Holiday rentals in Maeystown

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Top-rated holiday rentals in Maeystown

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Guest favourite
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, 244 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!

Guest favourite
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
4.95 out of 5 average rating, 187 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 favourite
A cozy living area features grey walls and stylish furnishings, including a dark leather sofa and a matching armchair. A geometric area rug adds subtle color underfoot. Natural light shines through the window, and a piece of wall art adds character to the space.
Flat in Benton Park Historic
4.97 out of 5 average rating, 239 reviews

Cozy 1BR Apartment the "Ferner Flatette"

This unique, minimalistic apartment is located in the historic Benton Park neighborhood. A stroll away from restaurants, coffee shops, antique row and the park complete with lakes and walking paths. Recently renovated, its just minutes from downtown attractions: the Gateway Arch, Busch Stadium, Enterprise Center and Union Station Aquarium. Strict capacity of 2 persons. Window unit A/C, central heat. No pets, no smoking, no local guests. Government issued photo ID required prior to checkin.

Guest favourite
The modern home features a spacious wooden deck with steps leading to a well-maintained garden. Large glass doors dominate the front facade, allowing natural light to flood the interior. Lush trees provide a serene backdrop, complementing the inviting outdoor space.
Home in Caseyville
4.91 out of 5 average rating, 102 reviews

Relaxing Oasis with Free Bottle of wine+brkfst

Enjoy serenity and tranquility at our modern home tucked away in a private setting just 5 short minutes from Downtown St Louis. Complementary bottled water, continental breakfast(packaged muffins) and a bottle wine will pamper you the moment you arrive.Unwind in our luxurious multifunction shower+memory foam mattress Test your swing on our scenic driving mat or unwind around the crackling outdoor fire pit. Spa and Special Occassion add-on packages available. Private off street parking.

Top guest favourite
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, 162 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 favourite
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, 554 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 favourite
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 favourite
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, 149 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)!

Superhost
A serene view of a micro cabin is presented against a vibrant sunset sky, displaying shades of orange and pink. The cabin is illuminated softly from within, surrounded by trees and a grassy area leading to a rustic fence.
Farm stay in Hillsboro
4.92 out of 5 average rating, 194 reviews

Shagbark Hickory Cottage (Hot tub & Sauna)

Take it easy at this unique and tranquil getaway. Enjoy a detox in our handcrafted sauna, or take a soak in the hot tub under the stars! Full kitchen, bathR w/claw foot, & screened in porch. It’s very private, with land to explore. Take a stroll to the pond or creek where you will see a little piece of history, or possibly enjoy a visit from our sweet cows. Close to La Chance winery, Desoto town, Big River access points, valley view glades, & Washington state park.

Top guest favourite
A charming brick cottage is situated along a brick-lined street, adorned with vibrant greenery and flowering plants. The entrance features a light green door framed by lush plants, while large windows provide a glimpse of the inviting interior.
Cottage in Belleville
4.96 out of 5 average rating, 527 reviews

The Historic Garfield Inn

Welcome to the Garfield Inn. A cozy cottage off a brick-lined street in an historic Belleville neighborhood. Coffee, tea, hot cider and chocolate are provided. We are in walking distance to downtown Belleville, and free parking is available. The neighborhood is quiet and peaceful. There is a barbeque grill, covered back patio, gazebo and lovely gardens. Small well-behaved dogs are welcome. Enjoy your privacy The light is always on. We can't wait to see you.

Top guest favourite
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, 134 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 favourite
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 holiday rentals

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