
Holiday houses in Portland
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Top-rated holiday rentals in Portland
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The Little House by the Woods
Hunt, Hike & More! A tranquil retreat with all the comforts of home. Calming colors, lots of natural light. Enjoy Tennessee's natural beauty with a subtle homage to our favorite Gulf Coast beaches. "The Little House by the Woods" is on a ridge surrounded by trees. Across the road is Cheatham Wildlife Management Area with 20,000 acres of hill country with hiking, hunting and birdwatching. You'll have easy access to so many parks, recreation and all that Nashville (30 min. away) has to offer.

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

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).

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.

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.

Mammoth Cave/Farm
🏡 Out of office, into the farmhouse. Ditch the city, find your soul. This house offers good vibes especially if you like having a cup of coffee in your hand on the porch with a beautiful sunset. Nature is calling. You should answer. Sunrise, sunset, and repeat. Fresh air = instant mood boost and wake up happy the farmhouse way. Zero traffic and all the modern amenities. The best ice cream place is less than 3 miles away. Mammoth Cave, Corvette MuseumAnd Beech Bend are some attractions nearby!

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.

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!

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.

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!

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 and your own private firepit out your back door. You will see deer and wild turkey. You must be 25 or older

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
Other great holiday rentals in Portland

Southern Comfort

Eagle Mountain Luxury Cabin | River View + 1-Gig

3 BR Historic Downtown Home w/ Porch + Pool Table

* Stylish 3BR Getaway by LCS Signature Properties

The Parlor

The Guest Suite

Tiny Hilltop Hideaway

The Cabin at Roney Creek Ranch
Destinations to explore
- Western North Carolina Holiday rentals
- Atlanta Holiday rentals
- Nashville Holiday rentals
- Gatlinburg Holiday rentals
- Pigeon Forge Holiday rentals
- Indianapolis Holiday rentals
- Asheville Holiday rentals
- Louisville Holiday rentals
- Southern Indiana Holiday rentals
- St. Louis Holiday rentals
- Cincinnati Holiday rentals
- Upstate South Carolina Holiday rentals
- Bridgestone Arena
- Nissan Stadium
- Vanderbilt University
- Music City Center
- Mammoth Cave National Park
- Belmont University
- Grand Ole Opry
- Nashville Shores Lakeside Resort
- Nashville Zoo at Grassmere
- Beech Bend
- The Parthenon
- Radnor Lake State Park
- Ryman Auditorium
- Bicentennial Capitol Mall State Park
- Opry Mills
- Country Music Hall of Fame and Museum
- First Horizon Park
- Tennessee State University
- Lipscomb University
- Tennessee Performing Arts Center
- National Corvette Museum
- Beachaven Vineyards & Winery
- Adventure Science Center
- Cumberland Park





