Holiday houses in Portland

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Top-rated holiday rentals in Portland

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Top Guest favourite
The cabin exterior features a rustic wooden facade with a tin roof, nestled among tall trees. Warm light glows from the windows, creating a cozy ambiance in the forest setting, while a path leads up to the entrance surrounded by natural foliage.
Cabin in Greenbrier
4.97 out of 5 average rating, 225 reviews

Cozy Nashville Cabin in Woods w/ Spa

Only 25min from Nashville Broadway, East Nashville, Ryman Auditorium, Grand Ole Opry, and 30min from Nashville Airport BNA; We've prepared an intentional, cozy space, a respite from the city noise. With ample parking, free wifi, back deck and chosen premium mattresses, natural fiber linens, and toxin free cleaners/detergents; Our cabin guest house is nestled on the edge of an unfenced creek ridge surrounded by tall woods over. We love to provide coffee, farm fresh eggs and butter for our guests.

Top Guest favourite
A charming treehouse design is perched above the forest floor, featuring large windows that invite natural light. A spacious deck with a railing extends from the structure, and wooden stairs lead down to a gravel area with stacked firewood nearby. The surrounding trees create a secluded setting.
Treehouse in Franklin
4.99 out of 5 average rating, 131 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, 144 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.

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, 138 reviews

Modern KY Retreat | Cozy 2 Bedroom Home

Enjoy this newly renovated 1940’s, retreat 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 cozy retreat accommodates the perfect day trip to Nashville, Mammoth Cave, or local Amish Markets throughout KY. All are welcome! Scroll down to the bottom and click "contact host" to ask us any questions you may have about the space or long stay pricing before booking.

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, 255 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
4.96 out of 5 average rating, 152 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, 214 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 log cabin exterior features a private entrance leading to the guest suite. The structure showcases natural wooden walls and stone accents, surrounded by green trees. A spacious front porch is visible, along with stairs leading up to the entry. The area is inviting and set in a serene environment.
Guest suite in Bethpage
4.99 out of 5 average rating, 175 reviews

Cabin On The Creek! Private Suite

Our log cabin home is located on 30 acres just north of Gallatin, TN. Perfect location to enjoy Nashville and all it has to offer! Stay in our downstairs guest suite which has a private entrance, living space, bedroom and full bath. The guest suite is in the lower level of our cabin and is a naturally cool environment, so it's great for sleeping (no thermostat). We are only about a 50 min drive from the heart of downtown Nashville and Old Hickory Lake is just 20 minutes away!

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
5 out of 5 average rating, 160 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. You may see deer and wild turkey . Gas Grill provided. plenty of parking. NO PETS ALLOWED.

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, 192 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.

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, 151 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!

Top Guest favourite
The log cabin is illuminated by warm outdoor lighting, showcasing its rustic charm against a backdrop of lush greenery. A spacious porch wraps around the front, providing ample seating and scenic views of the surrounding landscape.
Cabin in Cross Plains
4.98 out of 5 average rating, 113 reviews

"River House" Log Cabin Nestled near the Red River

Come stay on this secluded 33 acre farm, just 35 miles North of Nashville, 35 miles South of Bowling Green, and close to several historic sites and antique stores. This log cabin lies at the end of a dead end road, nestled near the small, southern fork of the Red River, with about 1/4 mile stretch of the river bordering the property. Easy access to walk to the creek. RV carport with electrical hookup available right outside of the cabin.

Popular amenities for Portland holiday rentals

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