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, 283 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
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, 173 reviews

FUNKS INN-book before 9/15 Save 15% No guest 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 the tiny home is highlighted by a stone façade and a modern roof. A wooden deck features two classic Adirondack chairs, positioned against large glass doors that provide natural light and views of the surrounding grassy area.
Tiny home in Bloomsdale
4.92 out of 5 average rating, 255 reviews

Coeur de la Crème Suite at Baetje Farms

Welcome to the Luxury Tiny Homes at Baetje Farms, where comfort meets countryside. These homes will awaken your senses and enlighten your soul with the cozy, yet spacious intimate feel beneath the stars. Nestled between rolling hills of the Forche du Clos Valley and a spring feed babbling creek the tiny homes are the newest addition to Baetje Farms. Just 3 miles off Interstate-55 at the entrance to wine country, in Bloomsdale, MO, Baetje Farms is the World Renowned Goat Cheese Creamery!

Superhost
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 Fairview Heights
4.86 out of 5 average rating, 140 reviews

Wooded 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 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, 710 reviews

Private Treehouse Retreat | Hot tub

The TreeLoft is the first of two treehouses at BaseCamp—designed for cozy seclusion, romance, and rest. Nestled in a private forest just 1 hour from St. Louis, it blends upscale comfort with immersive nature, while still being 20–35 minutes from hiking, wineries, and dining. ✨Our NEW treehouse, The TreeRise, offers an even more elevated, spacious experience at BaseCamp. Perfect for romantic getaways, anniversaries, personal retreats, and intentional escapes to unplug and reconnect.

Guest favorite
Home in Dittmer
4.96 out of 5 average rating, 626 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 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, 378 reviews

Serenity Log Inn - Log Out and Log Inn to Serenity

Welcome to Serenity Log Inn — a cozy 1930s log cabin nestled among the trees just one mile from historic Kimmswick and about 25 miles from St. Louis, with easy access to major highways. Filled with rustic charm and modern comforts, the cabin is thoughtfully prepared for a relaxing and private stay. The kitchen is stocked with breakfast items to help you settle in and feel at home. Please see "Interaction with guests" section for additional details about the property and your stay

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, 172 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. If you have a larger group, consider booking this unit (The Ruby) and the upstairs unit (The Hugh) so you can all stay in one place!

Guest favorite
The secluded treehouse is elevated among trees, featuring a wooden exterior with a pitched roof. A set of stairs leading to the entrance is visible. Surrounding foliage creates a natural and serene environment, while sunlight filters through the leaves.
Treehouse in Dittmer
4.83 out of 5 average rating, 186 reviews

The Den at Dittmer Hollow

Newly Updated** Enjoy the lovely setting of this romantic spot in nature, with a semi-primitive, modern cozy secluded treehouse in the woods! Explore 10 acres or wind down on the deck before relaxing in the *NEW* hot tub. The cabin inside has a very minimalistic design featuring on the first floor an electric fireplace, air conditioner, table, refrigerator, leather futon couch, kitchenette with a hand crank water pump sink, axe throwing and porta-potty bathroom.

Top guest favorite
The historic log cabin features a traditional wood exterior, accented by a sloped roof and a welcoming front porch. Two rocking chairs and vibrant flower pots are positioned at the entrance, set against a tranquil landscape. Soft lighting enhances the inviting appearance as dusk approaches.
Cabin in Ste. Genevieve
4.97 out of 5 average rating, 230 reviews

Sassafras Creek Cabin

Historic log cabin circa 1840 moved to property June 2020. Take a step back in time with furniture and decor to match the cabin’s time period. Located between two houses in newly formed Ste. Genevieve National Historical Park. It is a 10 minute walk to the main part of downtown and other historic tour sites. Adjoins Early American gift shop called Sassafras Creek Originals which is housed in the circa 1850 Brooks house. Close to wineries, biking and hiking.

Top guest favorite
The house is illuminated softly under the night sky, showcasing its exterior along with an inviting entrance. Surrounding the structure, ground lights create a warm ambiance. Dark trees outline the property, enhancing the sense of a peaceful retreat in nature.
Home in Bloomsdale
5 out of 5 average rating, 81 reviews

Luxury Retreat -Hot Tub, Fire Pit & Private Trails

Goforth Into Nature is a private countryside retreat in southeast Missouri, completed March 2025, designed for a peaceful, secluded getaway. Enjoy a 7-person hot tub, fire pit, and patio under the stars in a quiet natural setting—perfect for a romantic escape or weekend retreat. Inside features a queen pillow-top bed, sleeper sofa, luxury linens, rainfall shower, fully stocked kitchen, washer/dryer, and free Wi-Fi.

Guest favorite
Apartment in Pevely
4.88 out of 5 average rating, 108 reviews

Pevely Getaway Near Festus & I-55 | Free Parking

Experience a peaceful getaway in Pevely, conveniently situated near the Mississippi River, Mastodon State Historic Site, and local parks. With easy access to Festus dining options, outdoor trails, and I-55, this cozy house is perfect for families, extended stays, and contractors. Located just 30 minutes from downtown St. Louis and its major attractions, it provides a serene residential atmosphere.

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