Vacation rentals in Maeystown

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Top-rated vacation rentals in Maeystown

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Guest favorite
A single-story home is set on a green lawn, featuring a light brown exterior and a neatly maintained pathway leading to the front door. Windows with red and white accents provide a welcoming touch, while trees line the background, offering a sense of privacy.
Home in Bloomsdale
4.91 out of 5 average rating, 247 reviews

Hop off the highway, Relax!

Relax with the whole family at this peaceful place to stay. We are located only 4 miles off of highway 55! There are two bedrooms and two COMFY couches if you have more than 4 staying the night! This is located on a secluded road with two other homes occupied nearby by with quite, but very friendly, residents. This home is 25 minutes away from the historical town of Ste Genevieve, take a look! The host is will be able to assist you almost immediately, whether it be over the app or in person!

Top guest favorite
A charming street scene captures the historic architecture of Ste. Genevieve. Colorful storefronts line the sidewalk, featuring a gallery and residences, while seasonal flowers add vibrancy. Trees with remaining leaves provide a natural canopy over the pavement, leading to parked vehicles in the distance.
Home in Ste. Genevieve
4.94 out of 5 average rating, 191 reviews

"Little Brick House" (Hael House built in 1865)

Best downtown location!! Take a trip back in time at this cozy, centrally-located brick cottage in historic Ste. Genevieve. The original home of John and Francesca Hael in the 1860's, you won't find a more authentic old town experience than you will get at "the little brick house" on Main Street. Enjoy mornings at the local coffee shops and bakeries (right across the street) and evenings on the back porch with a glass of wine. The Little Brick House has all the amenities with old world charm!

Top guest favorite
A view from the living area into the bedroom, showcasing a serene space with a queen-size bed dressed in crisp white linens and accented by earthy throw pillows. Natural light illuminates the room, complemented by a ceiling fan and light-toned wooden flooring.
Apartment in North Hampton
4.99 out of 5 average rating, 186 reviews

The Zen Den - Centrally Located, Calm and Tranquil

The Zen Den was conceptualized out of a desire to create a calm and peaceful oasis centrally located in the North Hampton neighborhood of St. Louis where parks, cafés, restaurants, and entertainment are only minutes away. The space features modern appliances, contrasted with soft light features and natural building materials, such as reclaimed lumber, to convey a sense of calm and tranquility. Ideal for those guests seeking to retreat at the end of a busy day exploring or remote working.

Top guest favorite
The historic stone farmhouse features a traditional design with multiple windows and a pitched roof. The exterior is complemented by grassy areas and a pathway leading to the front porch. Surrounding trees provide a natural backdrop, enhancing the rural setting.
Farm stay in Bloomsdale
4.96 out of 5 average rating, 163 reviews

FUNKS INN-no extra guest fees or cleaning fee

This house was built in 1870, it is a stone structure and was used as a family farm home. It has been remodeled for its use today. It is historically correct, which includes antiques of the time. Post Civil War era, furniture including the beds of this period. Another interesting aspect, is that the floors are all original. Mattresses, blankets pillows, bedding and towels are all new. The wine cellar that we have added, made on location. I always leave some out for guests. No fee.

Top guest favorite
The exterior of a chalet is illuminated at night by warm string lights. Large windows reflect soft interior light, revealing a cozy atmosphere. The wooden deck is accessed by a railing, creating a welcoming entry. Trees are visible in the background, adding natural charm.
Home in Dittmer
4.96 out of 5 average rating, 561 reviews

Honeymoon Suite at Camp Skullbone In The Woods

Experience a romantic, quiet, and cozy chalet designed for two! This charming retreat features vintage décor and all the modern amenities you need for a comfortable stay. Unwind indoors by kicking back and watching a movie, surfing the web, curling up with a good book or a friendly board game, or sharing a drink with that special someone. In the evening, relax on the cozy deck under the stars, basking in the warm glow of the gas fire pit or unwinding in the inviting private hot tub!

Top guest favorite
The treehouse structure is elevated, supported by stilts, with large windows that reflect the surrounding greenery. The exterior features a combination of wood finishes, and warm lighting casts a welcoming glow in the evening. The pathway leads through the natural landscape to the entrance.
Treehouse in Perryville
5 out of 5 average rating, 669 reviews

TreeLoft - Christmas in the Trees

The TreeLoft is a custom built luxury treehouse for two nestled in the eastern part of the Ozark Mountains. Enjoy the gas fireplace for a cozy evening ambiance, a private hot tub under the stars, roasting s'mores over an evening fire or an early morning soak in the free standing tub. All of this is located within 20-45 minute scenic drive of hiking trails, wineries, and restaurants . It is our hope that upon your stay you will be reconnected to nature and to the one you came with.

Top guest favorite
A stylish living area features a light-colored leather sofa adorned with dark pillows, complemented by an ornate mirror above. A black coffee table rests on a decorative rug, while two open bookshelves showcase elegant decor. Double French doors lead to an adjoining space.
Home in Waterloo
4.98 out of 5 average rating, 151 reviews

The Ruby/Close to St. Louis and Waterloo Downtown

Welcome to The O'Bannon House in Waterloo, IL, where we offer the best of both worlds! The city limits of St Louis are only about 17 miles away, yet we are located within walking distance of all that the idyllic town of Waterloo offers: great restaurants, shops, and breweries. Enjoy our coffee bar, a fully-equipped kitchen, and a park-like backyard with a fire pit. If you have a larger group, consider booking this unit (The Ruby) and the soon-to-open upstairs unit (The Hugh)!

Top guest favorite
The living area showcases exposed log walls and a warm wooden floor. A stone fireplace serves as a central feature, surrounded by comfortable seating, including floral-patterned chairs. A chandelier provides soft lighting, while a small table and lamp add functional decor adjacent to the fireplace.
Cabin in Imperial
4.97 out of 5 average rating, 368 reviews

Serenity Log Inn - Log Out and Log Inn to Serenity

Welcome to Serenity Log Inn. This authentic 1930s log cabin is located one mile from the historical town of Kimmswick and 25 miles from St. Louis with easy access to major highways. There is a $30.00 fee per use of the historical fireplace. Fee covers set up, dry wood for burning, fire starter and maintenance, and $18.00 fee first use to cover clean up. To prevent infestation of insects, no outside wood allowed. 24 hr notice required.

Top guest favorite
The rock cottage is set amidst trees and autumn foliage, featuring large windows that glow warmly in the evening light. A chimney rises from the side, and natural vines adorn the exterior, blending the structure with its serene surroundings.
Cottage in De Soto
4.97 out of 5 average rating, 136 reviews

Rock House Retreat

Unplug and enjoy a slower pace of life at this picturesque rock cottage. The 1920’s former hunting lodge was built from stone sourced from the property, and is as charming as ever. Enjoy an early morning stroll on one of the many hiking trails, or just relax on the porch while sipping coffee. There are many great hiking opportunities within a short drive, however, once you get settled in you may not find a reason to leave.

Guest favorite
The exterior of a rustic log cabin is shown, featuring a stone chimney and wooden windows. Natural light filters through the trees, casting shadows on the flower beds below. A paved pathway leads to the entrance, framed by a wooden fence.
Cabin in Waterloo
4.91 out of 5 average rating, 148 reviews

Cozy 1953 Countryside Log Cabin Minutes to STL

This one room log cabin was built in 1953 and is located in a safe, friendly Illinois town that is part of St. Louis metro area. You can walk to town (restaurants, craft breweries, concerts, plays) and you're still close to St.Louis attractions. Why fight traffic and worry about parking or safety? Guests love our clean and tranquil cabin and the welcoming town of Waterloo.

Top guest favorite
The exterior of a revitalized building is shown, featuring a white brick facade with black accents. Large windows allow natural light to pour in, while a tree in the foreground adds a touch of greenery. A storefront with the signage 'COLLECTIBLES' is visible at street level.
Loft in Festus
4.96 out of 5 average rating, 130 reviews

The Loft at 12A

An open and updated space with natural light and 10 foot ceilings! This fresh and clean space is conveniently located on a quite corner of Main Street. Walking distance from eateries and cocktail hours. For your convenience The loft is fully equipped with WiFi and A smart station. If you’re in town for business, you’ve found the perfect spot!

Guest favorite
A swing hangs from a sturdy tree, gently swaying in the light breeze. The sun is setting in the background, casting a warm glow over the lush green grass and highlighting the rustic barn in the distance.
Home in Fults
4.94 out of 5 average rating, 234 reviews

Quiet country getaway w/ Hot tub

Welcome to the Homestead Hideaway! Unwind and take in the simplicity of country living. From watching the sunrise to sitting under the stars experience nature with all the amenities. This home comfortably fits 6 people with 3 bedrooms and 2 full bathrooms with plenty of room to enjoy the outdoors.

Popular amenities for Maeystown vacation rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Monroe County
  5. Maeystown