Holiday rentals in Winston

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Top-rated holiday rentals in Winston

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Top guest favourite
Farm stay in Maysville
4.97 out of 5 average rating, 145 reviews

10 minute drive toI-35 Cozy farm house World Cup

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

Guest favourite
Three horses graze on lush green grass under a glowing sunset. The sun casts a warm light across the landscape, creating a serene backdrop. A dog is visible nearby, adding a friendly element to the peaceful countryside scene.
Farm stay in Weston
4.93 out of 5 average rating, 350 reviews

Hippie Hills - Cozy Country Lodging and a Hot Tub

A whimsical retreat—like a storybook, but with Wi-Fi, a hot tub, and a greeting committee that takes hospitality very seriously. Dogs: Bear, Ally, and Bullet meet you at your car, frisbee/ball in tow, and zero chill. Donkeys Slim and Shady expect breakfast negotiations, while cats Potato and French Fry judge from afar. Horses Pieces and Jasper love head scratches. Historic Weston, MO, is 5 minutes away with shops, wineries, and history. After exploring, unwind in the hot tub under starry skies!

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
4.95 out of 5 average rating, 310 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, 180 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
4.96 out of 5 average rating, 447 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!

Top guest favourite
The entrance showcases a charming gray exterior with a light-colored door framed by vibrant flower beds. A small black chair is positioned beside the entryway, surrounded by lush greenery and colorful blooms, enhancing the inviting look of the patio area.
Tiny home in St. Joseph
4.98 out of 5 average rating, 174 reviews

The Nest(Tiny House) Private, Self Check-In, Wi-fi

400 sq. ft "tiny house" on edge of woods on private property with neighbors in view. Rural setting. Outside: green space and trees! Inside: cozy, cute, modern, and pleasing color palette. Well-lit spacious parking in driveway next to sidewalk leading to your patio. Here for a long weekend, wedding, or work? Perfect! 25-30 minutes to Atchison, Weston, & the K.C. Airport. Less than 5 minutes to St. Joe, gas, and food. Read on for more information regarding setting and amenities.

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, 251 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!

Top guest favourite
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, 129 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 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, 145 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, 168 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, 112 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.

Guest favourite
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, 403 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 holiday rentals

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