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, 141 reviews

Historic 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, 149 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, 145 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 living area features a blue sofa paired with a brown armchair. Natural light enters through large windows adorned with patterned curtains. A small table with a plant sits in the corner, complementing the space's relaxed atmosphere.
Guest suite in Mt. Juliet
4.94 out of 5 average rating, 535 reviews

Lakeside Luxury

This private residence has it all! Separate entrance with private kitchen/living room, bedroom & full bathroom. Old Hickory Lake is less than a minute from this location which has a free public boat launch and park that is a perfect place for picnics and to enjoy water sports, wildlife and nature. Downtown Nashville is less than 25 minutes away so you can enjoy the scenic lakeside activities during the day & then head downtown and enjoy all the sights and sounds that music city has to offer!

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
4.95 out of 5 average rating, 162 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, 219 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!

Guest favourite
A cozy studio space features a patterned bedspread on the queen-size bed. A small desk with a chair is positioned next to a mini fridge and microwave, with a coffee maker nearby. The bathroom door is open, revealing a well-lit entry.
Guest suite in Madison
4.93 out of 5 average rating, 203 reviews

Cozy 1 bath/1 bed retreat. 15 min from Downtown!

Private studio apartment attached to our house. It has its own entry and self check-in. No shared spaces. My wife and I live in the front portion of the home. We try to be really quiet & respectful of our guests, but it is a lived in home. ;-) Private 1-bedroom, 1-bathroom Mini fridge Microwave Coffee Maker Queen-size bed Fresh linens and towels High-speed Wi-Fi Free parking on premises Smart TV for streaming your favorite shows Air conditioning and heating Permit #2024002149

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, 288 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
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, 166 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.

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
4.9 out of 5 average rating, 254 reviews

Cozy Boho Bungalow in Central Franklin KY

Enjoy this newly renovated 1940’s, 1 bedroom bungalow 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 home accommodates the perfect day trip to Nashville, Mammoth Cave, or 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!

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, 200 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.

Guest favourite
A quaint cottage is framed by lush gardens filled with a variety of colorful flowers and greenery. The house features a welcoming porch and is surrounded by mature trees, creating a serene outdoor setting. Bright sunlight enhances the vibrant colors of the garden.
Cottage in Springfield
4.85 out of 5 average rating, 158 reviews

Peaceful Country Getaway with Horses & Gardens

Welcome to Birdsong Farm — a peaceful cottage on our 10-acre working horse farm. Relax on the porch at sunset, wander through gardens and orchard paths, and meet our friendly horses. We're just minutes from historic Springfield's shops, restaurants, and greenway, and 35 minutes from Nashville. Guests come here for quiet, nature, and creative inspiration — the perfect retreat for artists, couples, and anyone seeking a slower pace with modern comforts.

Popular amenities for Portland holiday rentals

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