Vacation rentals in Winston

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Top-rated vacation rentals in Winston

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Guest favorite
A cozy loft area features a queen bed surrounded by warm wooden beams. Decorative fairy lights create a soft glow. Colorful patterned cushions rest on a plush rug, with a small table and lamp complementing the tranquil ambiance. Ample wooden floor space allows for movement.
Cabin in St. Joseph
4.94 out of 5 average rating, 180 reviews

Penthouse w/ Boho Loft, Jacuzzi, + Balcony -3 bdrm

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!

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!

Top guest favorite
A cozy living area features a light-colored sectional sofa facing a large television set atop a light wooden entertainment unit. A decorative rug with intricate patterns is placed on the floor, while surrounding plants add a touch of greenery to the space.
Home in Hamilton
4.95 out of 5 average rating, 129 reviews

Beautiful 2 BR Cottage in Hamilton

Forget your worries in this spacious and serene home located just a quick drive from Hamilton’s quaint downtown. Whether you’re visiting family, shopping at Missouri Star Quilt Company, or attending a wedding at The Pearl, you’re sure to find everything you need for a wonderful stay. This newly remodeled home features a primary queen bedroom, a second bedroom with two twin beds, a spacious bathroom, fully stocked kitchen, and ample living and dining space. You’ll feel right at home!

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

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.

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!

Superhost
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, 122 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
A welcoming living room is visible through an open door adorned with a decorative wreath. A cozy seating area features an electric fireplace framed by a light-colored mantel, with a 50" TV and wooden furniture enhancing the space's comfort.
Home in St. Joseph
4.98 out of 5 average rating, 197 reviews

Welcome to Casa de Campo!

Welcome to Casa de Campo — your home away from home. Centrally located off the Parkway and near Highway 36, this designer-curated home offers style, comfort, and convenience. Just 5 minutes from Missouri Western State University and Mosaic Life Care, with nearby shopping, dining, and attractions, it’s perfect for work, campus visits, or a relaxing St. Joseph getaway.

Top guest favorite
A newly renovated gambrel-style barn features a combination of grey siding and large windows. A wooden bench is located on the porch area, and string lights are hung for illumination. Lush green grass surrounds the exterior, creating a tranquil rural setting.
Barn in Breckenridge
5 out of 5 average rating, 176 reviews

Relax in Rustic Luxury Overlooking Vineyard

A young vineyard planted in 2018, Catawba Vineyards boasts twenty acres of sprawling farmland property and a newly renovated gambrel-style barn to accommodate overnight guests and indoor/outdoor events. The property is currently developing and constructing its own wine-making processes to become the newest member of the growing north Missouri winery family.

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, 179 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.

Popular amenities for Winston vacation rentals

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