Oregon has a way of making the holidays feel both cozy and adventurous at the same time. The mix of mountain towns, river valleys, and scenic coastlines gives you endless ways to celebrate the season. Whether you picture yourself skiing on fresh powder, sipping local wine by a fire, or walking through a snow-dusted forest, Oregon makes it all possible. And with Arrived, finding the perfect place to stay in the heart of it all is simple. Our vacation rentals across Bend, Sunriver, Hood River, Eagle Crest, and Redmond combine space, comfort, and convenience for a holiday getaway to Oregon that feels just right.
Bend
Bend turns into a winter playground when the holidays arrive. The Cascade Mountains provide a stunning backdrop for everything from skiing to shopping. Mt. Bachelor is the main draw for snow lovers, offering one of the best ski resorts in the Pacific Northwest. Whether you’re a skier, snowboarder, or just love the atmosphere of a mountain lodge, it’s the kind of place that makes you feel alive in the fresh winter air.
Downtown Bend feels like a postcard during the holidays. The lights, the local shops, and the small-town warmth make it easy to spend hours wandering. Grab a hot coffee, browse local boutiques, and stop by a brewery or two to sample some of Oregon’s best craft beer.
Bend also shines for outdoor lovers beyond the slopes. You can snowshoe through the Deschutes National Forest, take a scenic drive along the Cascade Lakes Highway, or enjoy a calm morning walk along the Deschutes River Trail. The area is filled with hot springs that make for a perfect post-adventure soak. Those visiting later in the winter can also explore the High Desert Museum, which blends art, history, and wildlife into one beautiful experience.
Our Bend vacation rentals make it easy to relax after a day out exploring. Choose from charming cabins or larger mountain homes with fireplaces, private hot tubs, and beautiful forest views. Each property is fully equipped with modern kitchens and comfortable living spaces, perfect for a holiday dinner or movie night by the fire. Whether you want to be close to the slopes or tucked away in a quiet wooded setting, Bend offers the kind of versatility that makes the holidays exactly what you want them to be.
Sunriver
If your idea of the perfect holiday includes peace, quiet, and a little outdoor adventure, Sunriver is the place to be. Located just south of Bend, this resort community is designed for rest and recreation. During winter, it becomes a hub for skiing, snowshoeing, and sledding, while in the warmer months, you can explore miles of bike paths, hiking trails, and the nearby Deschutes River.
Sunriver’s holiday season feels like something out of a storybook. The town is blanketed in snow, the Village at Sunriver is lit up with festive lights, and the air always smells like pine. You can start your mornings with coffee and mountain views, spend your afternoons at Mt. Bachelor, and your evenings soaking in a hot tub under the stars. The calm atmosphere makes it a perfect spot for families and couples alike who want to slow down and enjoy the beauty of the season.
Beyond the obvious winter activities, Sunriver has a variety of local experiences that make the holidays memorable. You can take a sleigh ride through the woods, go ice skating in the village, or visit local craft fairs for handmade gifts. When hunger strikes, grab dinner at one of Sunriver’s local restaurants that specialize in farm-to-table cuisine and warm comfort food. For those who want to explore a bit more, a short drive to Lava Lands or the Oregon Observatory adds something educational and unique to your holiday plans.
Arrived offers a variety of Sunriver vacation rentals ranging from intimate condos to spacious family homes. Many feature open floor plans, fireplaces, and outdoor decks that make it easy to settle in for the season. Whether you’re planning a quiet getaway or bringing the whole family, these homes have everything you need to make your holiday special. The combination of natural beauty and home-like comfort makes Sunriver a favorite year after year for travelers seeking something peaceful yet full of possibility.
Hood River
For travelers who love a mix of adventure, charm, and local flavor, Hood River is a dream holiday destination. This picturesque town sits along the Columbia River Gorge and offers incredible scenery year-round. In the winter, it’s known for skiing at Mt. Hood Meadows and snowshoeing through peaceful forest trails. In the warmer months, the river becomes a playground for paddleboarding, fishing, and windsurfing.
Hood River also comes alive with seasonal cheer during the holidays. The downtown area glows with lights, the shops are filled with handmade goods, and local wineries and breweries host festive tastings. You can visit nearby fruit farms that turn into winter markets, or take a drive along the famous Fruit Loop to see the snow-covered orchards. It’s one of those places that balances small-town friendliness with a sophisticated edge, thanks to its thriving art scene and locally owned restaurants.
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If you love exploring, Hood River gives you endless options. Take a walk along the waterfront, stop into a café for a pastry and warm cider, or make your way to the Columbia River Gorge National Scenic Area for a breathtaking winter hike. The views of frozen waterfalls and misty canyons are worth the trip alone. At night, the lights reflecting off the river create a peaceful scene that feels straight out of a painting.
Our Hood River rentals give you the perfect base for exploring the area. Each home combines comfort with Oregon style, featuring spacious living rooms, fireplaces, and fully equipped kitchens. Many also include decks or patios overlooking the river or surrounding mountains. It’s the kind of setting where you can pour a glass of local wine, put your feet up, and simply enjoy being there. From cozy cottages to modern lodges, Arrived’s Hood River properties let you experience this stunning region exactly the way locals do – comfortably, quietly, and surrounded by beauty.
Eagle Crest
Eagle Crest is one of those places that feels made for the holidays. Located near Redmond, this resort community is surrounded by high desert scenery and offers easy access to Central Oregon’s best attractions. During the winter, you can ski at Mt. Bachelor, explore Smith Rock State Park, or enjoy sleigh rides through snowy trails. When the sun is out, there are golf courses, nature trails, and spa facilities for those who want a slower pace.
The holidays in Eagle Crest have a laid-back rhythm. You can spend your mornings on the trails, your afternoons by the fire, and your evenings gathered around the dinner table. The resort’s amenities make it a perfect spot for families or couples looking for both activity and relaxation. It’s also a convenient choice for visitors who want access to everything Central Oregon offers but prefer a quiet retreat away from busier areas.
Beyond the resort, there’s plenty to see and do nearby. Visit local breweries in Redmond, take a day trip to Sisters for shopping and galleries, or explore the Cline Falls State Scenic Viewpoint for beautiful river views. Eagle Crest also offers horseback riding, indoor and outdoor pools, and fitness centers, making it easy to stay active while still embracing the slower holiday pace.
Arrived offers luxury vacation homes and townhomes in Eagle Crest that make it easy to enjoy your stay. Expect modern furnishings, large windows with beautiful views, and cozy fireplaces that set the tone for a relaxing getaway. Many rentals feature private hot tubs, perfect for warming up after a chilly evening walk. Whether you want to play, relax, or simply recharge, Eagle Crest offers the kind of space where holiday memories come naturally.
Redmond
Redmond is the heart of Central Oregon, offering a friendly small-town feel with easy access to everything the region has to offer. The holidays bring a mix of outdoor adventure and local charm. You can visit Smith Rock State Park for breathtaking winter hikes, explore nearby caves, or head into town for local shopping and dining. The Redmond Christmas Parade and Tree Lighting are community favorites, filling the streets with lights, music, and laughter.
Redmond’s local restaurants and cafés take on an especially cozy feel during the holidays. You can warm up with a hot cup of coffee, sample craft beer at a local brewery, or enjoy a holiday meal at one of the farm-to-table restaurants that highlight the best of Oregon’s local ingredients. The town’s small boutiques and markets are also great spots to pick up unique gifts and handmade goods from local artisans.
This city is a great choice for visitors who want to be close to both Bend and Eagle Crest while enjoying their own space. Redmond’s central location means you can easily explore all of Central Oregon’s highlights, from mountain trails to local vineyards. The nearby airport also makes it a convenient destination for travelers flying in for a quick winter escape.
Our Redmond vacation rentals offer everything you need for a comfortable and festive stay. Each home is designed with relaxation in mind, featuring open layouts, fully stocked kitchens, and inviting living areas. Many properties have outdoor patios with views of the high desert and mountains beyond. Whether you’re planning a quiet holiday or a family celebration, Redmond delivers the perfect balance of comfort and convenience. And with Arrived’s attention to detail, every stay feels seamless from start to finish.
Celebrate the Holidays with Arrived
No matter which Oregon destination you choose, staying with Arrived ensures your holiday is comfortable, memorable, and completely stress-free. Our vacation rentals give you the space and freedom to celebrate however you like. Cook family dinners in a fully equipped kitchen, gather by the fire for a movie night, or relax outside and take in the view.
Each property is carefully selected for its quality, location, and amenities, so you can focus on what matters most: spending time with the people you love. Whether you prefer mountain views in Bend, quiet luxury in Sunriver, or riverfront charm in Hood River, you’ll find a home that feels just right for your holiday.
Book Your Oregon Holiday Getaway Today
An Oregon holiday getaway offers the perfect mix of scenery, adventure, and holiday spirit. From the snow-covered slopes to the cozy small towns, it’s a place that makes every season feel special. Let Arrived help you make it unforgettable. Browse our vacation rentals across Bend, Sunriver, Hood River, Eagle Crest, and Redmond, and find the one that fits your holiday plans. Book your Oregon getaway with Arrived today and start planning the perfect holiday escape!
