Holiday houses 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
Treehouse in Franklin
4.99 out of 5 average rating, 146 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.

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, 141 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.

Top Guest favourite
A cozy outdoor seating area features bright blue chairs arranged around a table with a fire pit. Flames dance atop a bed of decorative stones, while a charcoal grill is visible in the background. A sunset casts warm hues across the open field.
Home in Portland
4.99 out of 5 average rating, 74 reviews

Romantic cozy cottage

- Quaint country cottage on a private lane - Perfect for couples or small family - King-sized bed in master bedroom; full-sized bed in second bedroom - Located between Nashville, TN & Bowling Green, KY off I-65; close enough to be in these locations & activities within an hour - Peaceful sunsets & scenic farm views - Fire pit and charcoal grill provided for outside enjoyment - Remodeled bathroom and all new flooring throughout (Cottage formerly known as "Bill's Cottage" to returning guests.)

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, 533 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
4.96 out of 5 average rating, 160 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, 216 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
Guesthouse in Alvaton
5 out of 5 average rating, 27 reviews

The Best View on Fairview

Not your average stay! 🌅 We've prepared this stylish apartment for guests who desire more than just a place to sleep. 🛌 Spacious and bright, the well appointed space is designed for comfort.😍 The view from the picture window of the hillside and valley is fantastic and includes a 3 season view of Trammel Creek.🏞️ We have trees and meadows with a walking trail for you to explore as well as an ample yard to take full advantage of fair weather days. 🏃‍♀️🏃🏻‍♂️ *Staircase to entry

Top Guest favourite
Loft in Watertown
4.98 out of 5 average rating, 125 reviews

The Cedar Loft

The Cedar Loft is a beautiful space in the country nestled on 40 acres with a fantastic view. Conveniently close to I-40 with a driving time of 35 min. to the Nashville airport or 45 min. downtown Nashville. This brand new above garage loft has a private entrance. Kitchen offers granite counters, fridge, microwave, oven, and dishwasher. For laundry there is a washer/dryer combo. We offer wifi, have good cellular reception and offer an assortment of DVDs and board games.

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, 284 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, 164 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, 199 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.

Popular amenities for Portland holiday rentals

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