Vacation rentals in Oakridge

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Top-rated vacation rentals in Oakridge

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

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Top guest favorite
A charming tiny house is nestled among lush trees, featuring a welcoming front porch with seating. Large windows allow natural light to flood the interior space, while a covered area provides shelter for enjoying the outdoors. The exterior is complemented by a simple, unobtrusive color palette.
Tiny home in Pegram
4.98 out of 5 average rating, 437 reviews

Little House in the Woods

This oasis in the trees is waiting to help you escape, renew and rejuvenate! Located on over thirteen acres of beautiful woods, bordered by a spring-fed creek, it’s a great place to stay in or get out and explore. We love to offer our guests not only a great place to stay but an experience they will talk about for years to come. We love providing lots of little extras to help make your time here really special. This is the perfect spot for a romantic getaway, family fun vacation, or solo retreat

Top guest favorite
The charming cottage entrance features a welcoming porch with a ceiling fan and soft lighting. Stairs lead up to the door, surrounded by neatly trimmed greenery and potted plants. An American flag is displayed on one side, enhancing the inviting ambiance.
Tiny home in Dover
5 out of 5 average rating, 106 reviews

Tiny Home, river view, boat parking, & hot tub.

Welcome to Cottage on the Cumberland – where nature's embrace meets modern comfort! You can disconnect from and find yourself in an unforgettable lakefront experience. With LBL, KY Lake, Lake Barkley, & Ft. Donelson minutes away, you're in the heart of recreational paradise. So, whether it's fishing, hunting, boating, ATV’s, horseback riding, hiking, or just enjoying the beauty of nature, come & experience tranquility & adventure all together! Please read hot tub info in “Other Details to Note”.

Guest favorite
A charming treehouse is elevated among tall trees, surrounded by lush greenery. The wooden structure features large windows offering views of the forest, and a spacious deck extends outward for outdoor enjoyment.
Treehouse in Pegram
4.91 out of 5 average rating, 344 reviews

Private Treehouse Escape Minutes from Downtown

Connect with nature at this unforgettable escape in Nashville's backyard. This treehouse is nestled in a Tennessee hardwood forest in a hollow. Close to the city, but away from it all, it's a perfect place to retreat from normal life. This isn't a tree fort. It's a tiny house with a loft in the trees over a trickling spring fed creek. It's private with all windows facing the forest. All the fun of being a kid w/ comforts of home like toilet, ac, electric fireplace, heater & 3 season hot shower.

Top guest favorite
Cabin in Dover
4.98 out of 5 average rating, 261 reviews

Cabin on Scenic Farm

Hunt House Cabin: Dogwood Springs Farm & Cabins. If you are visiting Stewart County, this 3-bedroom barndominium is immaculate and truly affordable. It sets on top of one the highest peaks in county with a spring-fed pond at the bottom of the hill with hiking trails. Enjoy the fireplace, fire pit & spacious patio. No cameras. Relax & watch the horses! Boat parking is available. Only 2 miles to boat dock. 1-mile to Cross Creeks. We’ve added a scavenger hunt to make the experience adventurous.

Top guest favorite
A tranquil sunset sky is displayed with colorful clouds in shades of pink and blue. The tiny house is seen on the right, featuring a porch and a small wooden privacy screen. The surrounding area is lush with green trees and an expansive grassy space.
Home in Southside
4.99 out of 5 average rating, 124 reviews

Paradise Hill Tiny House

Relax in this calm, stylish space. Come enjoy your stay at our small, quaint, inviting tiny house located in a peaceful country setting. Property is very close to the Historic Southside Market, Historic Collinsville and a short drive to beautiful Charlotte, TN where you can shop their unique variety of farm to table and craft stores. Only 14 miles to Clarksville, TN, 26 miles to Dickson, TN and 42 miles to Nashville! Come relax in the country and soak in the beauty and peacefulness of it all!

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, 1,020 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 cozy cabin is nestled among lush greenery, partially obscured by mature trees. A gravel path leads to the entrance, which is flanked by wooden accents. A small outdoor seating area is visible, enhancing the connection to the serene natural surroundings.
Cabin in Chapmansboro
4.96 out of 5 average rating, 406 reviews

White Duck

Keep it simple at this peaceful and centrally-located cabin minutes from Interstate 24. Twenty minutes from Clarksville, APSU and nearby Fort Campbell KY to the north and thirty minutes from downtown Nashville and all it has to offer to the south. The quiet woodsy setting and comfortable interior of White Duck provide a restful transition from a day of sightseeing or an exciting football or hockey game. **There is a $50 pet fee** Please include your pet during the booking process.

Top guest favorite
The Bridge House is seen suspended over a serene creek, framed by lush greenery. A calm water surface reflects the building and surrounding foliage. A gray dog stands on a rock in the foreground, appearing to enjoy the natural setting.
Place to stay in Ashland City
4.97 out of 5 average rating, 409 reviews

Bridge House over Blue Springs Creek

Magical in all seasons! Soothe your soul with an unforgettable escape, surrounded by nature and suspended twenty feet above a babbling brook! Listen to the rushing water and the bamboo whispering in the breeze, take in a sunset, or wade in the creek below. We hope you’ll enjoy this unique covered bridge conversion, expanding from bank to bank with a 50-foot front deck. Breakfast provided the first day includes fresh fruit, a half dozen eggs, and muffins, coffee and tea.

Top guest favorite
Cabin in McEwen
5 out of 5 average rating, 127 reviews

Peaceful Cabin + Deer | Cozy & Spotless | Retreat

Step into a space guests describe as tranquil, cozy, and exactly what they needed. Deer Ridge Cabin is designed for slowing down. Morning coffee on the porch, quiet evenings at the fire pit, and sightings of deer just passing through the property. Guests often say it’s one of the cleanest stays they’ve experienced and that “everything has been thoughtfully prepared.” With warm details throughout, it’s a place to reconnect, recharge, and create a stay you won’t forget.

Top guest favorite
A charming treehouse is nestled among tall trees, featuring earthy wooden tones and a rustic design. Soft outdoor lighting creates a cozy ambiance, while a path made of stones leads to the entrance. The treehouse is elevated, providing a unique vantage point into the surrounding nature.
Treehouse in Greenbrier
4.98 out of 5 average rating, 320 reviews

Nashville Luxury Dream Treehouse +Spa

This beautifully designed and luxurious treehouse sits on a ridge overlooking our creek. With only a 25min drive to downtown Nashville, you are tucked away amidst the towering hardwoods--away from the city noise. With careful attention to detail, the treehouse decor and design is meticulously curated to create an atmosphere of rest and beauty. This space is ideal for a couple, but can sleep four (twin beds in the loft). Parties are not permitted on the premises.

Top guest favorite
Two painted horses trot across a grassy field as the sun sets in the background, casting warm hues of orange and pink in the sky. Lush trees border the scene, enhancing a sense of tranquility in the natural landscape.
Cabin in Russellville
4.99 out of 5 average rating, 192 reviews

Keehn Hideaway-Hot tub/King bed/Horses/Secluded!

Come relax in our brand new Amish-made mini-HIDEAWAY! (Couples, friends, mother/daughter, business, or ME-time). We built our DREAM PLACE (with a brand new hot tub, GAS grill, and GAS firepit), and we are now sharing it with you! Located on 20 acres in the beautiful hills of Kentucky, you will be AMAZED at the sunsets and quietness. There are no near neighbors except the chirping birds and our horses to pet, watch, and feed. Come be refreshed!

Top guest favorite
A blue cabin is framed by greenery, featuring a wooden porch with two potted plants. A welcoming front door is complemented by a small American flag. Gravel pathways lead to the entrance, enhancing the rustic charm of the property.
Cabin in Big Sandy
4.97 out of 5 average rating, 113 reviews

"ROC 'n Dock | Lakefront Dock, Kayaks & Club Car"

"Stop scrolling and book this place." Our guests said it — we agree. ROC 'n Dock on Kentucky Lake has a covered private dock, kayaks, club car, screened porch, charcoal grill and smoker. Cleaned with plant-based Thieves products. Black Rifle Coffee stocked. 2 bedrooms, sleeps 6. 2 hrs from Nashville & Memphis.

Popular amenities for Oakridge vacation rentals

  1. Airbnb
  2. United States
  3. Tennessee
  4. Montgomery County
  5. Oakridge