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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
A spacious living area features original hardwood flooring and exposed brick walls. Comfortable seating options include a leather sofa and armchair. Large windows allow natural light to fill the room while potted plants add a touch of greenery to the inviting space.
Loft in Leavenworth
4.97 out of 5 average rating, 371 reviews

Follow Lincoln's Steps at Queenie's Loft in Leavenworth

Look out at the pristine City Hall with the Statue of Liberty and a bronze sculpture marking the city where Honest Abe visited just before announcing his run for Presidency. The original bricks and hardwood in this unique 170-year-old home have stood the test of time. Take a an elevator (or stairs) to the 2nd floor. Located in the heart of historic downtown Leavenworth, the First City of Kansas. Within a few blocks are several coffee shops, bakeries, boutiques, and bars. Located only 10 miles from the award-winning tourist town of Weston, which has many breweries, wineries, and hiking trails. You won't find this anywhere else! Original wide hardwood floors that were laid 165 years ago and the original brick walls that have stood the test of time. A view from nine windows that overlook our pristine city hall with the statue of liberty and statue of Abraham Lincoln. (Lincoln announced his run for presidency right there in Leavenworth!) And to think, he most likely walked across the street and came in our building as it was a saloon at the time! You will enter our loft from the street by keypad and there is a small room leading to our new elevator (big steel door) to take you to the 2nd floor. Directions for the elevator are on the wall. Very easy, just always close the white accordian door to elevator in case your party calls it from another floor. Your party is the only people who have access to this elevator. Check in is between 4 and 7pm. Please drop us a text if it is not in that time frame. Check out is 11am. Again, please drop us a text if you need more time! Mac and Stacy are always just a text away and can be there within 10 minutes. #913-651-7798. Text us with any questions! Ride a custom elevator to the open yet cozy space above the host's candle and gift boutique. The flat is a great base to explore KC, Fort Leavenworth, the county seat, and quaint Weston, MO. Shops, restaurants, coffeehouses, and bars are steps away. There is a large parking lot behind the building on 5th street. 65" tv, but we do not have cable. There is a dvd player, and you are welcome to hook your phone to the tv to watch your prime video, hulu, etc. That is what we do, and use the data from our phone or computer to display on the tv screen!

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, 163 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!

Top guest favorite
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, 340 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 favorite
The charming retro farm home is softly illuminated as dusk sets in, revealing a welcoming front porch with chairs. The surrounding area features trees silhouetted against the evening sky, and a gravel path leads towards the entrance, enhancing the tranquil ambiance.
Farm stay in Maysville
4.97 out of 5 average rating, 141 reviews

Farm Home 11 miles to I-35 Month 2 month rental

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. Heated by propane.

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, 308 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, 175 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
Home in Gallatin
4.76 out of 5 average rating, 25 reviews

Guest Home in Gallatin

Kick back and relax in this calm, stylish space. Small but mighty!! This home is perfect for couples or small families! Ask us about renting it with our larger home to fit the whole family! This home features 1 queen bed and 1 sofa bed! 2 twin beds available upon request! Please note this home does not have a full stove but is equipped with a table top double burner and a toaster oven. Home is located on the same property as another Airbnb and does share some outside common spaces.

Top guest favorite
A spacious living area is showcased, featuring a comfortable sofa and a coffee table. A flat-screen television is mounted on the wall. Soft lighting illuminates the space, which includes a kitchenette in the background with bar seating and wooden accents.
Guest suite in Dearborn
5 out of 5 average rating, 140 reviews

Berry Ridge Ranch-Cozy Guest Suite near Weston

Visit our acreage in the country nestled in the hills north of Kansas City - within minutes of KCI Airport (MCI), Weston, St. Joseph and Kansas City. Your experience starts with a tree lined drive, including evergreens, a fruit orchard, wild berries, native plant garden, trails, wildflower fields, solar array, wind turbine and a bonfire area among the trees. Nature galore! Lower finished basement level of our home - private, contactless stairway entrance. We can be ready on short notice!

Top guest favorite
An open living space features comfortable seating arrangements, including a reclined couch and a sectional. A large television is mounted on the wall, and a cozy area rug lies on the polished wooden floor. The kitchen is visible in the background with modern appliances.
Apartment in Stewartsville
4.95 out of 5 average rating, 44 reviews

Small town USA Airbnb

This small town is located not far from it all, just an hour North of Kansas City and 20 minutes from Saint Joseph, right between Interstates 29 and 35! Located on the ground floor with parking right outside the door on Main Street, this is a lovely place to stay. We also have plenty of extra parking next door. A nice park only a couple of blocks away. The bathroom features a walk-in shower and a full-size washer and dryer. The kitchen is furnished with everything you need!

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, 245 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 favorite
The exterior of the house features a light green façade with white trim and a welcoming front porch. A symmetrical arrangement of windows allows natural light to fill the interior. Lush greenery and stone landscaping enhance the inviting appearance of the home.
Home in Hamilton
4.98 out of 5 average rating, 160 reviews

Main Street Inn

The Main Street Inn is a darling little house right on the sleepy main street of Hamilton. You can see the Missouri Star Quilt Company from the front porch, which is important when you need that one last yard of fabric to finish your project. This is the creative project of Jenny and Ron Doan. We've put a lot of thought into making this a peaceful, convenient spot for quilters and creatives to enjoy.

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
4.91 out of 5 average rating, 93 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.

Popular amenities for Winston vacation rentals

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