Holiday houses in Pleasant Shade

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Top-rated holiday rentals in Pleasant Shade

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

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Top Guest favourite
Treehouse in Franklin
4.99 out of 5 average rating, 154 reviews

Treetop Views *Trails, Fishing *No Cleaning Fee

Amazing two-story house nestled high up in the trees. A true treehouse! This treehouse sits amongst a forest of poplar trees and feels very secluded and private. It has spectacular views of Kentucky’s rolling hills as it looks out across the valley. This treehouse was hand built and handcrafted with love and attention to detail. Located just off of I65 outside the historical little town of Franklin, KY. We are located between Nashville (45min), Bowling Green (35min) and Mammoth Cave (55 min).

Top Guest favourite
A comfortable living area features a cozy sofa with textured cushions and a warm throw blanket. A wooden coffee table centers the space, complemented by decorative items. Natural light fills the room through a large window, and a small bookshelf stands against the wall.
Home in Lebanon
4.97 out of 5 average rating, 118 reviews

Cozy Home with No Cleaning Fee in heart of Lebanon

You will never be far from all that Lebanon has to offer staying in this cozy two bedroom home. Located just 1.4 miles from Lebanon Town Square, 1 mile from Cumberland University and 3 miles from the Wilson County Fairgrounds you are just minutes from everything you need. And if you are looking for the sights and sounds of Nashville you are a quick 30 minute drive. This fully remodeled home has all new appliances, comfortable beds and a fun retro bathroom. Come enjoy this peaceful getaway.

Top Guest favourite
A cozy living area is highlighted by wooden walls and natural light. A dining table with chairs occupies one side, while a comfortable leather sofa with accent pillows faces a decorative fireplace. A chandelier hangs above, emphasizing the inviting ambiance.
Cabin in Moss
4.98 out of 5 average rating, 428 reviews

Tennessee Retreat Log Cabin Near Dale Hollow Lake

Tennessee Retreat Log Cabin, nestled in the hills of the Eastern Highland Rim, has everything you need to escape in style. Amenities (like WiFi and Cable TV) let you enjoy the serenity of the woods with casual or formal dining, antique or necessity shopping, water activities on Dale Hollow Lake - a 15 minute drive, wineries, historic & natural attractions & live entertainment. Perfect for business or pleasure trips, extended stay or hosting weddings or events on the extensive lawn. Welcome!

Superhost
A charming tiny house is nestled among trees, featuring a cozy deck with an umbrella for shade. Red and orange pumpkins rest near the entrance, and a small grill is positioned beside a comfortable lounge chair. The surrounding area is adorned with natural soft grass and gravel.
Tiny home in Lebanon
4.84 out of 5 average rating, 1,020 reviews

The Limerence Tiny House - The Legend!

Twig City Farm's famous Limerence tiny house by the Impossible Forrest! Visit for a one of a kind, unique fun life experience! Kitchenette, TV, wifi, REAL plumbing! Deck, grill & fire pit! Primitive trails! Close to lakes, country music stars, restaurants & shoppes & just 30 miles to downtown Nashville! Arrive anytime after 3 pm. Includes Country breakfast at Starstruck Farm 7 to 11 am! Starstruck Farm is 3 miles north on Highway 109. Lots of sightseeing and photo opps there also!

Top Guest favourite
A tranquil sunset is reflected on the calm surface of the Cumberland River, with vibrant shades of orange, pink, and purple filling the sky. Silhouettes of trees frame the scene, contrasting against the colorful backdrop.
Guesthouse in Granville
4.96 out of 5 average rating, 129 reviews

The Hoot Camp, A Granville Home with a View

The Hoot Camp in located in historic Granville, TN, situated just a mile from the town center and only two miles from Wildwood Resort and Marina. There are plenty of things to do during your stay, including antiquing, wine tasting, hiking and water sports. With large decks and a hot tub for relaxing, the Hoot Camp is ideal for rejuvenating your soul and enjoying sweeping views of the Cumberland River. Two restaurants, music and additional water activities nearby. Come and Enjoy!

Superhost
The cottage features a vibrant red metal roof and a welcoming porch with wooden chairs. A view of the surrounding area showcases greenery and buildings in the distance, including a clock tower, highlighting the cottage's proximity to the town center.
Cottage in Gainesboro
4.93 out of 5 average rating, 305 reviews

A vintage cottage in historic downtown Gainesboro

The Cottage is a private space conveniently located one block from the Gainesboro square in picturesque Jackson county. Close by are many outdoor activities such as fishing the Cumberland River or canoeing/kayaking on the Roaring River, where there is a boat ramp, a swim area & playground. Just 12 miles to Cummins Falls State Park & 25 minutes to Cookeville. If you’re a history buff, make sure to visit the incredible Jackson County Archives & Veterans Hall at 104 Short St.

Top Guest favourite
Loft in Watertown
4.98 out of 5 average rating, 127 reviews

The Cedar Loft

The Cedar Loft is a beautiful space in the country nestled on 40 acres with a fantastic view. Conveniently close to I-40 with a driving time of 35 min. to the Nashville airport or 45 min. downtown Nashville. This brand new above garage loft has a private entrance. Kitchen offers granite counters, fridge, microwave, oven, and dishwasher. For laundry there is a washer/dryer combo. We offer wifi, have good cellular reception and offer an assortment of DVDs and board games.

Top Guest favourite
An open living area features exposed brick walls and wooden rafters, complemented by contemporary furniture. A round dining table with four light blue chairs sits on a patterned rug, near a fully equipped kitchen with wooden cabinetry and modern appliances. Natural light streams through large windows.
Loft in Carthage
4.99 out of 5 average rating, 105 reviews

Cozy in Carthage

Come stay at this beautiful and luxurious loft apartment overlooking historic downtown Carthage Tennessee. Downtown Carthage with an amazing view of the Cumberland River offers a small town variety of restaurants and retail stores. Whether one enjoys the sounds of historic church bells ringing or the convenience of a bar within walking distance, the quiet friendly small town charm is sure to rub off on you. Large retail stores are within 2 miles of downtown Carthage.

Top Guest favourite
A serene country road is flanked by vibrant autumn trees showcasing orange and gold leaves. A quaint cottage with a green roof is partially visible, nestled among the foliage and softly illuminated by natural light.
Cottage in Hickman
4.95 out of 5 average rating, 798 reviews

Gibbs Farm Cottage; Kids and Pets Welcome

Our motto is: Clean, convenient, comfortable and affordable. High speed fiber optic Internet/WIFI. Pet/kid friendly. Plenty of parking, five miles off I-40. Located on a 68-acre working farm, the cottage sits in a peaceful valley surrounded by rolling hills, pastures and woods. Relax and enjoy the tranquility of the country. Get a taste of farm life. Or enjoy outdoor activities available in the area. Come enjoy our little piece of heaven!

Top Guest favourite
The exterior of a single-story house is shown, featuring a stone façade with wood accents. A metal roof caps the structure, and large windows allow natural light to enter. A stone pathway leads to the front door, which is framed by landscaped grass and decorative shrubs.
Home in Cookeville
5 out of 5 average rating, 208 reviews

Sheep’s Meadow Cottage

1 king bed, 1 queen fold-out couch, dedicated workspace. Take it easy at this tranquil and cozy getaway surrounded by a sheep meadow, just 2 miles from I-40. Fishing pond available upon request. We are located just 15 minutes from the charming small town of Cookeville, TN. We are also near beautiful natural attractions, such as waterfalls and lakes. Cookeville is centrally located between Nashville, Knoxville, and Chattanooga.

Top Guest favourite
A cozy living area features a dark gray sofa with bright yellow accents and a coffee table adorned with greenery. A flat-screen television is mounted on the wall opposite the sofa. Doorways lead to additional rooms, enhancing the space's openness.
Cottage in Carthage
4.98 out of 5 average rating, 306 reviews

The Farmhouse...One Mile from Caney Fork Boat Ramp

Welcome to the Farm House!! This beautifully updated 1BD/1BA cottage is located approximately one mile from the Caney Fork boat ramp in Gordonsville and 10 minutes from Interstate I-40. Surrounded by acres of mature trees, foliage, and the sounds of the Caney Fork River, you will relax in the epitome of country living. PLEASE NOTE: Uber and Lyft services are NOT available in the area. Please plan accordingly.

Guest favourite
A cozy tiny cabin is set amid a gravel area, surrounded by trees. A hammock is gently draped between posts, while wooden chairs are placed nearby. The cabin features a porch with a railing and string lights, extending a welcoming atmosphere.
Tiny home in Celina
4.97 out of 5 average rating, 115 reviews

Sunset Ridge Cabin- Snow Hill Farm

Our cozy tiny cabin is the perfect get away for your vacation. Come relax just 10 minutes from beautiful Dale Hollow Lake in our peaceful location here in Celina, TN. Our goal is to allow you to unwind and put a pause on the craziness of everyday life. Enjoy your cup of coffee with a view of our rolling hills pasture and farm animals. *All natural cleaning supplies used. Yay for a chemical free vacation!*

Popular amenities for Pleasant Shade holiday rentals

  1. Airbnb
  2. United States
  3. Tennessee
  4. Smith County
  5. Pleasant Shade