Photo by Jon Ross

Portland holiday rentals

We found 66 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Portland that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include a hot tub and garden. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The friendly city of Portland awaits you

Enjoy the festivals and other features of Portland. This welcoming city attracts visitors thanks to its chocolate shops and university setting. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Portland

Are you hoping to discover attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Portland a fun place to get away to. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Sumner Crest WInery (4.5 mi / 7.2 km)
  • Kentucky Downs (4.8 mi / 7.7 km)
  • Legacy Golf Course (19.2 mi / 30.9 km)
  • Kenny Perry's Country Creek Golf Course (7.4 mi / 11.9 km)
  • Country Hills Golf Course (16.3 mi / 26.3 km)
  • Reid's Livery Winery (19.6 mi / 31.6 km)

Exploring the natural landscape of Portland

Whether you're looking for adventure or just want to spend some time taking in the scenery, Portland is a great place to get outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Triple Creek Park (12.7 mi / 20.4 km)
  • Drakes Creek Park (19.2 mi / 30.9 km)
  • Old Hickory Lake (21.9 mi / 35.3 km)
  • Portland City Park (0.2 mi / 0.4 km)
  • Laguardo Recreation Area (20.5 mi / 33 km)
  • Springfield Greenway (20.8 mi / 33.4 km)

Travelling to and around Portland

The nearest airport is in Nashville International Airport (BNA), located 32.2 mi (51.9 km) from the city centre.

Frequently asked questions

What is the best area to stay in Portland when booking a holiday rental?
When considering a holiday rental in Portland, Tennessee, a popular area to stay is the charming downtown district. This area offers a delightful blend of local shops, eateries, and a welcoming community spirit. One of the top attractions nearby is the historic Palace Theatre, which hosts various performances and events, providing a glimpse into the local culture. Additionally, the scenic Portland Greenway is great for leisurely walks or bike rides, allowing visitors to enjoy the natural beauty of the region.Another great option is the area surrounding the Old Hickory Lake, which offers a more tranquil setting. This picturesque spot is ideal for those looking to engage in outdoor activities such as fishing, boating, and hiking. The lake's serene environment is complemented by picnic areas and parks, making it a wonderful choice for families or couples seeking relaxation.
What is the most popular type of holiday rental accomodation in Portland?
In Portland, holiday houses are the most popular type of holiday rental, with about 20 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Additionally, there are around 12 cottages scattered in quieter neighbourhoods, offering a charming, rustic feel with amenities like outdoor seating and gardens. Several apartments, cabins, and condos also provide alternative options for travellers seeking different experiences.
Are there any family house rentals in Portland?
In Portland, Tennessee, there are several family-friendly house rentals available, making it a great spot for families seeking a getaway. The homes typically feature spacious living areas, full kitchens for preparing meals together, and outdoor spaces where children can play and explore. Many properties also offer amenities such as Wi-Fi and laundry facilities to ensure a comfortable stay.Visitors can enjoy nearby attractions, including local parks and recreational areas ideal for picnicking and outdoor activities.
Are there any remote work holiday rentals in Portland?
In Portland, Tennessee, there are around 44 remote work holiday rentals available, making it a great choice for those looking to blend work and leisure. Many of these properties come equipped with essential amenities for remote work, including high-speed Wi-Fi and designated workspaces.Travellers can expect a variety of accommodations, from modern apartments to spacious homes, often featuring comfortable living areas and fully equipped kitchens for convenient meal preparation. The town is situated near local parks and lakes, providing opportunities for outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Portland?
In Portland, Tennessee, popular holiday rental amenities include kitchens, allowing guests to prepare their own meals and enjoy home-cooked dining experiences. Many properties also feature patios or decks, providing inviting outdoor spaces for relaxation and socialising. Onsite parking is commonly available, making it convenient for travellers with vehicles. Additionally, some rentals come with porches or lanais, superb for enjoying the warm weather and local scenery.
When is the best time to visit Portland for a holiday rental?
The best time to visit Portland for a holiday rental is during September, when the weather is still pleasantly warm, and the summer crowds begin to dwindle. This month offers a fantastic opportunity to explore the city's vibrant culture, parks, and scenic views without the hustle and bustle of peak tourist season, which runs from July to September.During this peak season, particularly in July and August, Portland buzzes with activity, featuring numerous festivals, outdoor events, and a lively option that draws visitors from all over. Temperatures typically range from the mid-20s to low 30s Celsius, great for enjoying the city's renowned food scene and beautiful landscapes.If you're seeking a more tranquil experience, consider visiting in November. While this is considered the low season, it brings its own charm with fewer crowds, allowing for a more relaxed exploration of Portland's lively neighbourhoods and stunning fall foliage. Plus, you can still enjoy indoor attractions, such as the Portland Art Museum or the local craft breweries.
What are the top attractions in Portland?
In Portland, Tennessee, visitors can enjoy a variety of attractions that showcase the area's charm and natural beauty. The historic downtown area features quaint shops and local eateries, providing a glimpse into the town's rich heritage. The nearby Old Hickory Lake is a popular destination for outdoor enthusiasts, offering opportunities for fishing, boating, and picnicking along its scenic shores.For those interested in local history, the Portland Museum is a great stop, showcasing artifacts and exhibits that highlight the town's past. Additionally, the nearby Moss Wright Park presents ample green space for recreational activities, including walking trails, playgrounds, and sports facilities, making it ideal for families.
Are all fees included in the Portland holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Portland holiday homes with parking?
Stayz offers a wide selection of holiday homes in Portland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Portland holiday homes?
You can find great discounts on holiday homes in Portland on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Portland holiday home booking on Stayz?
To find Portland holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Portland?
A long-stay holiday home in Portland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Portland holiday home?
Book your Portland holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Portland?
Prices for holiday homes in Portland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Portland to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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