Oregon Vacation Rentals
Soak up the diverse landscapes of Oregon from the comfort of our luxury Oregon vacation rentals, equipped with hot tubs and more.
About our Oregon vacation rentals
Whether you're planning to experience the mountainous great outdoors, or soak up some classic R and R along the dramatic coastline, our luxury vacation rentals in Oregon invite you to experience the most exhilarating side of this beautiful state.
Choose from woodland cabins with hot tubs perfect for fun group getaways, or scenic balcony retreats and ocean-view retreats, for taking things easy. Enjoy a hassle-free year-round vacation, with fully-equipped kitchen diners, cozy fireplaces and fire pits, alongside BBQs, garden games and more to effortlessly help optimize your seasonal break.
Tourists come to Oregon for its breathtaking landscapes, where rugged coastlines, towering mountains, and lush forests create the perfect playground for outdoor enthusiasts. Whether it's exploring the dramatic beaches along the Pacific, hiking around shimmering lakes and glaciers, or taking a scenic drive through pristine highways, Oregon offers adventure at every turn. Its vibrant cities, like Portland and Bend, provide a mix of arts, culture, and world-class dining, while historic small towns offer a glimpse into the state’s rich heritage.
Oregon is ideal for all types of travelers, from couples seeking romantic retreats in cozy coastal inns or vineyard stays in the Willamette Valley to families enjoying interactive museums, waterfalls, and wildlife encounters. Groups can find excitement in outdoor adventures like whitewater rafting, skiing on Mount Hood, or exploring the Crater Lake National Park.
Whether you're looking for relaxation or adrenaline-fueled exploration, Oregon's diverse landscapes and welcoming communities make it a must-visit destination year-round.
The best time to visit Oregon depends on the experience you’re looking for, as each season offers something unique.
Spring (March–May)
With temperatures ranging from 50–65°F (10–18°C), spring brings lush greenery, blooming wildflowers, and rushing waterfalls. It’s a great time to explore Oregon’s state parks, including Silver Falls and the Columbia River Gorge.
Summer (June–August)
Warm and dry, with temperatures between 70–90°F (21–32°C) inland and 60–70°F (15–21°C) on the coast, summer is perfect for beach trips to places like Rockaway Beach, as well as hiking, and outdoor adventures. The Oregon Coast shines with tide pooling, whale watching, and scenic drives along Highway 101.
Fall (September–November)
Crisp air and vibrant foliage make autumn a stunning time to visit, with temperatures ranging from 45–75°F (7–24°C). It’s ideal for wine tasting in the Willamette Valley, hiking in Crater Lake National Park, and enjoying fall festivals.
Winter (December–February)
With temperatures between 30–50°F (-1–10°C) inland and 40–50°F (4–10°C) on the coast, winter is great for skiing in the Cascades and storm watching along the rugged coastline. Cozy towns like Bend and Hood River offer snow sports and craft breweries for a perfect winter retreat.
The best part of Oregon to visit depends on your interests, whether you’re looking for outdoor adventures, scenic coastlines, or vibrant city life.
Oregon Coast
Stretching over 360 miles, the coastline is perfect for beach lovers, offering stunning views, tide pools, whale watching, and charming seaside towns like Cannon Beach, Rockaway Beach and Newport. The famous Highway 101 drive showcases rugged cliffs, lighthouses, and picturesque ocean vistas.
Portland & the Willamette Valley
Portland is a must-visit for foodies, craft beer lovers, and those who enjoy quirky urban culture, with lush parks and gardens throughout the city. Nearby, the Willamette Valley is Oregon’s premier wine country, offering scenic vineyard tours and award-winning Pinot Noir.
Columbia River Gorge & Mount Hood
This region is a paradise for hikers and waterfall chasers, with iconic spots like Multnomah Falls and scenic drives along the Historic Columbia River Highway. Mount Hood offers year-round outdoor activities, including skiing in winter and alpine lake hikes in summer.
Central Oregon (Bend & Smith Rock)
Outdoor enthusiasts will love Bend, known for its high desert scenery, craft breweries, and proximity to Smith Rock’s world-class rock climbing. Sunriver and the Deschutes River provide excellent kayaking, mountain biking, and winter skiing at Mt. Bachelor.
Southern Oregon & Crater Lake
Home to the breathtaking Crater Lake National Park, this area is perfect for nature lovers looking to explore the deepest lake in the U.S. The nearby Rogue River offers excellent whitewater rafting, and Ashland is famous for its Shakespeare Festival.
Eastern Oregon (Painted Hills & Wallowas)
For off-the-beaten-path exploration, the Painted Hills showcase surreal, colorful landscapes, while the Wallowa Mountains, known as the “Alps of Oregon,” offer stunning alpine scenery and hiking. This region is remote but rewarding for those who love untouched wilderness.
Best time to visit Oregon
The best time to visit Oregon is May to September, when the state experiences its driest and most comfortable weather. During these months, long daylight hours and mild to warm temperatures make it ideal for exploring Oregon’s diverse scenery, from the dramatic Oregon Coast and volcanic landscapes of Crater Lake to the vibrant city life of Portland and the lakes and forests of Central Oregon.
Late spring and early autumn are particularly appealing, offering beautiful scenery, fewer crowds, and a relaxed pace, while summer is perfect for outdoor adventures, scenic drives, and enjoying Oregon’s natural beauty at its peak.
Food and drink in Oregon
Food and drink in Oregon are defined by fresh, local ingredients and a strong farm-to-table culture. The state is known for its Pacific Northwest seafood, including Dungeness crab, salmon, oysters, and halibut, often served simply to highlight their natural flavours.
Oregon is also famous for its wine regions, particularly the Willamette Valley, renowned for world-class Pinot Noir, as well as excellent craft beers and artisanal spirits found throughout the state. In cities like Portland, creative dining scenes blend global influences with local produce, offering everything from casual food carts to refined dining experiences.
From coastal seafood restaurants to vineyard tastings and mountain lodges, food and drink in Oregon reflect the state’s relaxed lifestyle and deep connection to its landscapes.
Flying to Oregon is easiest via Portland International Airport (PDX), the state’s main gateway. From PDX, it’s around 20–30 minutes to downtown Portland, 1.5–2 hours to the Oregon Coast, 3 hours to Bend, and about 4 hours to Crater Lake National Park by car.
Regional airports such as Eugene (EUG), Redmond/Bend (RDM), and Medford (MFR) offer convenient access to southern and central Oregon, reducing driving times to nearby mountain, lake, and wine-country destinations.
Driving in Oregon is one of the best ways to explore the state’s varied landscapes. Roads are well maintained, clearly signposted, and often scenic, especially along the Oregon Coast, through the Willamette Valley, and across Central Oregon.
Drivers travel on the right-hand side of the road, and distances between destinations can be long, making a rental car highly recommended. Speed limits are enforced, and weather conditions can change quickly in mountain and coastal areas, particularly in winter. Overall, driving in Oregon offers freedom, flexibility, and access to some of the state’s most beautiful scenery.
Trains in Oregon offer a comfortable way to travel between some of the state’s main cities. Amtrak services connect destinations such as Portland, Salem, Eugene, Albany, and extend north to Seattle and south toward California.
Train travel is ideal for relaxed, scenic journeys and city-to-city trips, especially if you’re staying in urban areas. However, train routes are limited and do not reach many of Oregon’s coastal, mountain, or rural destinations, so rail travel is best combined with car hire for exploring the state more fully.
Explore Crater Lake National ParkHome to the deepest lake in the U.S., Crater Lake stuns with its vivid blue waters, scenic hiking trails, and boat tours to Wizard Island. In winter, the park transforms into a snowy wonderland perfect for cross-country skiing and snowshoeing.
Adventure on Mount HoodOregon’s tallest peak offers year-round fun, from skiing and snowboarding at Timberline Lodge to summer hiking and alpine lake exploration. Enjoy the views from the Hood Scenic Byway, or go fruit picking in the Hood River Valley.
Hike & Climb at Smith Rock State ParkThis high-desert gem is a world-class rock climbing destination, with stunning red rock formations and miles of scenic hiking trails. The Misery Ridge Trail rewards hikers with panoramic views of the Crooked River.
Explore the Oregon CoastThe rugged coastline is ideal for exploring tide pools, spotting whales, and strolling along scenic beaches like Cannon Beach and Pacific City. Drive along Highway 101 drive and soak up epic vistas, lighthouses, and quaint seaside towns.
Raft & Kayak the Deschutes RiverThe Deschutes River is a paradise for whitewater rafting, kayaking, and fly fishing. The river also features scenic floating routes, making it a relaxing way to take in Oregon’s breathtaking high desert landscapes.
Visit the Willamette Valley Wine CountryAs one of the top Pinot Noir-producing regions in the world, the Willamette Valley is a must-visit for wine lovers. Rolling vineyards, charming tasting rooms, and farm-to-table dining make it a perfect destination!
Discover the Columbia River Gorge & Visit Multnomah FallsThe Historic Columbia River Highway offers a scenic drive through lush landscapes, perfect for hiking. Discover endless waterfalls, including the iconic Multnomah Falls, where visitors can hike up to the scenic Benson Bridge.
Oregon Concierge Services
Take your Oregon vacation to new heights of convenience and comfort, with our optional Concierge Services. From car hire, groceries, BBQ packs and babysitting to family equipment rental, boat hire, guided tours, private chefs and more, however your dream getaway in Oregon looks, Top Villas is here to make it a reality.
Oregon Vacation Rentals with Hot tub
Whether you're exploring the nature trails or sandy shores, our collection of Oregon vacation rentals with hot tub or pool invite you to do so in style. Start the day with a refreshing dip in your pool, for a spa-style experience in the privacy of your vacation home. After an action-packed day exploring, enjoy a tempting soak in your scenic private hot tub.
Take in the sunset and switch on to full vacation mode, with your family and friends. Accompanied by firepits, BBQs, private outdoor space and all-weather games, unforgettable reunions are made with a Top Villas stay.
Beachfront vacation rentals in Oregon
Discover beachfront vacation rentals in Oregon, Arch Cape and Cannon Beach, where the dramatic Pacific Ocean is the main attraction. Arch Cape offers a peaceful, secluded shoreline, while Cannon Beach is famous for Haystack Rock, its art scene, and charming coastal village.
These rentals are designed to maximise the stunning sea views, with direct beach access and the sound of the surf as your daily backdrop, perfect for sunrise walks, sunset moments, and a truly coastal escape.
Pet friendly rentals in Oregon
Explore Oregon with your furry companion in comfort and style with our pet-friendly rentals in Oregon. Whether you’re drawn to the wild beauty of the Oregon Coast, the forests of the Cascades, or the rolling landscapes of the Willamette Valley, we offer a selection of homes where pets are warmly welcomed.
These pet-friendly rentals provide easy access to scenic trails, parks, beaches, and outdoor adventures, ideal for hikes, beach runs, and long walks through nature. Many properties include fenced yards or nearby open spaces, making it simple to enjoy quality time with your dog in Oregon’s fresh air.
Perfect for couples, families, and groups who want to bring their pets along, our pet-friendly rentals in Oregon combine relaxed comfort with access to some of the state’s most beautiful settings.
