
Holiday rentals in Portland
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Top-rated holiday rentals in Portland
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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).

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.

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.

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!

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!

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.

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.

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.

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.

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.

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!
Popular amenities for Portland holiday rentals
Other great holiday rentals in Portland

Romantic cozy cottage

3 BR Historic Downtown Home w/ Porch + Pool Table

Farmside Apartment

The Barn at Salem Acres

Sumner Sunsets - Quiet Area w/ Room for the Fam

Storybook Cottage near Leipers Fork, TN

Modern Home North of Nashville - Sleeps 7

Tiny Hilltop Hideaway
Destinations to explore
- Nashville Holiday rentals
- Atlanta Holiday rentals
- Gatlinburg Holiday rentals
- Indianapolis Holiday rentals
- Pigeon Forge Holiday rentals
- St. Louis Holiday rentals
- Asheville Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Memphis Holiday rentals
- Chattanooga Holiday rentals
- Birmingham Holiday rentals
- Mammoth Cave National Park
- Nissan Stadium
- Vanderbilt University
- Bridgestone Arena
- Grand Ole Opry
- Music City Center
- Nashville Shores Lakeside Resort
- Belmont University
- Ryman Auditorium
- Opry Mills
- Nashville Zoo at Grassmere
- Tennessee State University
- Beech Bend
- The Parthenon
- Radnor Lake State Park
- Bicentennial Capitol Mall State Park
- Lipscomb University
- Country Music Hall of Fame and Museum
- First Horizon Park
- Ascend Amphitheater
- Beachaven Vineyards & Winery
- Adventure Science Center
- Tennessee Performing Arts Center
- Cumberland Park





