and relaxing stay!

Top guest favorite
The kitchen and dining area feature modern stainless steel appliances and a table for four. A patterned rug adds texture to the space, which is illuminated by natural light from a nearby window. The minimalist design emphasizes functionality and comfort.
Guesthouse in Hamilton
4.97 out of 5 average rating, 255 reviews

Spacious 1 BR Carriage House - 2 min walk to MSQC

The Carriage House apartment is located behind 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!

Guest favorite
Apartment in Hamilton
4.89 out of 5 average rating, 9 reviews

Samuel Place: Rest * Relax * Renew

Escape to Samuel Place — a cozy, one‑bedroom retreat featuring a welcoming living room, a fully appointed kitchen, and a comfortable bath with shower. Enjoy a peaceful stay with access to charming local activities: MSQ, hunting or fishing, boutique shopping, Lakeview golf, plus a variety of restaurants, Ninja Moose Brewery, & visit JC Penney Museum! Conveniently located ~60 minutes from Kansas City, and Kansas City Int'l Airport (MCI), in historic Hamilton, MO.

Guest favorite
A spacious game room features a bright green pool table at its center, surrounded by comfortable seating. Wooden flooring and a ceiling fan enhance the open feel. A kitchenette with dark cabinets is visible on one side, providing convenience for guests.
Home in Smithville
4.89 out of 5 average rating, 136 reviews

Private peaceful very secluded!

The whole group will be comfortable in this spacious and unique space. Peaceful space in the valley where a rooster crow is all you hear in the morning. Have coffee on the dock while feeding koi in the koi pond! Off the beating path of traffic. Short drive to I 435 and I 35. About a half hour drive to Royals and Chiefs stadiums, downtown KC and Kansas speedway! Minutes from the bike and walking trails that circle Smithville Lake!

Top guest favorite
A cozy open living and dining area is depicted, featuring a dining table with wooden chairs. A comfortable sofa and an armchair provide seating options, with wall art accentuating the space. Natural light enters through the nearby window, creating a bright atmosphere.
Home in Chillicothe
4.97 out of 5 average rating, 151 reviews

Cute and convenient 2 bed 2 bath

Newly remodeled interior (we are still working on the outside!!) two blocks from Walmart and two blocks from Washington Street. Good parking on and off street. Wonderful open floor plan to host a family or just a comfortable place to stay. We are going to be as pet friendly as we can but please let us know if you are bringing pets (type, sizes and number) before booking. We have carpet in the front room and bedrooms. THANKS!

Top guest favorite
The exterior of a historic brick building is displayed, featuring large arched windows and a spacious balcony overlooking the street. A modern entryway is presented below, with a concrete path leading to the entrance. Dark clouds are visible in the sky.
Apartment in Stewartsville
4.99 out of 5 average rating, 170 reviews

Stewartsville's Downtown Airbnb

Completely furnished one bedroom apartment! Just a short hour drive North of Kansas City and 20 miles East of Saint Joseph! Located in the quant small town of Stewartsville. Two wineries and a working dairy (Shatto Milk Co.) close by. The bedroom hosts a spacious king size bed, and the living room has a pull-out queen sleeper sofa. Amenities include washer, dryer, Fast Wi-Fi and a 65" flat screen television.

Top guest favorite
The charming exterior of the tiny home is showcased, featuring a white wooden façade and a sloped roof. A small porch steps lead to the front door, with a single white rocking chair positioned nearby. Lush green grass surrounds the home, providing an inviting outdoor space.
Tiny home in Kingston
4.93 out of 5 average rating, 121 reviews

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.

Top guest favorite
The kitchen area is equipped with modern black appliances, including an oven and refrigerator. Grey cabinets with granite countertops offer ample storage and workspace. A dining table with seating is positioned nearby, complemented by decorative touches such as a potted plant and stylish runners.
Home in St. Joseph
4.96 out of 5 average rating, 178 reviews

Appealing 2 Bed/1.5 Bath Home in St Joseph

Enjoy your stay in this newly renovated , conveniently located 2 bedroom 1.5 bath duplex . Right off the north Belt highway, close to shopping , entertainment and restaurants. Easy access to I-29. Home has 2 - 65 inch smart TVs ready for you to login to your favorite streaming service. 1 Gig internet! Ready to handle all your entertainment or work needs.

Guest favorite
A spacious living area features a mix of leather seating arranged around a wooden coffee table. A stone fireplace serves as a focal point, with a nearby window allowing natural light. Warm lighting is provided by a floor lamp and ceiling fan.
Cabin in New Hampton
4.92 out of 5 average rating, 405 reviews

Wolf Den Lodge

This is a nice, rustic cabin located out in the country in a calm quiet atmosphere. Located a short drive from Bethany MO with access to everything you would need. There is plenty of countryside to explore as well as farm pond great for fishing about 100 yards from the back door. Great place to experience the country life and get away for a few days.

Popular amenities for Winston vacation rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Daviess County
  5. Winston