Holiday houses in Portland

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Top-rated holiday rentals in Portland

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

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Top Guest favourite
The exterior of a single-story house is shown, featuring a large deck and a clear pathway leading to the entrance. Nearby, a vintage Coca-Cola sign adds a nostalgic touch against a rustic wooden structure. Lush greenery surrounds the property, providing a tranquil setting.
Cottage in Ashland City
4.92 out of 5 average rating, 116 reviews

The Little House by the Woods

Hunt, Hike & More! A tranquil retreat with all the comforts of home. Calming colors, lots of natural light. Enjoy Tennessee's natural beauty with a subtle homage to our favorite Gulf Coast beaches. "The Little House by the Woods" is on a ridge surrounded by trees. Across the road is Cheatham Wildlife Management Area with 20,000 acres of hill country with hiking, hunting and birdwatching. You'll have easy access to so many parks, recreation and all that Nashville (30 min. away) has to offer.

Top Guest favourite
The loft honeymoon suite is illuminated by a decorative chandelier, enhancing the rustic charm of reclaimed wood walls. A spacious bed is positioned under a vaulted ceiling, while a vintage-style mirrored vanity is nearby. Natural light enters through a small window, creating a serene atmosphere.
Cabin in Hendersonville
4.99 out of 5 average rating, 151 reviews

JuneBug 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, 190 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 spacious living area features hand-hewn log walls and wooden beams, showcasing rustic charm. A large dining table surrounded by wooden chairs is positioned on a patterned rug. Open spaces lead to a kitchen area, enhancing the communal ambiance of the cabin.
Cabin in Franklin
4.86 out of 5 average rating, 153 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
Home in Portland
4.96 out of 5 average rating, 151 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 spacious two-story house is positioned amidst lush greenery, featuring a black metal roof and white siding. The yard is expansive, bordered by varied trees. A gravel driveway leads alongside the property, showcasing a peaceful countryside setting under a bright blue sky.
Farm stay in Bowling Green
4.92 out of 5 average rating, 455 reviews

Mammoth Cave/Farm

🏡 Out of office, into the farmhouse. Ditch the city, find your soul. This house offers good vibes especially if you like having a cup of coffee in your hand on the porch with a beautiful sunset. Nature is calling. You should answer. Sunrise, sunset, and repeat. Fresh air = instant mood boost and wake up happy the farmhouse way. Zero traffic and all the modern amenities. The best ice cream place is less than 3 miles away. Mammoth Cave, Corvette MuseumAnd Beech Bend are some attractions nearby!

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.
Guesthouse in Portland
4.99 out of 5 average rating, 194 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 wooden swing hangs on a covered porch, adorned with decorative pillows and a knitted throw blanket. Sunlight filters through the trees, creating a serene view of the green yard and nearby home beyond.
Home in Franklin
4.9 out of 5 average rating, 286 reviews

Pet-Friendly Boho Bungalow | Charming Retreat

Escape to this renovated 1940s boho bungalow in Franklin, KY. Perfect for couples, work travelers, or weekend getaways, this cozy retreat features a relaxing backyard pergola, fire pit, and easy access to Nashville, Mammoth Cave, and local 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! Dog-friendly with self check-in, fast Wi-Fi, and easy access to I-65 for exploring southern Kentucky!

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
4.94 out of 5 average rating, 198 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 cozy firepit area is framed by a pergola adorned with string lights, inviting relaxation during sunset. Multiple seating options, including two adirondack chairs and a hanging chair, surround the central fire, set against an expansive grassy backdrop.
Home in Portland
4.93 out of 5 average rating, 228 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!

Top Guest favourite
The cottage is surrounded by lush greenery and tall trees, offering a serene and natural setting. A winding gravel path leads to the entrance, showcasing landscaping with various plants. Warm sunlight filters through the trees, enhancing the peaceful ambiance of the rural environment.
Cottage in Hendersonville
4.99 out of 5 average rating, 181 reviews

Cozy Cottage Wooded Retreat

Our cottage is cozy, private, and safe! It is fully equipped to make your stay as enjoyable and carefree as possible. We have WIFI, 2 TV's Roku on both TVs, a Bose Radio with CD's, a DVD player with movies. We have a Coffee Station with Keurig & pods, a Mr Coffee with a coffee grinder. Completely equipped Kitchen. Tub/shower combo. Lots of privacy on your own back deck and your own private firepit out your back door. You will see deer and wild turkey. You must be 25 or older

Top Guest favourite
Treehouse in Greenbrier
4.98 out of 5 average rating, 325 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.

Popular amenities for Portland holiday rentals

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