Sip, Stay, and Explore: 5 Incredible Rentals in Willamette Valley
Picture this: You're sipping a glass of world-class Pinot Noir on a private terrace, watching the sun dip behind rolling vineyards brushed in gold. Sounds like perfection? That’s the Willamette Valley in a nutshell, and it’s far too special for just a day trip.
From cozy hideaways to luxurious estates, we’ve uncorked five of the region’s most unforgettable vacation rentals to elevate your next Oregon wine country escape.
Dundee Landing
Forget stuffy hotels—this is where your Willamette Valley adventures should begin. Dundee Landing is like that friend who knows all the best wineries, has an amazing house for parties, and makes sure you have way more fun than you planned.
When you book a stay here, you and nine friends can wake up in a gorgeous four-bedroom pad surrounded by vineyards. Start your morning with coffee on the terrace as the sun burns off the valley mist. Later, take a private wine tour guide (yeah, that’s a thing here) to hidden gem wineries, like Hyland Estate and Day Wines. Come evening, you can all gather around the fire pit to chat about which pinot was the day’s winner while the stars come out.
The house itself gets everything right, from outdoor entertainment areas to plenty of quiet spots to sneak away when you need some alone time. And the location? You’re minutes away from legendary tasting rooms but tucked away enough to feel like you’ve got wine country all to yourself.
Hidden Haven
True to its name, Hidden Haven is a peaceful, tucked-away spot in wine country ready to serve as your very own private escape. Set in the Laurelwood area of the Chehalem Mountains, this stylish three-bedroom retreat has room for six guests. And it’s equipped with all the cozy comforts you need to relax, recharge, and sip your way through the valley.
At this rental, you’re just minutes from some of the Willamette Valley’s most iconic Pinot Noir vineyards, but honestly? Once you arrive, you might not want to leave. Each bedroom is warm and inviting, offering plenty of space to rest and recharge. The main suite steals the show, though, with a deep soaking tub that practically begs for a slow, relaxing soak.
There’s even more to enjoy here, too. If you’re in the mood for a cozy night in, settle into the private media room for a movie. Or take your glass out to the covered deck, where a built-in fireplace sets the stage for long conversations under the stars. Prefer something quieter? Curl up by the wood-burning fireplace with a book and let the hours slip by.
The Pearl
Tucked into the heart of Newberg, The Pearl is a charming 1920s craftsman where vintage character meets modern comfort. And it’s absolutely enormous, with over 3,700 square feet of space for nine guests to spread out, settle in, and make the most of wine country. As a bonus, the yard’s fully fenced, so your four-legged travel buddy is welcome, too.
Every corner of this home is built for relaxing. Chill by the fireplace with a board game and a glass of your favorite wine. Kick back for a movie night in the cozy finished basement. Or settle into the porch swing and let the small-town quiet wash over you. If you’re planning group dinners, there’s a full kitchen ready for action and a dining table that seats ten, perfect for pairing your favorite local bottles with a home-cooked meal.
When it’s time to call it a night, hotel-style mattresses with soft bedding ensure every guest gets their own little slice of luxury. The plush robes and locally made soaps are a nice touch, too. Want to feel even more spoiled? Explore the valley without lifting a finger by calling Pinot Car Wine Tours for a custom wine-tasting experience.
Pearl of the Valley
Most wine country rentals scream "stock photos" louder than a corkscrew pop. But not this place. Pearl of the Valley is where your crew's Instagram stories write themselves. It’s a three-bedroom beauty sitting right in the sweet spot of the Willamette Valley, ready to be your home base for Oregon wine adventures.
Upon landing here, the kitchen will undoubtedly catch your eye first. And you can bet that the big marble island will be where everyone hangs out. Morning coffee planning sessions, afternoon cheese boards with local finds, evening wine tastings with your day's discoveries… It all happens here.
After a full day of wineries, you'll fall in love with the bedrooms, too. It’s all super comfy beds, nice sheets, and the kind of quiet you can only get away from city life.
Even practical stuff gets the VIP treatment here. Need to send a quick work email? The office space has you covered. Electric vehicle? There's a charging station waiting. Want to spend the evening stargazing with a glass of something local? Step outside and thank yourself for booking this place.
Avery House
Most vacation rentals say they have space, but the Avery House actually delivers. This beautiful, brand-new craftsman home has room for up to 12 guests and feels more like your own private wine country resort than just another vacation rental in Willamette Valley.
With three spacious levels, it’s designed to bring people together and give everyone a little room to breathe. The main floor features high ceilings, a cozy gas fireplace, and an open layout that keeps everyone connected, so even the cook doesn’t miss out on the wine talk happening in the living room.
The sleeping situation? Next level. Four spacious upstairs bedrooms include a jaw-dropping primary king suite with its own wet bar (midnight nightcap, anyone?). The bathroom feels lifted from a luxury spa magazine, giving you the perfect place to soak away a tough day of wine tasting.
But the lower level steals the show. Aptly nicknamed "the fun zone,” it’s where the real vacation magic happens, with a game room that's witnessed countless friendly competitions and grudge matches. Need a breather? Step outside to the fire pit where ghost stories and wine stories flow equally freely under the stars.
Find a Charming Willamette Valley Rental
The real magic of wine country shows up after sunset, when the tastings wind down and you head back to a beautiful place you can call your own. From the stylish rooms at The Pearl to the sweeping vineyard views at Dundee Landing, each of these rentals gives you a special way to enjoy the Willamette Valley.
Our local partners picked them to help make your whole trip feel amazing, not just give you a place to crash. Book your stay and see the valley the way locals do, one relaxing moment (and glass of Pinot) at a time.
