Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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Top guest favourite
The lofted bedroom features a spacious bed with a light-colored, textured bedspread. Elegant lighting is provided by a chandelier above. Natural light enters through two windows, and a rustic wooden ceiling adds charm. Light-colored furnishings complement the cabin's warm ambiance.
Cabin in Hendersonville
4.99 out of 5 average rating, 141 reviews

Historic Log Cabin, Dreamy Loft Suite, Stone Frpl.

Historic Log Cabin built from reclaimed Civil War era logs, it’s recent extensive renovation revealed county doc’s showing it was developed by architect to the stars, Braxton Dixon forJohnny Cash. Perfect for artists or musicians retreat. Full kitchen, bath, loft honeymoon suite w/half bath, king bed, living/dining room, Stone fireplace & laundry. Sleeps 3 max. Deck overlooking treed acreage. Just 30 mins to Nashville attractions, Grand Ol Opry & airport, a quick drive to local restaurants etc

Top guest favourite
Treehouse in Franklin
4.99 out of 5 average rating, 151 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).

Guest favourite
The cabin features a two-story log structure with a welcoming entrance, framed by manicured greenery. A brick pathway leads to the front door, while large windows allow natural light to enhance the rustic charm of the exterior.
Cabin in Franklin
4.86 out of 5 average rating, 150 reviews

HUGE I-65 Hideaway Cabin/ Franklin/Ext stay disc.!

Located just off I-65, this spacious and historically rich cabin offers a one-of-a-kind stay that feels like stepping into a museum—with all the modern comforts you need. Relax on the huge back porch, grill out, or gather around the fire pit for cozy evenings. Inside, enjoy a lofted living space, fast Wi-Fi, and a washer/dryer for extended stays. Whether you're here for a weekend getaway, work trip or a longer escape, this cabin is perfect for families, remote workers, and history lovers alike.

Top guest favourite
The cottage is surrounded by trees, featuring a welcoming porch with seating. A red metal roof complements the light-colored siding, while large windows provide natural light. The spacious front yard is well-maintained, enhancing the cottage's inviting presence.
Home in Portland
4.96 out of 5 average rating, 145 reviews

Porchland Cottage - Countryside view-Pet Friendly

Porchland Cottage is a hillside retreat featuring views of the countryside with large porches & is the perfect place for a get-away or visiting the Nashville area. The cottage is just a few years old-extremely clean-8 min to town-40 min to Nashville-8 miles to SRMC. Located on the hillside of historic South Tunnel railroad & close to neighboring Gallatin. The land was occupied during the civil war by Union soldiers and has an area that is considered “The Fort”, although no structure exists.

Top guest favourite
A cozy studio space features a spacious bed with white linens, complemented by a decorative woven throw. A flat-screen TV is mounted above a charming electric fireplace, while a set of windows allows natural light to brighten the room. A small dresser and hanging hooks provide storage options.
Guest house in Portland
4.99 out of 5 average rating, 185 reviews

Howdie's Cottage near Nashville and Bowling Green

Our tiny studio guest cottage is located half way between Bowling Green,KY and Nashville,TN just 1.5 miles off I-65 @ exit 117. Private, beautiful farm views and convenient to everything Nashville and Southern KY has to offer. Enjoy Music city and all things Nashville. Head North for the day and visit Mammoth Caves or the Corvette Museum. Head back in the evening and we just might have a fire going in the fire pit! Short and long term guests welcome. Please inquire about long term pricing.

Guest favourite
A private pool area is surrounded by lush greenery and features a shimmering blue pool. Sun loungers sit along the edge, while a shaded seating area with an umbrella provides a space to relax. A hammock is visible in the background, inviting comfort.
Barn in Hendersonville
4.86 out of 5 average rating, 259 reviews

Hendersonville Homestead

After spending several years living in the heart of Nashville, we bought this nearly 3 acre property as newlyweds and have dreams of turning it into a mini-farm some day. We love having the space and quiet and want to share it with you! This AirBNB is a small, one-bedroom apartment attached to our workshop behind our main house. Our guests can enjoy the quiet space including a full kitchen, dining area, living room, and patio area. The pool is open from May-October with a few rules/hours.

Top guest favourite
The exterior of a rustic cabin features a combination of log siding and a green metal roof. A spacious covered porch welcomes guests, with large columns supporting the overhang. Surrounding trees provide shade and natural beauty, enhancing the serene rural setting.
Cabin in Russellville
4.95 out of 5 average rating, 164 reviews

Cozy Cabin with Private Walking Trail

Relax and retreat to this peaceful rural cabin with modern amenities and charming outdoor spaces situated on a working farm. Enjoy the walking trail through 10 acres of woods or swing while enjoying beautiful country views. Experience the best of both worlds in the historic 19th century cabin with a modern addition. A short drive to quaint downtown Russellville, Auburn, or Franklin KY each with plenty of shopping. The nearby Red River provides opportunities for kayaking, tubing or fishing.

Top guest favourite
A serene sunset is captured behind two leafless trees, casting a silhouette against a soft orange sky. Mist envelops the field, adding a layer of tranquility. The landscape extends softly into the distance, enhancing the peaceful rural atmosphere.
Home in Portland
4.92 out of 5 average rating, 219 reviews

Peaceful, chic farmhouse north of Nashville

We have free high-speed Wi-Fi - ideal for remote workers and TV bingeing. Perdue Farm is great for family gatherings, rejuvenation, and professionals. The interior is spacious with lots of natural light. The whirlpool tub offers relaxation and restoration. Outside, enjoy the wide open spaces. Soak in the amazing sunsets around the firepit in the back garden. Your stay at The Perdue Farm offers relaxation, fun family times, and a tranquil experience. Book your Tennessee adventure now!

Guest favourite
An inviting open-plan living space features a rich leather armchair and a sleek wood stove. Large windows frame views of the surrounding forest, with a dining area visible in the background. Natural wood accents and warm tones create a cozy atmosphere.
Cabin in Goodlettsville
4.94 out of 5 average rating, 513 reviews

Enjoy Nature at a Secluded Cabin near Nashville #2018038413

Made from reclaimed materials, this charming and newly constructed cabin has a vintage style that sits perfectly amongst the forest. It features a gorgeous open plan space and floor-to-ceiling windows that provide a 180-degree view of nature outside. Secluded on its own quiet 42 acres, the cabin lets you feel alone with nature. Further out, there's easy access to stores and restaurants with a few lovely places for antique shopping. Nashville itself is just a short drive away.

Top guest favourite
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, 288 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.

Superhost
The exterior of a renovated bungalow features a welcoming entrance with wooden steps leading up to a light blue door. Flanking the entrance are two chairs on a small porch, surrounded by well-maintained landscaping and tall trees, providing a serene outdoor atmosphere.
Home in Franklin
4.9 out of 5 average rating, 254 reviews

Cozy Boho Bungalow in Central Franklin KY

Enjoy this newly renovated 1940’s, 1 bedroom bungalow during your stay to Franklin, KY. Peaceful and modern indoor and outdoor spaces create a perfect environment for your next work trip, date night or weekend away. Minutes from I-65, this home accommodates the perfect day trip to Nashville, Mammoth Cave, or Amish Markets. **We welcome extended stays at a discount!** Just scroll down to the bottom and click "contact host" to ask us for your long stay discount!

Top guest favourite
The cabin features a spacious wraparound porch supported by sturdy columns, surrounded by greenery. Its wooden exterior complements the natural setting, with windows that provide ample light. Pine trees create a peaceful backdrop, and a lush lawn extends towards the forest.
Cabin in Cottontown
4.98 out of 5 average rating, 200 reviews

Candeight Cabin | Hike & Fish on 100 Acres

Welcome to Candlelight Cabin, tucked away at the trail head of the historic Dovetail Forest, a private 100 acre retreat conveniently located 30 minutes North of Nashville. Enjoy miles of hiking trails, a fire pit, fishing pond, golf range and a spacious lawn for recreation. We provide firewood, fishing gear, trail maps and recommendations for nearby dining and attractions. The Candlelight Cabin has fast wifi, Smart TV, a fully stocked kitchen and laundry room.

Popular amenities for Portland holiday rentals

  1. Airbnb
  2. United States
  3. Tennessee
  4. Sumner County
  5. Portland