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 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, 155 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, 209 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).

Superhost
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, 154 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, 154 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
An aerial view captures the spacious property surrounded by lush greenery and trees. The single-story home features a brown roof and is positioned on a grassy area, creating a serene country atmosphere. The expansive grounds provide ample natural space for relaxation and outdoor activities.
Home in Cottontown
4.92 out of 5 average rating, 114 reviews

The Honey Branch

The Honey Branch sits on a little over five acres but feels like being on hundreds of acres. While middle Tennessee is growing at a rapid pace, things on Pee Dee Branch Road would tell a different story. Less than 30 miles from Broadway, The Grand Ole Opry and Opry Mills Mall. Less than 10 miles from Indian Lake Shopping in Hendersonville, downtown Gallatin and White House. Most recently, The Honey Branch has upgraded its internet capability with high speed fiber. Beds are 2 queens, 1 full.

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
4.88 out of 5 average rating, 295 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, 208 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.

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
4.91 out of 5 average rating, 231 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
A spacious living area features a mix of leather and fabric seating arranged around a central coffee table. Exposed brick walls add character, while a ceiling fan provides airflow. A flat-screen television is positioned near a decorative fireplace, and a soft area rug enhances comfort.
Apartment in Franklin
4.91 out of 5 average rating, 105 reviews

Lovely Historic Spot ~ Walk to the Square!

This special place is close to everything, making it easy to plan your visit. Newly remodeled ground level apartment in a historic home- you will be close to shopping and restaurants in downtown Franklin, Kentucky. Walk to the square and enjoy your search for cool finds in local shops and great food. Easy access to Nashville (45 minutes), Bowling Green (25 minutes), Mammoth Cave, the Corvette Museum, and so much more. About 5 minutes to I-65 makes getting in and out of Franklin easy.

Top Guest favourite
Cottage in Hendersonville
4.99 out of 5 average rating, 186 reviews

Cozy Cottage Wooded Retreat

Our cottage is cozy, 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 to book

Top Guest favourite
A dining area is highlighted by a gray table surrounded by four cushioned stools. A decorative centerpiece with natural elements sits atop the table. A large clock adorns the wall, and natural light enters through the nearby window, illuminating the room's neutral tones.
Home in Portland
4.93 out of 5 average rating, 101 reviews

The Getaway.Need a break from big city living?

Visiting lovely Middle Tennessee or Nashville, for business or pleasure? Need a break from big city living? Let “The Getaway” provide you with a quiet place to relax. Enjoy a delicious cup of coffee on the outdoor patio while you take in the beautiful view. There is a Coffee Bar, fully stocked Kitchen and Outdoor Patio for those cozy mornings or relaxing evenings after a round of golf, site seeing or long day of work. The whole family can enjoy a peaceful place to stay.

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, 340 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