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Vacation rentals in Pleasantville

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Top-rated vacation rentals in Pleasantville

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

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Top guest favorite
Cottage in Centerville
4.98 out of 5 average rating, 363 reviews

#1 Peaceful Hills Retreat Cottage, 97 Acres, Creek

Peaceful Hills Cottage is the perfect place for you to find some peace & quiet. The cottage is located in a gorgeous location with a spring-fed creek, swimming hole, big yard, hammock & fire pit. If you enjoy being surrounded by nature like birds, deer, turkey and the bright, twinkling stars, while staying in a clean, comfortable home, then look no further! Peaceful Hills Cottage is the perfect place where you will definitely find some peace and quiet in the beautiful rolling hills of Tennessee!

Top guest favorite
Cabin in Linden
5 out of 5 average rating, 11 reviews

Cozy Cardoness Cabin on Private Lake w/ Waterfall!

Enjoy days of tranquility and fun at this cozy and newly built guest cabin set deep in the woods on a private lake! Here you will experience a park-like setting surrounded by nature while still having all the amenities of modern life including high speed internet, smart tv, full kitchen, washer/dryer, and central ac. From the deck of your cabin you will have a bird's eye view of a beautiful lake with ducks and hear the continuous water sounds of a waterfall and fountain which lights up at night.

Top guest favorite
Home in Hohenwald
5 out of 5 average rating, 13 reviews

The Baker House

Welcome to The Baker House, a fully renovated 1940s gem in the heart of Hohenwald, Tennessee. This cozy two-bedroom, one-bath home is ideal for couples, small families, or travelers exploring the area. All essentials provided (fully equipped kitchen, linens, towels, toiletries, etc.) Walking distance to downtown and the Elephant Discovery Center and unique local shops and eateries. Walmart only 1.5 miles away. Close to Natchez Trace Parkway and the brand-new Devil's Backbone State Park. No pets

Guest favorite
Home in Lobelville
4.89 out of 5 average rating, 177 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.

Top 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
4.96 out of 5 average rating, 141 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
A cozy living area features a sectional sofa with plump cushions, complemented by a comfortable chaise. A round dining table is visible nearby, beneath a modern chandelier. Artwork depicting guitars adorns the wall, while a potted plant adds a touch of greenery to the space.
Apartment in Holladay
4.98 out of 5 average rating, 109 reviews

Holiday In Holladay at “The Station”

Take a holiday in Holladay! Relax at this unique and tranquil getaway in the heart of Holladay, TN! Located 5 minutes off Exit 126 on Interstate 40, this cozy apartmen is only minutes from the TN River, Birdsong Marina, Nathan Bedford Forrest, and Natchez Trace State Park. This area is a known as Sportsman's paradise, and this property is designed with that in mind, with barnwood accents and a beautiful, large cedar countertop. There's a queen bed and a pull out sofa for kids or extra guests.

Guest favorite
A contemporary cabin features a sleek black exterior with two large windows. A spacious wooden deck surrounds the cabin, showcasing warm-toned wooden railings. A grill is situated on the deck, and trees provide a natural backdrop, enhancing the sense of seclusion.
Cabin in Lobelville
4.9 out of 5 average rating, 97 reviews

Black Betty on the Buffalo

Black Betty is located right beside the river at the halfway point on the kayaking route from the Buffalo River Resort. This is a perfect place to enjoy a few peaceful days by the water :) *2 wineries within 25 mins (Horseshoe Bend Farm + Grinder’s Switch) *Loretta Lynn’s 10 mins away *Walmart 30 mins away *Amish store 5 mins away *Log Cabin Restaurant 10 mins away *RZR/4wheeler riding *Buffalo River Resort 5 mins away *fresh fruit/produce 5 mins away *no Wi-Fi yet, on waiting list. Soon :)

Guest favorite
A dining area features a compact wooden table surrounded by four white chairs. A contemporary pendant light hangs overhead, illuminating a vase of greenery. A coffee maker and artwork add to the aesthetic, while a green cabinet serves as a functional accent.
Home in Hohenwald
4.9 out of 5 average rating, 84 reviews

Harper's Haven

This newly renovated property was carefully curated and thoughtfully decorated, featuring midcentury modern flares. Here we will offer a comfortable two-bedroom, one bath manufactured home that will exceed all your expectations. We make it our goal to give our guests a pleasant and memorable getaway. Whether you're looking for a weekend retreat or an extended stay, this will be the perfect spot for you! We are located about 4 miles from the Natchez Trace Parkway, and about 2 miles from town!

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
4.98 out of 5 average rating, 1,046 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
Cabin in Lobelville
5 out of 5 average rating, 33 reviews

Hilltop Retreat w/ Wood Fire Hot Tub & Stargazing

Between the Pines is the ideal off-grid retreat for nature lovers seeking to unwind in a cozy cabin where trees frame every window. Located 75 minutes west of Nashville, it’s the perfect place to unplug and reconnect with your loved ones. Surrounded by wooded hills free from light pollution, you’ll have a front-row seat to the stars. Whether you’re soaking in the wood-fired hot tub or roasting marshmallows by the fire, every detail of our cabin was built with your relaxation in mind.

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, 188 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.

Top guest favorite
Cabin in Savannah
4.99 out of 5 average rating, 142 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.

Popular amenities for Pleasantville vacation rentals