Holiday rentals in Greenville

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Top-rated holiday rentals in Greenville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A beautifully restored stone castle sits amidst a backdrop of autumn foliage. The structure features tall windows and a distinctive tower, with greenery surrounding the gently sloping lawn that leads to a set of stone steps.
Castle in Ironton
4.99 out of 5 average rating, 94 reviews

Historic Goulding Castle circa 1846

***Please do not send any messages asking about weddings or events*** Amazingly restored Castle built by TR Goulding in the 1800’s. This unique and majestic property sits on 9 acres of Shepherd Mountain and connects to over 600 acres of hiking and biking trails on Shepherd Mountain. Enjoy beautiful views and a forest setting while still being minutes from restaurants and town. The property boasts priceless statuary, a rebuilt grotto, beautiful interior and the most peaceful grounds to enjoy.

Superhost
A 20-foot yurt is situated among bare trees, surrounded by nature. A spacious wrap-around deck enhances outdoor living. The structure features a circular design with a clear dome top and a single door visible. Nearby, a separate area can be seen, possibly for cooking or relaxation.
Yurt in Fredericktown
4.85 out of 5 average rating, 128 reviews

St Francis River: The Blue Yurt and Hot Tub

Let your adventure begin inside the tranquil experience of this 20 ft yurt. Don't let the space fool you, the uniquely curved walls give ample space for a romantic getaway or a relaxing time with friends. The clear dome top provides a magical viewing experience from the queen size bed. The yurt is nestled in the heart of the Ozark Mountains. The expansive, romantically lighted, wrap-around deck provides a panoramic view of the St. Francis River where you can immerse yourself in the hot tub.

Superhost
The exterior of a rustic grain bin house is showcased, featuring a stone and wood entryway with a covered porch. A grill is positioned nearby on a gravel patio, while trees are visible in the background, providing a natural setting.
Dome in Piedmont
4.73 out of 5 average rating, 45 reviews

The Grain Bin in Piedmont-Clearwater Lake-King Bed

Feel refreshed when you stay in this rustic gem a very unique grain bin! Great location-Just a few minutes from Clearwater Lake, Black River, St. Francis River, Sam A Baker, Lon Sanders Canyon. Walking distance to flea market. Only 1/2 mile to Pine-Hill drive in, 1 mile to Dollar General & close to several good restaurants. 3 sleeping areas , 2 baths and is fully stocked. Has great high speed wi-fi. Cook dinners in the kitchen, BBQ on the grill, watch tv or hang out on the porch or deck!

Top guest favourite
Treehouse in Greenville
5.0 out of 5 average rating, 380 reviews

Treehouse Escape• Secluded•HOT TUB year around

"The Roost" is a modern treehouse 2 hrs south of St Louis near Wappapello Lake. Yes it has indoor plumbing & running water. Accommodates two adults, has a fully equipped kitchen, and breakfast items are provided for you to cook. Surrounded by thousands of acres of national forest. Observe wildlife sightings from the deck while soaking in the private hot tub, sleep comfortably in a queen size pillowtop Serta bed on a Motion Air base, and relax as you enjoy the ambience of the fireplace.

Top guest favourite
Treehouse in Perryville
4.95 out of 5 average rating, 208 reviews

Rustic reTREEt Treehouse Getaway

This treehouse features a gorgeous floor-to-ceiling stone indoor/outdoor fireplace, vaulted ceiling, and many large windows which provide natural light and beautiful views. The interior design fuses natural elements of wood and stone, with a more refined and polished urban country look. A partition wall creates intimate spaces w/in this large (950 sq.ft.) open floor plan. Highlights: king size bed, corner claw tub, rainfall shower, reading area, 65" TV, large deck,BBQ grill and WIFI.

Top guest favourite
A modern cabin exterior is framed by a vibrant landscape. Light-colored siding is contrasted with a dark roof, and the entrance features a welcoming porch supported by wooden beams. Potted flowers add a touch of color, while windows allow natural light to fill the interior.
Cabin in Piedmont
5.0 out of 5 average rating, 80 reviews

By Clearwater Lake/Black River-Golf Range On-Site

One bedroom cabin loaded with amenities! Private location in a 12 acre field with wildlife to watch and also conveniently located a few blocks from Main Street. NO EXTRA FEES ADDED/no household chores! Free parking, plenty for boats and atv’s also No amenities left out-laundry facilities, all cooking supplies, stocked coffee bar, high speed internet, Netflix, plush king bed, rainfall shower head and more. Please note: a silicone heat pad is provided for all irons in the bathroom.

Top guest favourite
Tiny home in Patterson
4.94 out of 5 average rating, 34 reviews

Rustic Tiny Home

Get away from it all when you stay under the stars. This sweet little accommodation is rustic on the inside and nestled in the Missouri Southeast close to the historic Sam A. Baker State Park. Two full hook up RV sites are on either side of the tiny home, allowing for camping of family or friends. Your host is close by in a home next door allowing us to quickly meet needs that may surface during your stay. The unit does have a washer/dryer as well. Note: RV rental is separate.

Guest favourite
A covered porch offers expansive views of rolling hills and a glistening pond. A swing chair is positioned to the side, inviting relaxation, while flower beds with vibrant blooms border the entrance. Sunlight illuminates the landscape, enhancing the natural beauty of the surroundings.
Cabin in Fredericktown
4.96 out of 5 average rating, 346 reviews

Cabin on the farm

The Space Rustic charm meets the serene beauty of the Ozarks in this magical setting overlooking our farm, offering a perfect retreat for rest or a base camp for your next adventure. Inside, you'll find a cozy living space decorated with modern farmhouse charm, complete with a warm electric fireplace. Relax in the comfortable king-size bedroom after a day of exploring. The cottage also includes a well-appointed bathroom and a functional kitchenette for your convenience.

Top guest favourite
Cabin in Williamsville
4.97 out of 5 average rating, 118 reviews

Cypress Bend cabin w/hot tub on Black River

Cozy new built cabin on a bend of the beautiful Black River. You’ll walk up the 14 stairs to a large screened in covered deck with hot tub and sitting area, and gas grill. The glass doors and windows allow you views of the river. The theme throughout is Indian-Aztec. Accommodates only two adults. If you’re looking for a peaceful/romantic get away this is the perfect place. Located approximately 2 hours south of St. Louis, and less than 15 minutes from Poplar Bluff, MO.

Guest favourite
The cabin exterior showcases a unique combination of stone and siding with a gently sloped roof. A small wooden deck leads to the front door, while a gravel driveway offers ample parking space. Surrounding trees provide a natural backdrop.
Cottage in Wappapello
4.92 out of 5 average rating, 62 reviews

Ridge Road Casita

Welcome to Ridge Road Casita near beautiful Wappapello Lake. Take time to unwind and enjoy the lake life and all it has to offer in our one bedroom, quaint and cozy cabin. Within minutes from Peoples Creek and Sundowner Marina. We have plenty of space to park a boat and vehicle. The Camp is approximately 8 miles away, if you’re in the area to catch a live band. There is a Dollar General close by and a variety of restaurants within the Wappapello area to enjoy!

Superhost
A charming cabin sits amid lush greenery, featuring a welcoming front porch with seating. The quaint exterior is complemented by muted earth tones, and colorful elements enhance its character. The sky transitions from blue to soft pink at sunset, adding a serene backdrop.
Cabin in Williamsville
4.87 out of 5 average rating, 127 reviews

Keener Springs Springhouse

The Spring House at Keener Spring sits on a bluff overlooking beautiful Black River in the Ozark Foothills. Keener Spring is one of the largest privately owned springs in the country emitting 14 million gallons per day. The spring and the unique, water filled Keener Cave are the focal points of the 65 acre property. There are numerous places including our gravel bar within walking distance to BBQ, picnic, or just relax in the sunshine with your favorite beverage.

Superhost
A cozy cabin is set amidst natural surroundings, showcasing a hot tub on a wooden deck. A gravel pathway leads to the entrance, lined with soft lighting and surrounded by trees, enhancing the secluded ambiance of the private property near the lake.
Home in Lost Creek
4.84 out of 5 average rating, 129 reviews

Camp Bluegill Lake House

New, modern, and cozy with tons of amenities and activities. Relax in the hot tub overlooking the private lake or lounge on the private beach and watch the kids have fun in the paddle boat. Beautiful, secluded property on 5 acres. Tons of parking and easy in and out access for trailers and covered parking. Minutes from beaches, boat ramps and marinas on beautiful Lake Wappapello. Multiple state parks, trails and recreational activities also within minutes.

Popular amenities for Greenville holiday rentals