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Portland vacation rentals

We found 50 vacation rentals — enter your dates for availability

Discover a selection of 5 homes and other vacation rentals in Portland that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the amenities you need and want, such as parking and air conditioning. Whatever you're looking for, you'll find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

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Find out more about Portland

Why visit Portland

  • Outdoor Adventures: Portland, TN offers abundant opportunities for hiking and enjoying nature, especially in scenic areas like Shepherd Hills.
  • Rich History: Explore local history through museums and historic buildings that showcase the town's cultural heritage.
  • Charming Neighborhoods: Family-friendly neighborhoods provide budget-friendly experiences and a welcoming atmosphere.
  • Cozy Accommodations: Choose from a range of vacation rentals, including charming cabins and stylish condos, for a comfortable stay.
  • Romantic Spots: Discover picturesque locations perfect for couples seeking a scenic getaway.

Popular types of accommodation in Portland

Planning a getaway to Portland? You'll find a variety of popular vacation rentals to suit your needs. Choose from cozy houses, charming cabins, or stylish condos that offer all the comforts of home. Whether you're searching for rental listings in Portland, TN, or looking for apartments and homes, we have something for everyone. Explore the options available, including the inviting Portland Courtyard, and make your stay unforgettable.

  • Houses: The top choice for visitors in Portland, these homes offer spacious and comfortable accommodations for families, friends, or couples seeking a home-like experience.
  • Cabins: A close second, cabins provide a cozy retreat surrounded by nature, perfect for those wanting a rustic getaway.
  • Condos: These modern units are popular for their amenities and convenient locations, ideal for travelers seeking a blend of comfort and style.
  • Apartments: A practical option for guests, apartments offer flexibility and a local feel, making them suitable for longer stays.
  • Cottages: Charming and quaint, cottages are a delightful choice for those wanting a peaceful and picturesque escape.**

Top attractions in Portland

Portland, Tennessee, is an ideal destination for outdoor enthusiasts and couples seeking scenic getaways. Visitors can explore a variety of attractions, including urban parks, history museums, and historic buildings, making it perfect for those interested in culture, family outings, and outdoor experiences. Whether you're looking to relax in nature or immerse yourself in the local history, Portland has something to offer every traveler.

  • Cold Springs Museum: A charming historic building showcasing local culture and history, the Cold Springs Museum offers visitors a glimpse into Portland's rich past through engaging exhibits and artifacts.
  • Portland City Hall: This historic civic government building features stunning architecture and serves as a hub of local governance. Visitors can appreciate its cultural significance and the community spirit it embodies.
  • Portland City Park: A family-friendly urban park perfect for outdoor activities, Portland City Park provides ample green space for picnics, walking, and enjoying nature in a vibrant city setting.

Things to do recommended for couples

For a romantic escape in Portland, Tennessee, visit Sumner Crest Winery for a cozy atmosphere filled with entertainment vibes. Consider a short drive to Reid's Livery Winery, just 20 miles away, where you can enjoy beautiful scenery and delightful wines together.

Things to do recommended for families

Families visiting Portland, Tennessee can enjoy a fun-filled day at Beech Lake, perfect for swimming and picnicking. Explore the historic downtown area with charming shops and grab a bite at local eateries, ensuring a delightful experience for everyone.

Things to do recommended for groups

Experience a round of golf at Kenny Perry's Country Creek Golf Course, just 7 miles from Portland. For shopping and entertainment, visit The Streets of Indian Lake and catch a movie at Regal Streets of Indian Lake, both located 18 miles away, perfect for family fun.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Portland

If you're traveling with a group, heading out with your family, bringing along your pets, or seeking extended stays, be sure to use the right filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Portland with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Portland with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Portland: For many families, a vacation wouldn’t feel complete without their furry companion. If you can relate to this, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Portland: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Portland

Portland, Tennessee, offers a delightful blend of outdoor adventures and charming town vibes. Explore the scenic Shepherd Hills for breathtaking views and enjoy the friendly atmosphere that makes this city feel like home. Nearby, you’ll find family-friendly neighborhoods perfect for excursions and budget-friendly experiences. Whether you’re seeking romantic spots or a taste of country living, Portland's appeal is undeniable, promising memorable moments and warm hospitality throughout your stay.

  • Goodlettsville: Located 21 miles from Portland, Goodlettsville is a vibrant city that offers a blend of family-friendly activities and business opportunities. This charming locale is known for its shopping areas, including popular malls and centers that cater to both leisure and retail therapy. Explore local landmarks such as sports facilities and stadiums, perfect for catching a game or attending community events. With a welcoming atmosphere and convenient amenities, Goodlettsville is an ideal stop for those looking to enjoy a bustling city experience.
  • Gallatin: Just 14 miles from Portland, Gallatin is a picturesque city that invites visitors to immerse themselves in its scenic beauty and outdoor adventures. Known for its recreational areas and hiking trails, Gallatin is perfect for nature lovers and couples seeking a romantic getaway. Highlights include nearby lakes and a beautiful beach, as well as access to the stunning national state park. With abundant opportunities for exploration and relaxation, Gallatin is a perfect destination for outdoor enthusiasts and those looking to enjoy the great outdoors.
  • Franklin: Situated only 10 miles from Portland, Franklin is a charming city known for its adventurous spirit and outdoor experiences. Visitors can enjoy a variety of attractions, including campgrounds, a water park, and numerous recreational areas. The city's proximity to a racetrack and national state park further enhances its appeal for those seeking adventure and natural beauty. With its rich history and vibrant community, Franklin provides an unforgettable experience filled with exploration and romance.

Best time to go to Portland

If you're planning a trip to Portland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.0°F (2.2°C)Light RainMostly CloudyAverageSlightly Low
February40.3°F (4.6°C)Light RainMostly CloudyAverageSlightly Low
March48.7°F (9.3°C)Light RainMostly CloudyAverageAverage
April57.2°F (14.0°C)Light RainMostly SunnySlightly HighAverage
May66.6°F (19.2°C)Light RainMostly SunnyAverageAverage
June74.7°F (23.7°C)Light RainMostly SunnyAverageSlightly High
July77.4°F (25.2°C)Light RainMostly SunnySlightly HighAverage
August75.9°F (24.4°C)Light RainMostly SunnyAverageSlightly High
September70.3°F (21.3°C)Light RainMostly SunnySlightly HighSlightly High
October59.2°F (15.1°C)Light RainMostly SunnySlightly LowAverage
November47.7°F (8.7°C)Light RainMostly SunnySlightly LowAverage
December41.5°F (5.3°C)Light RainMostly CloudySlightly LowSlightly Low

Booking with Vrbo is simple

Are you hoping to keep costs down on your upcoming journey? Being flexible with your travel dates can really help, as prices can vary quite a bit. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner has its rewards. By enrolling in our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash on eligible reservations. Sign up now and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new trips, manage your travel arrangements, and keep track of your bookings. You can easily find your saved or reserved properties organized into categories like Potential, Upcoming, or Current Trips. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The friendly city of Portland awaits you

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

Sightseeing in and around Portland

Are you hoping to find attractions to see during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Portland a fun spot to vacation. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Kentucky Downs (4.8 mi / 7.7 km)
  • Kenny Perry's Country Creek Golf Course (7.4 mi / 11.9 km)
  • Legacy Golf Course (19.2 mi / 30.9 km)
  • Sumner Crest WInery (4.5 mi / 7.2 km)
  • Country Hills Golf Course (16.3 mi / 26.3 km)
  • Windtree Golf Club (23.5 mi / 37.7 km)

Exploring the natural landscape of Portland

Whether you're looking for fun outdoor activities or just want to take in the scenery, Portland is a great place to get outside. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Triple Creek Park (12.7 mi / 20.4 km)
  • Drakes Creek Park (19.2 mi / 30.9 km)
  • Rockland Recreation Area (20.9 mi / 33.7 km)
  • Old Hickory Lake (21.9 mi / 35.3 km)
  • Portland City Park (0.2 mi / 0.4 km)
  • Ridgetop Station Park (18.7 mi / 30 km)

Traveling to and around Portland

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

Frequently asked questions

What is the best area to stay in Portland when booking a vacation rental?
When planning a vacation rental in Portland, Tennessee, one of the best areas to consider is the charming downtown district. This area offers a vibrant atmosphere with a mix of local shops, restaurants, and cultural attractions. Staying in downtown Portland puts you within walking distance of the historic Portland Depot, which showcases the town's rich railroad history, and the nearby Portland Arts and Cultural Center, where you can enjoy local art and community events.

Another great area to explore is the scenic outskirts of town, particularly near the beautiful Old Hickory Lake. This region is great for those who enjoy outdoor activities, as it provides ample opportunities for fishing, boating, and hiking. The lake area is also home to several recreational parks, making it a peaceful retreat for nature lovers.

In terms of vacation rental availability, both the downtown district and the lake area offer a variety of properties, ranging from cozy cottages to spacious homes, ensuring you can find the great fit for your stay.
How much does it cost to rent a vacation home in Portland?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Portland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Portland vacation house rentals?
You can find great discounts on house rentals in Portland on Vrbo, 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.
Where are the best areas for renting a beach house in Portland?
For renting a beach house in Portland, Tennessee, travelers should focus on the areas surrounding Old Hickory Lake, which is a popular destination for water activities and relaxation. The neighborhoods along the lake, particularly near Sanders Ferry Park, offer vacation rentals with easy access to the water, providing opportunities for swimming, fishing, and boating.

Many properties in this area come equipped with amenities such as private docks, outdoor decks, and spacious backyards ideal for gatherings. Some rentals may include features like fire pits and barbecue grills, great for enjoying the warm Tennessee evenings by the water.

Additionally, the nearby Long Hollow area offers a mix of scenic views and proximity to local parks, which can enhance the beach house experience. Properties here often include cozy interiors, fully equipped kitchens, and comfortable living spaces, making them suitable for families or groups looking for a lakeside retreat.
What is the most popular type of vacation rental accomodation in Portland?
In Portland, Tennessee, vacation houses are among the most popular types of rentals, with several available throughout the area. These houses typically offer spacious living areas, fully equipped kitchens, and outdoor spaces such as patios or yards—ideal for families or groups looking for a comfortable home base. Additionally, cabins are also a favored choice, providing a rustic charm with amenities like fireplaces and proximity to nature, making them great for those seeking a peaceful retreat. Cottages and condos are other options that travelers can find, each with unique characteristics and amenities suited for different preferences.
Are there any family house rentals in Portland?
In Portland, Tennessee, there are several family-friendly house rentals available, making it a great destination for groups and families. Properties in the area often feature spacious living rooms, fully equipped kitchens for preparing meals together, and outdoor areas where kids can enjoy playtime. Many homes come with amenities such as Wi-Fi and laundry facilities, ensuring a comfortable stay.

Visitors can explore nearby attractions, including the scenic parks and recreational areas that offer opportunities for hiking and picnicking. The local community provides an inviting space, with charming shops and restaurants for families to enjoy.
Can I find long-stay vacation rentals in Portland?
A long-stay vacation rental in Portland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Portland?
In Portland, Tennessee, travelers can find several pet-friendly vacation house rentals that cater to those looking to enjoy a comfortable stay with their furry companions. Many of these homes are equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces, making them ideal for families or groups.

The rentals are often situated near charming local parks, providing easy access for pet owners to enjoy leisurely walks or playtime with their dogs. Nearby parks might include the picturesque Drakes Creek Park, which offers trails and open areas great for outdoor activities.
Are there any remote work vacation rentals in Portland?
In Portland, Tennessee, there are several vacation rentals suitable for remote work. Travelers can expect properties that come equipped with essential amenities such as Wi-Fi, comfortable desk chairs, and dedicated workspaces, making it easy to stay productive while enjoying a getaway. The town itself offers a tranquil environment, superb for focusing on work, while also providing opportunities for relaxation. Local attractions, such as parks and nearby lakes, add to the appeal, allowing for outdoor breaks and leisure activities after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Portland vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Portland with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
What are popular rental amenities in Portland?
In Portland, Tennessee, popular vacation rental amenities include WiFi, kitchens, patios, coffee and tea makers, and decks or patios. These features cater to travelers looking for convenience and comfort during their stay. Most rentals offer fully equipped kitchens, allowing guests to prepare their meals, while patios and decks provide outdoor spaces for relaxation. WiFi access ensures that visitors can stay connected, making it easier to plan activities or work remotely if needed.
When is the best time to visit Portland for a vacation rental?
September is the most popular time to visit Portland, Tennessee, as it marks the tail end of the peak travel season, which runs from July to September. During these summer months, visitors flock to the area to enjoy outdoor activities, picturesque parks, and vibrant local events. The warm weather, with temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, creates a friendly space for sightseeing and exploring the natural beauty of the region.

As September rolls in, you can still relish the benefits of summer while enjoying a slightly quieter environment. This month offers a delightful mix of warm days and cooler evenings, superb for leisurely strolls along the waterfront or taking in the stunning views at local parks. The community often hosts various fall festivals, providing a great way to experience the local culture and cuisine.

For those looking for a more budget-friendly option, November presents a wonderful opportunity to explore Portland without the hustle and bustle of peak season. During this month, you can appreciate the tranquility of the town while enjoying the beautiful autumn landscapes. The crisp air and vibrant fall colors make for an enchanting backdrop, ideal for hiking and outdoor photography.

Ultimately, the best time to book a vacation rental in Portland depends on your preferences for social activity and weather.
How early should I book a Portland vacation rental?
Book your Portland vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Portland home rental booking on Vrbo?
To find Portland vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Portland vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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