No vacation in the Pacific Northwest should omit Portland from the itinerary. This Oregon port city is bustling with excitement and culture, making it an ideal destination for those looking to get out and explore. If your vacation dollar needs to stretch, you’re in luck. Many Portland vacation rentals are accompanied by discounts and specials, so it’s possible to tour within your budget. Below, we’ll dive into some of the ways you can save money while still having a blast.

Portland’s Seasons and Peak Tourist Times

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Spring showers will definitely be around, but it’s possible to dodge the raindrops and enjoy the spring blossoms that seem to be everywhere. Temperatures will range from the 40s in early spring up to the 60s by the end of spring. Summer is the peak tourist season in Portland, largely due to the comfortable temperatures and dry weather. Plenty of festivals are scheduled every year, giving vacationers plenty to do. As temperatures drop in the autumn, so do the tourist numbers. Although the weather can get iffy, visitors can still stay busy in museums and shops during the fall. Winter is cold in Portland — no doubt about it. Visiting during the holiday season promises much to do with festivals and celebrations. Lodging rates tend to match the peak tourist times, so expect to pay top dollar for vacation rentals from late spring through early fall.

Ideas for Getting the Best Price on Vacation Rentals

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You can try a number of strategies to save money on vacation rentals in Portland. Aside from visiting in the off-season, you might be able to snag a discount if you book a stay that spans seven or more days during the winter. Perusing websites and social media feeds will often enable you to discover online discount codes, which you can enter if you book online. You might also try waiting to book at the last minute. If your schedule permits, you can often get a decent discount if you book only days or hours before your stay begins.

Don’t Forget Vacation Packages

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Some property management companies offer exciting vacation packages that can help you stretch your vacation budget a little farther. With a house or condo reservation, you’ll receive a package that can include special discounts or even free passes to area attractions. You might get in free to one of the many museums in downtown Portland, or perhaps you’ll have a nice discount at one of the many local restaurants.

Finding the Best Rental Location 

The city is divided into four quadrants, with Burnside Street splitting the north from the south and the river splitting the west from the east. There are tons of rental options in each of the neighborhoods. Read on below for a breakdown of Portland by neighborhood. 

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The Southwest: Downtown

When choosing Portland vacation rentals, downtown is the best place to be for many tourists; it’s the most centralized location and is close to numerous major attractions. This is handy if you don’t have a car. In this commercial area, shop for international brands at tax-free prices and dine out in the many restaurants or at the food trucks. Downtown is just below Burnside Street, which is home to the city’s legendary bookstore called Powell’s City of Books. You actually need a map to find your way around the world’s largest independent bookstore.

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longside the river, wander in the Tom McCall Waterfront Park admiring its fountains and sculptures. A trip to the Portland Saturday Market, located at the top of the park, is a must. This arts and crafts market is an ideal place to find souvenirs and try ethnic foods.

Favorite local spots: Start your day with a great cup of coffee at Good Coffee. For dinner, enjoy a tasty plate of Agnolotti stuffed with beef and cabbage at Mucca Osteria. And find a nightcap at the Teardrop Lounge. We love to recommend a House of Balloons, a blend of vodka, Aperol, and citrus.

Where to stay downtown: Find a great hotel or condo in the downtown scene. There are some small single-family homes as well, but you won’t be at your place too much if you stay here. We’d suggest finding something with the basics, so most of your budget can go towards all there is to do downtown.

The Northwest: The Pearl District, Nob Hill, and St. John’s

The Pearl District is a walkable area in a central location to the north of downtown. Wander around art galleries, shop in boutiques, and admire the architecture during the day, including the historic Steel Bridge that crosses the Willamette River. At night, the area comes alive with eateries, brewpubs, and wine bars. The Pearl District borders Chinatown and, when you’ve entered through the Chinatown Gate, you’ll find a number of restaurants and grocery stores. A visit to the tranquil Portland Classical Chinese Garden is a must.


Trendy Nob Hill has the ambiance of a small village and is filled with boutique shops, wine bars, and cafés. Known as the “alphabet district,” its tree-lined streets showcase Victorian buildings from the 19th century. The charming neighborhood of St. John’s is a quieter place to stay. When looking for vacation rentals in Portland, Oregon, Nob Hill is only recommended if you have a car, as the area is further afield than the other neighborhoods. Visit the historical Cathedral Park while you’re there.

Favorite local spots: Check out Sisters Coffee for a tasty, caffeinated beverage. Next, get over to Andina for some mouthwatering lamb terrine (gluten-free). And finally, enjoy a perfectly prepared libation from the Vault Cocktail Lounge. We think you’ll love the Check Mate, a decadent blend of rum, coconut, and anise. 

Where to stay in the Northwest: These iconic Portlandian neighborhoods are a bit more residential, which means that finding a cute rambler at a great price here is not a challenge at all. Look for great deals on these homes during the winter season.

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The Southeast: Central Eastside, Hawthorne, and Division

The coffee culture of Portland is definitely set in Central Eastside. Enjoy your coffee in waterfront establishments or those that feature artistic surroundings. The numerous bars and restaurants make Central Eastside a lively place to go at night. Vintage is the theme in Hawthorne, with its vintage theaters and shops. This laid-back area has inexpensive eateries, music stores and boutiques. Search through the antiques at Sellwood Antiques Mall.

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Foodies will love Division, which is filled with food cart pods and some of the most popular restaurants in Portland. Quench your thirst in the coffee and tea shops or with beer at some of the popular bars.

Favorite local spots: Start the day off on the right foot with a cup of something tasty at Stumptown Roasters. Grab a healthy and delicious bowl at Feel Good. Try the Painted Hills Bowl with avocado, broccoli, and shaved radish for something light. And when you’re ready for a nightcap, be sure to check out Deadshot.  

Where to stay in the Southeast: Find a great condo on Division Street to the south or Glisan to the north. We’d also suggest looking around the Willamette River for some amazing views. 

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The Northeast: Alberta Arts District and Mississippi Avenue

Culture vultures can get their fix in Alberta Arts District. It’s filled with galleries, boutiques, bars, and eateries. If part of your vacation falls on the last Thursday of the month, don’t miss the free art walk that’s aptly named Last Thursday and covers 15 blocks.

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The hip neighborhood of Mississippi Avenue is unconventional compared with Portland’s other neighborhoods. It has quirky shops, such as the ethical taxidermy shop called Paxton Gate and an emporium for Portland’s alternative media called Reading Frenzy. Listen to live music at Mississippi Studios, which you’ll find in a renovated church.

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Your Portland vacation will be that much more enjoyable when you can do it while saving money. You might even be surprised at how much you can see and do without excessive spending.

Favorite local spots: For the coffee-lovers, try the roasted goodness at Saint Simon Coffee Company. From there, make sure you grab lunch and dinner at Cliff’s. Start with a shrimp cocktail and then get into one of their famous burgers. The cocktails at Cliff’s are legendary in their own right, but we think you might also want to check out Wonderly. Try an Oil Washed Martinez or any of the marvelous creations the bartenders have come up with.

Where to stay in the Northeast: There are tons of great studios in this area. If you’re traveling with your four-legged friend, check out some of the tiny houses that are rented here, too. 

Book Your Portland Trip Today

Incredible neighborhoods, amazing food, and tons of attractions await you and your travel companions in Portland. Check out this article for even more ideas on things to do in this city.