Holiday rentals 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 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, 117 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.

Top guest favourite
Treehouse in Franklin
4.99 out of 5 average rating, 218 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, 156 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
A cozy outdoor seating area features bright blue chairs arranged around a table with a fire pit. Flames dance atop a bed of decorative stones, while a charcoal grill is visible in the background. A sunset casts warm hues across the open field.
Home in Portland
4.98 out of 5 average rating, 90 reviews

Romantic cozy cottage

- Quaint country cottage on a private lane - Perfect for couples or small family - King-sized bed in master bedroom; full-sized bed in second bedroom - Located between Nashville, TN & Bowling Green, KY off I-65; close enough to be in these locations & activities within an hour - Peaceful sunsets & scenic farm views - Fire pit and charcoal grill provided for outside enjoyment - Remodeled bathroom and all new flooring throughout (Cottage formerly known as "Bill's Cottage" to returning guests.)

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, 202 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 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, 233 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 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, 215 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 spacious living area features a large sectional couch and a wooden coffee table. A round mirror hangs on the wall above the couch, while two decorative woven baskets are displayed nearby. A floor lamp and a small desk with a plant complete the inviting space.
Flat in Portland
4.88 out of 5 average rating, 52 reviews

Wilkerson Lane Apartment

A 45 minute drive to Nashville but with a quiet, country setting. A location to free your mind and rest your body, enjoy being outdoors or inside in your own space. One queen bed and one large sectional couch can accommodate up to four people comfortably. TV, microwave, over, stove top and plenty of cooking supplies with complimentary coffee, flour, cooking oil and other necessary amenities. Equipped with a washer and dryer, and one full bathroom. Enjoy the patio with outdoor seating.

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.
Flat in Franklin
4.92 out of 5 average rating, 109 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.

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, 105 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.

Guest favourite
A welcoming entryway is adorned with a decorative wreath. A cozy seating area is visible in the background, with wooden flooring leading toward the staircase. A chandelier hangs from the ceiling, providing soft illumination to the space.
Home in Portland
4.97 out of 5 average rating, 105 reviews

The Yellow House - Hidden Gem in heart of Portland

This is a one of a kind home with beautiful wood working details, tall ceilings, and lux furnishings to make you feel relaxed and comforted after a long day of sightseeing. Treat yourself to a quiet retreat to Middle Tennessee and still have access to all of the sightseeing opportunities that the area has to offer. -Walking distance to shops and restaurants on Main Street -5.3 miles to The Mint Gaming Hall -32 miles to Bowling Green, KY -43 miles to Nashville, TN

Popular amenities for Portland holiday rentals