Portland Vacations from $484

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Portland vacation packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Indianapolis, IN - Southport
Ironworks Hotel Indy
Windsor Park Pad apt 2 min to Mass Ave With AC
The village
Executive Inn
Don't see what you're looking for?
See all available trips from Columbus to Portland
View all trips

Portland Hotel Deals

Holiday Inn Express & Suites Portland by IHG

Holiday Inn Express & Suites Portland by IHG

2.5 out of 5
100 Holiday Dr Portland IN
Fully refundable
$110 nightly
The price is $123 total per night from Apr 19 to Apr 20
$123 total
Apr 19 - Apr 20
Total with taxes and fees
9.2/10 Wonderful! (364 reviews)
Outstanding - highest rating possible - in all regards of customer service!

Reviewed on Apr 7, 2026

Holiday Inn Express & Suites Portland by IHG
Motel 6 Portland, IN

Motel 6 Portland, IN

2 out of 5
1147 US-27 Portland IN
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $84 total per night from Apr 14 to Apr 15
$84 total
Apr 14 - Apr 15
Total with taxes and fees
6.8/10 (82 reviews)
When we arrived we were told no rooms were available as they had no water. Told us they called us, but they didn’t leave a message letting us know the room reservations was canceled

Reviewed on Mar 9, 2026

Motel 6 Portland, IN
Hoosier Inn

Hoosier Inn

2.5 out of 5
1620 N Meridian St Portland IN
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $91 total per night from Apr 15 to Apr 16
$91 total
Apr 15 - Apr 16
Total with taxes and fees
8.8/10 Excellent! (138 reviews)
Excellent staff

Reviewed on Feb 13, 2026

Hoosier Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Portland Vacation Packages

Things to do near Portland

Portland, Indiana, is an ideal destination for sports and outdoor enthusiasts, offering exciting activities like motor racing and fishing resorts. Visitors can enjoy day tours and explore local culture through art galleries. With its recreational areas, Portland provides a perfect backdrop for adventure and relaxation, making it a great spot for a memorable vacation.

Shopping

If you're up for a drive, visit Southway Centre Shopping Center, located 29 miles from Portland. This shopping center offers a mix of business and family-friendly vibes, making it a great spot to find unique gifts and souvenirs during your stay.

Recreation

At Winchester Golf Club, enjoy a round of golf surrounded by scenic landscapes just 19 miles from Portland. For a more tranquil experience, visit Saint Henry North Park and Coldwater Memorial Park, both 18 miles away, where you can unwind in serene environments perfect for relaxation and wellness.

Adventure

Eldora Speedway offers thrilling motor racing excitement, located 20 miles from Portland, perfect for adrenaline seekers. Similarly, Winchester Speedway, situated 18 miles away, promises high-speed action and adventure vibes. For a different experience, visit Cardinal Creek Tennis Center, 28 miles away, where you can enjoy energetic tennis matches in a lively atmosphere.

Nightlife

In Portland, Indiana, experience a cozy nightlife with local bars and cafes. Head to the charming downtown area for friendly pubs and live music venues, where you can enjoy a relaxed atmosphere and connect with locals over drinks and entertainment.

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

Find the best attractions near Portland

Portland, Indiana, offers an exciting blend of sports and outdoor adventures, making it a perfect vacation spot. Visitors can explore captivating monuments, historic sites, and national parks that reflect the region’s culture and history. Whether you're looking for family-friendly activities or a chance to immerse yourself in nature, Portland has something for everyone. Don’t forget to check out local resorts and attractions for a complete experience of this charming town.

  • Limberlost State Historical Site: Immerse yourself in the rich history and culture of the Limberlost State Historical Site, located 11 miles from Portland. This historic site offers a glimpse into the life of author Gene Stratton-Porter, surrounded by beautiful natural scenery and cultural exhibits that celebrate the area's heritage.
  • Berne Clock Tower: Experience a piece of local history at the Berne Clock Tower, situated 15 miles from Portland. This charming monument stands as a symbol of the community and features stunning architecture, making it a perfect spot for photos and appreciating the town's cultural vibes.
  • Lehman Park: Enjoy outdoor activities at Lehman Park, located 15 miles from Portland. With its eco-friendly environment and family-friendly amenities, the park is ideal for picnics, nature walks, and children's play, providing a relaxing escape for visitors of all ages.

Best time to go to Portland

The best time to visit Portland is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.8°F (-2.9°C)Light RainMostly CloudyAverageSlightly Low
February29.5°F (-1.4°C)Light RainMostly CloudySlightly LowAverage
March40.5°F (4.7°C)Light RainMostly CloudyAverageAverage
April50.5°F (10.3°C)Light RainMostly CloudyAverageAverage
May62.1°F (16.7°C)Light RainMostly SunnyAverageSlightly High
June70.0°F (21.1°C)Light RainMostly SunnyAverageAverage
July73.0°F (22.8°C)Light RainMostly SunnySlightly HighSlightly High
August71.2°F (21.8°C)Light RainMostly SunnySlightly HighAverage
September65.5°F (18.6°C)Light RainMostly SunnySlightly HighSlightly High
October54.3°F (12.4°C)Light RainMostly SunnySlightly LowAverage
November41.9°F (5.5°C)Light RainMostly SunnyAverageSlightly Low
December33.6°F (0.9°C)Light RainMostly CloudySlightly LowSlightly Low

Tips to save on your trip to Portland

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically November to January) for more affordable package holidays to Portland.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Portland Essential Information

Language
English
Currency
U.S dollars
Population
6,200
Max Temp Winter
35ºF
Max Temp Summer
80ºF

More vacations you might like

Frequently asked questions

How much does a Portland vacation package cost?
Offering great value package deals from $484 on Expedia, you'll be pleasantly surprised at how much a vacation to Portland costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Portland?
February, May and June are great times to search for cheap Portland vacation packages. Choosing to travel in quieter months means you can usually find reduced prices on flights and accommodations.
How many days is enough for Portland?
The ideal length of your Portland vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you time to tick off all the main sights and discover some hidden gems along the way.
How to find the best Portland package deals?
Use Expedia's filters to help you find some terrific Portland package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Portland package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Portland vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and stays individually. Better still, you can tailor your Portland trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Portland?
If you have your Portland travel dates finalized, book as soon as you can to score some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Portland vacation packages?
If you're like us, you love discovering new places but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Portland trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.