Where to Stay, Sip and Shop in Portland, Oregon
As travelers hunt for destinations that mix festive spirit, local charm, and meaningful experiences, Portland, Oregon shines bright this holiday season.
The city transforms into a wonderland of twinkling lights, craft cocktails, indie markets, and cozy hotels all wrapped in that signature Portland creativity (and, of course, no sales tax!)
Whether you’re looking for a winter weekend getaway or a shopping spree with personality, here’s a holiday guide that captures the best of Portland, from where to stay, sip to where to shop small and make a big impact.
Where to Stay
Portland’s hotels are decking the halls this year with special offers and festive experiences that make the city an irresistible home base this holiday season.
Shop + Stay Portland Holiday: A new citywide initiative featuring 13 hotels across downtown Portland, offering stay-and-shop incentives through the 2025 holiday season. Created by Small Shops Big Hearts and Bricks Need Mortar, the campaign invites West Coast visitors to take advantage of Oregon’s No Sales Tax and support local retailers with each purchase.
The Ritz-Carlton, Portland: The city’s luxury landmark celebrates its first festive season with two exclusive packages. Expect elegant teas, gingerbread house decorating, and a very Portland take on holiday indulgence:
Gifts of the Rose City: With local retail perks, daily breakfast, and cocktails. Available thru January 5, 2026. This offer was created in partnership with local retailers and invites guests to discover Portland’s vibrant shopping scene and tax-free treasures this holiday season. The package includes daily breakfast for two, nightly valet parking, two cocktails, and exclusive local retail offers.
Home for the Holidays: A staycation-ready offer for Oregon and Washington residents. Available thru January 16, 2026. A special rate and nightly valet parking for Oregon and Washington residents, inviting locals to enjoy a seasonal staycation in the heart of the city.
The Duniway Portland and The Nines: Both hotels add their own sparkle with downtown views, cozy dining, and walkable access to shopping, lights, and the city’s favorite holiday markets. Both hotels are just minutes away from the Portland Art Museum (PAM) which recently underwent a $116 million dollar renovation that adds nearly 100,000 square feet of gallery, including a permanent exhibit dedicated to Black art, public space and increased accessibility.
Where to Sip
Raise a glass (or mug) to Portland’s spirited side:
Portland Holiday Brew Fest: The festival returns, spotlighting limited-edition beers and ciders from top local breweries under a festive heated tent downtown.
Pop-up holiday bars and winter cocktail lounges: Across the city, bars and cocktail lounges transform into a winter wonderland bringing merry themes, moody lighting, and spiked hot cocoa to the city’s nightlife scene.
Hey Love: Transforms into “Sleigh Love” each winter – a holiday pop-up that wraps its lush, jungle-themed bar in twinkle lights, tinsel, and tongue-in-cheek festive cheer. Run by a BIPOC and queer-led team, Hey Love serves up playful seasonal cocktails (think hot buttered rum and cranberry-mezcal spritzes) alongside cozy comfort dishes.
Straightaway Cocktails: In the heart of Hawthorne, this holiday-themed mixology class, “Craft Mixology Class: Winter Wonderland”, (thru Dec. 20, 2025) invites guests to craft and taste four festive winter cocktails, dive into the history of each style, and take home recipe cards and tools to keep the spirit alive.
Deadshot: The internationally loved pop-up “Miracle” returns to Deadshot this season. The Southeast Portland bar transforms into a full-on festive wonderland decked wall-to-wall in twinkle lights and tinsel, with cocktails served in cheeky ceramic Santa mugs. This year’s lineup features creations like Rudolph’s Replacement (vodka and crème de cacao) and Jingle Balls Nog, a creamy mix of cognac, sherry, almond milk, and nutmeg.
Where to Shop
In Portland, every gift tells a story and this year, shoppers can skip the big-box bustle and explore the core of the city’s creative nature:
Wander Holiday Markets: Where diverse artisans showcase handmade jewelry, ceramics, textiles, and treats perfect for gifting with purpose. You’ll find multiple options for every kind of maker all over the city including Scan Fair, Portland Holiday Market and more.
Local Neighborhoods: For local flair, neighborhoods like Mississippi Avenue, Alberta Arts District, and Division/Clinton offer an abundance of BIPOC- and women-owned shops think: Event Cosmetics, Bridge City Mercantile, Black Wagon, and Amrapali Boutique.
And Don’t Miss…
From the Oregon Zoo’s iconic ZooLights to the Portland Gay Men’s Chorus holiday concerts and Peacock Lane’s legendary light displays, the city is aglow with ways to celebrate. Portland invites visitors to reconnect with wonder and discover the magic that happens when creativity, community, and celebration meet.
