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 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, 156 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, 213 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).

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
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, 200 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, 232 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 the house is showcased, featuring a red brick facade with a contrasting gray roof. Green bushes are neatly trimmed along the walkway, which leads to the entry. The lawn is well-maintained, and trees provide natural shading in the surrounding area.
Home in Franklin
4.96 out of 5 average rating, 180 reviews

Pet-Friendly Modern KY Retreat | Cozy 2BR Home

Enjoy this renovated 1940s retreat in Franklin, KY! Perfect for work trips, romantic getaways, or weekend escapes! Full kitchen, two bedrooms with queen beds, washer and dryer, and fast, reliable Wi-Fi. Pet-friendly and welcoming to all, it’s perfect for families, couples, or groups! Just minutes from I‑65, you can easily explore Nashville, Mammoth Cave, and local Amish markets. Have questions or interested in long-stay pricing? Click “Contact Host” before booking—we’re happy to help!

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, 108 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
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, 442 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 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, 346 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 favourite
Barn in Goodlettsville
4.97 out of 5 average rating, 326 reviews

The Barn at the Farm-Social Isolation at its best!

Adorable studio apartment located in the loft of a century-old barn in the heart of the hills of Goodlettsville. Located behind an 18th century farmhouse on a rural 25-acre farm, the barn is conveniently only 10 minutes from I-65 and, with no traffic, is a little over 30 minutes from Downtown Nashville. This quaint, secluded spot is the perfect jumping-off spot for your stay in Middle Tennessee! Please note that this is strictly a pet-free property.

Top guest favourite
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, 220 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!

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