Vacation rentals in Pleasantville

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Top-rated vacation rentals in Pleasantville

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Guest favorite
Home in Lobelville
4.88 out of 5 average rating, 155 reviews

Cozy Pine Log Home

We hand built this 2400 sq.ft home/cabin with local pine logs, these timbers that form the main structure of this cabin are hand notched and stacked local pine. We did most of the work and designing on this and were able to put a personal touch to the work inside and out. NOTE!!!This is a rustic place with modern convenience, (Knotty hickory cabinets, Pebble and tile showers, Bamboo floors, Local, pine, log exterior walls, Tulip popular interior, Log and barn wood furniture. We welcome you.

Guest favorite
The main room features a dining table with seating for six and a cozy sofa against the wall. A refrigerator is positioned in the corner, and natural light filters through window curtains, enhancing the light-colored walls and flooring.
Guesthouse in Pleasantville
4.95 out of 5 average rating, 132 reviews

Guest House on Beautiful Cane Creek

Comfortable Guest House on our 32-acre family farm located next to a picturesque Amish area. Nearby parks and access to recreational activities along the Tennessee River -- hiking, swimming, fishing, canoeing and kayaking. Loretta Lynne's Restaurant/Event Park - 30min. Kitchen for guests to prepare meals and snacks. Guests are welcome to tour the farm. Only one guest group (individual, couple or small group) occupies the Guest House building at any one time, so complete privacy during your stay.

Top guest favorite
The entrance to Wee Nook is framed by lush greenery, with a curved roof and a wooden door. A stone pathway leads to a pavilion, offering outdoor seating among the surrounding trees. The natural setting provides a peaceful ambiance in the woods.
Earthen home in McEwen
4.99 out of 5 average rating, 1,008 reviews

Wee Nook- a Hobbit Hole

Wee Nook is a 360 square foot living space with a full kitchen and bathroom. It is tucked underground in the middle of the woods. Please come enjoy the woods, farm animals, trails, pond and wide open space while you're here! As JRR Tolkien said: “In a hole in the ground there lived a hobbit. Not a nasty, dirty, wet hole, filled with the ends of worms and an oozy smell, nor yet a dry, bare, sandy hole with nothing in it to sit down on or to eat: it was a hobbit-hold, and that means comfort.”

Top guest favorite
A charming cabin is framed by lush greenery and towering trees, featuring a rustic wooden facade and a blue metal roof. The entrance is marked by a simple door surrounded by vibrant bushes and plants, set against a backdrop of soft, sunlit grass.
Cabin in Fairview
4.97 out of 5 average rating, 191 reviews

Whispering Waters Cabin by the Creek

Whispering Waters offers a quiet space to relax and enjoy your time spent away from home. It is a four room cabin adjacent to Caney Fork Creek, which feeds into the South Harpeth River in Fernvale. The cabin easily hosts four guests. The queen size bed is complimented by a sleeper sofa in the living room, which sleeps two as well. It's an intimate space located in a lovely setting. IF you are booking "same day" please give me a call so I can make any necessary last minute arrangements.

Top guest favorite
Cabin in Centerville
4.96 out of 5 average rating, 428 reviews

#1 Peaceful Hills Retreat Lodge 97 Acres Creek

Peaceful Hills Lodge is the perfect place to relax on the front porch while enjoying the fresh air, the sounds of nature, and a pond. Inside is a large stone fireplace, a spiral staircase & a jacuzzi bathtub. Located on 97 acres in a gorgeous location with a spring-fed creek, swimming hole, rope swing, hammock & fire pit. You'll find the spring fed stream is on a private lane that brings you into Peaceful Hills! The Lodge, Cabin & Cottage is where you’ll definitely enjoy some peace & quiet!

Top guest favorite
The exterior of a charming white house is framed by lush green trees. A welcoming front porch is highlighted by decorative railings and lantern-style lights. Subtle architectural details reflect the historical character, while a manicured lawn leads to the front steps.
Home in Columbia
5 out of 5 average rating, 213 reviews

Historic Biddle Place Downtown Columbia

Biddle Place is an elegant little home conveniently located a few minutes walk from the town square. Situated on the front lawn of Historic Rally Hill Manor, you're ensured a lovely backdrop to your stay. The Mulehouse, an intimate music venue, is just across the street. Biddle Place is perfect for enjoying time on the front porch, nestling in, or heading downtown where you'll find antiques, quaint shops, bookstores, great food, craft beer, wine tastings, stout coffee and good conversation.

Top guest favorite
A cozy bedroom is revealed through an open door, showcasing a spacious bed dressed in plaid and striped bedding. A ceiling fan provides subtle airflow, and a bench sits at the foot of the bed, enhancing the room's rustic charm.
Cottage in Centerville
4.97 out of 5 average rating, 172 reviews

River Run Cottage at Horseshoe Bend Farm

Welcome to River Run Cottage! Our 280 acre farm has views of the beautiful Duck River Valley & has 3 mi. of private river frontage. The cottage is located adjacent to our winery tasting room, open Thurs. - Sunday. (Horseshoe Bend Farm Wines) We also grow blueberries and offer picking opportunities for a real farm experience. Canoeing/Kayaking, Fishing, Hunting, Horseback Riding, ATV and Hiking experiences located nearby. Near I40, Loretta Lynn’s Ranch and 1 hr. to Nashville.

Guest favorite
A single-story modular home is presented with a covered front porch featuring a wooden railing. Blue window shutters complement the light exterior. A grassy area surrounds the house, with a pathway leading to the entrance. The setting conveys a peaceful rural environment.
Farm stay in Waynesboro
4.88 out of 5 average rating, 113 reviews

Storybook Farm Tennessee, Guest House

Stay at our quiet, safe, and private horse facility/mini farm. Ponies to draft size horses call it home. Various other farm animals live here. The guest house is a three bedroom modular home with two baths. You have the house to yourself. There is a carport not included and is used for storing horse drawn equipment. Beyond the pasture to the east is a wooded area with a trail that borders the Green River. The farm is 9 miles from the Buffalo River. It is 2 miles to town.

Top guest favorite
Cabin in Savannah
4.99 out of 5 average rating, 119 reviews

New! Coral Ridge on Indian Creek-A Couples Getaway

Coral Ridge is the perfect place for two. Escape it all and enjoy nature and relaxation at it’s finest. Take in the amazing view while soaking in a hot tub and listening to the sounds of the waterfall all at the same time. Need a little adventure? Take a hike down our scenic trail to the beautiful clear waters of Indian Creek. Wade in the rapids, cast for a small mouth, or just simply kick back and meditate in these beautiful surroundings.

Top guest favorite
The exterior of a charming white house is highlighted by a green metal roof, complemented by a brick chimney. Florals hang from hooks on the porch, which features a welcoming entrance. The surrounding greenery offers a serene country setting.
Home in Parsons
4.99 out of 5 average rating, 162 reviews

Little House on Main

Located just 1.5 hours from Nashville and 6 miles from the Tennessee River, this cozy 80-year-old home is a perfect weekend escape. Nestled between two Tennessee State Parks, it’s ideal for hiking, fishing, and unplugging from the city. We renovated it as newlyweds, keeping its charm and quirks. Whether you're looking for a romantic retreat or a quiet reset, come enjoy small-town living at its best—we hope you love it as much as we do.

Top guest favorite
A spacious country home is set among lush green trees, with well-maintained grass surrounding the property. The blue sky provides a bright backdrop, while large windows reflect natural light. The inviting entrance features a pathway leading to the house.
Guest suite in Dickson
4.98 out of 5 average rating, 185 reviews

Country Penthouse

Skip the same old hotel experience and escape the Country Penthouse. The Country Penthouse is set in the beautiful Tennessee countryside amongst the trees. Watch as the sunrises over the tree tops from the private deck and the sunset from the private balcony. Hear the sounds of nature and the birds singing. Let time slip away as you relax and unwind. Enjoy the the wide open spaces away from the hustle and bustle of the city.

Top guest favorite
A charming cabin is shown, featuring a screened porch that connects to a wooden deck. The exterior is painted in soft gray with red shutters, complemented by vibrant landscaping including various flowers. The metal roof adds a rustic touch to the overall appearance.
Cabin in Hurricane Mills
4.99 out of 5 average rating, 107 reviews

Lillie's Pad

Lillies Pad sits on a 30 acer farm. If you like your privacy then this is for you. The cabin has a screened porch that lets you enjoy the view of Duck River. A lighted pavilion with a firepit is also on site for hanging out, which is even closer to the river. Surrounding properties are large farms, private hunting properties, lodges. It is country living, peaceful, a perfect get-a-way

Popular amenities for Pleasantville vacation rentals