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Vacation rentals in Winston

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Top-rated vacation rentals in Winston

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Top guest favorite
Farm stay in Maysville
4.97 out of 5 average rating, 143 reviews

10 drive from I-35 Cozy farm house

1 Hour N. of Kansas City 36 miles E. of St. Joseph 27 miles to Hamilton Charming retro farm home 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 retro, simple farm home. MAXIMUM OF 4 guest-including kids, since this is a smaller home unless approved. chickens live here & goats, sheep. If you’re looking to see stars & enjoy the sounds of nature you’ll like this home. Extra guest? Mesg me

Top guest favorite
A rustic cabin with a wooden exterior is surrounded by lush greenery. Large windows allow natural light to brighten the interior. A spacious deck is visible in front, with outdoor seating and a grill, offering a welcoming space for relaxation near the lake.
Farm stay in Excelsior Springs
4.95 out of 5 average rating, 310 reviews

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.

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, 179 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
4.86 out of 5 average rating, 102 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, 51 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!

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, 438 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!

Guest favorite
A four-poster bed is adorned with delicate white drapes and twinkling fairy lights, creating a soft ambiance. The bed features neutral-toned bedding, flanked by two bedside tables with lamps. The room is warmly lit, enhancing the inviting atmosphere.
Cabin in St. Joseph
4.97 out of 5 average rating, 117 reviews

Waterfront Sunset Cabin w/ Patio & Firepit- 2 bdrm

Forget your worries in this spacious 2 bedroom cabin located on the ground level of this riverfront building! Enjoy a sunset view of the river from the patio, living room, or the 2nd bedroom. Nestled just outside of town… a few blocks away, find new mountain bike trails. 2 miles away sits a casino, boat ramp, boat dock, conservation center, and a new riverwalk path that provides a peaceful path to historic downtown St. Joseph! Museums, great food, and amazing sunsets await you!

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, 249 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
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
4.9 out of 5 average rating, 126 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
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, 107 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 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, 175 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
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, 401 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