Holiday rentals in Winston

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Top-rated holiday rentals in Winston

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Top guest favourite
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
4.96 out of 5 average rating, 315 reviews

San Vincente Lake Cabin at 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 favourite
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.
Flat 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 favourite
The historic home features blue siding and white trim, framed by green trees. A welcoming front porch is adorned with hanging planters, and the fenced yard offers a touch of privacy. The entrance is marked by red doors, inviting guests to explore the interior.
Home in Liberty
4.95 out of 5 average rating, 455 reviews

Location! Upscale Historic home w/Chef’s Kitchen

Just steps off Downtown Historic Liberty Square, this updated 1890 home offers guests an upscale luxury experience. Be pampered in the comfortable master suite & enjoy a spa-like experience w/ large clawfoot tub, Carrera Marble shower. Chef’s kitchen includes many amenities. Enjoy meals at the large quartz island. Large private deck. Chaise couch in the living room. Home is divided into complete and private apartments. Each guest has their own entrance and no shared spaces. Wine included!

Guest favourite
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 favourite
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, 444 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!

Top guest favourite
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.
Guest house 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 favourite
Flat in Hamilton
4.91 out of 5 average rating, 11 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.

Top guest favourite
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 favourite
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.
Flat 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 favourite
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, 123 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 favourite
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 favourite
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.

Popular amenities for Winston holiday rentals

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  3. Missouri
  4. Daviess County
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