Holiday rentals in Willamette Valley

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Top-rated holiday rentals in Willamette Valley

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in Salem

4.97 out of 5 average rating, 295 reviews

The Vineyard House - Cozy & Modern

Welcome to our charming cottage, nestled amidst a picturesque Pinot Noir vineyard in the renowned Willamette Valley, voted the next Napa Valley by Time Magazine. This serene retreat offers a truly unique experience for wine enthusiasts and nature lovers alike. Whether you're here for a romantic getaway, a wine-tasting adventure, or simply seeking a peaceful escape you won't be disappointed. With heated floors and a real wood burning fire place, you can cozy up during these months in tranquility.

Top guest favourite

Guest house in Dayton

5 out of 5 average rating, 196 reviews

Modern Farmhouse - Country living in wine country.

Escape to Oregon Wine Country! Light and bright modern farmhouse style rental . Enjoy a private suite in a detached barn with views of a country setting. King size bed with large Master suite and private patio. Queen size bed in a beautiful 2nd bedroom. Rental has a separate entrance in its own building. A 1800sf family/ rec room. Cozy fireplace, full kitchen, washer and dryer. Outdoor dining table on the patio. Located just one mile from Stoller Family & many more. Owners on site to assist

Top guest favourite

Home in Newberg

4.96 out of 5 average rating, 251 reviews

Luxury Wine Country Estate

Welcome to Luxury Wine Country Estate, an oasis where luxurious refinement meets the epitome of wine country indulgence. Revel in unmatched hositality, thoughtfully designed to include Tempur-Pedic suites, therapeutic hot tub, rejuvenating sauna, invigorating cold plunge, and the most stunning valley and vineyard views. Every touch is meticulously crafted, from heated stone floors and Dyson innovations to dual gourmet kitchens, Yeti picnic essentials, EV charging capabilities, and so much more.

Guest favourite

Earthen home in Salem

4.98 out of 5 average rating, 319 reviews

The Bag Inn A Hobbit Home

The Bag Inn is a Hobbit Style Home. Filled with comfort and wonder, it will help you step out of the mundane world and retreat to a fantasy world. The Bag Inn features a fire place, walk in shower, and soaker tub. It is 1000 sq ft complete with separate bedroom, large luxurious bath, living and dining space. It sits on 2.5 acres to give you the feel of being out in the country while being only minutes from town. This is a guest home. For more information please read full listing details.

Guest favourite

Home in McMinnville

4.98 out of 5 average rating, 244 reviews

Wine Country Escape | Walk to Downtown 3rd Street

Escape to the land of plenty! This beautiful modern home is a short 5 minute walk from all the offerings of the popular downtown 3rd street in McMinnville! It doesn't get closer or cozier than this. Downtown McMinnville has over 20 tasting rooms you can walk to. You can also explore 250 wineries and vineyards within 20 miles of the house! Come visit and find your new favorite pinot noir, craft beer, locally roasted coffee and foods. Come discover the bounty Oregon wine country has to offer!

Top guest favourite

Guest house in Stayton

5 out of 5 average rating, 565 reviews

Spoil yourself! Luxury Cabin on the Santiam River

Escape to our Luxury Cabin Suite, designed just for two adults, located right on the beautiful Santiam River—only 20 minutes from Salem! Whether you’re looking for a peaceful place to relax, a romantic getaway, or simply a spot to unwind, you’ll find it here… and best of all, no dishes to wash! Love the outdoors? Bring your hiking boots, fishing gear, kayak, or raft and make the most of the surroundings. Please note: Our cabin features one bed and is not suitable or equipped for children.

Superhost

Guest suite in Dundee

4.9 out of 5 average rating, 401 reviews

Valley Views w. Hot Tub

Enjoy panoramic views of wine country. Tasting rooms and amazing restaurants all close. Harvey Creek Trail is steps away. High end furniture and finishes Custom and modern, yet cozy decor 2 full King Master Suites with luxury tiled baths, oversized walk-in rain showers. Hot tub on your own large, covered and private deck overlooking the valley. Electronic front door lock-Easy Check in. Washer/Dryer Private, separate accommodations Parking for 2 tandem parked vehicles in drive

Top guest favourite

Tiny home in Newberg

5 out of 5 average rating, 685 reviews

Garden Spa Getaway in Wine Country-Newberg

Enjoy the hot tub and sauna for relaxation! The Tiny Home is privately tucked in a garden oasis, in a quiet residential neighborhood. Only 13 blocks to downtown Newberg 's lovely wine boutiques and restaurants, 6 blocks to George Fox University, 45 min. from PDX Airport. Spacious and comfortable with 192 sq. feet modern atmosphere. Complimentary specialty cheese & oatmeal cups for breakfast. Nice bikes to tour beautiful Newberg and local wine boutiques. *Two night minimum stay.

Top guest favourite

Loft in Dundee

4.95 out of 5 average rating, 876 reviews

Luxury Wine Country Studio at the Market Lofts

Steps away from world class tasting rooms & directly above local hotspot, Red Hills Market, our loft is located in the center of it all. Decorated with a blend of rustic wine country and industrial modern elements, our great room style studio, includes a living room area with a sleeper sofa. Measuring 600+ square feet, it is quite spacious and comfortable. Residing above Red Hills Market adds to the appeal & offers endless opportunities for fun...wood fired pizza, wine & more!

Top guest favourite

Home in McMinnville

4.97 out of 5 average rating, 271 reviews

Chef’s Kitchen + Firepit | Single Level Home

★★★★★ “Amazing kitchen, great backyard, and fantastic location.” Welcome to your McMinnville midcentury retreat—a designer home in the heart of McMinnville. After a day of vineyard tastings, cook in the chef’s kitchen, sip Pinot under bistro lights, and gather by the firepit beneath the stars. This isn’t just a place to stay. It’s a tribute to Oregon’s original winemakers and the playful, relaxed spirit of the Valley.

Top guest favourite

Guest house in Salem

4.97 out of 5 average rating, 336 reviews

Willamette Valley Chateau

ESCAPE! This is by far will be the best AirBnb experience you will have. This place is a piece of heaven and relaxation, which lets you enjoy the view, nature and quiet time away from the city. Great place to celebrate your anniversary with a quiet retreat, wine tasting or visit nearby nature. NO CONTACT SELF CHECK IN. You will not have contact with anyone during your stay. Super fast internet.

Top guest favourite

Flat in Newberg

4.94 out of 5 average rating, 1,006 reviews

Bright, Unique Apartment in Heart of Wine Country

*4 Min to George Fox University *10 Min walk to wine tasting rooms & restaurants *50+ wineries within 10 min drive This adorable daylight basement apartment is like walking into a storybook oasis. You’ll love the forest views from the floor to ceiling windows. Enjoy your morning coffee (or evening wine) from the private seating area and take in the sounds of chirping birds and babbling brook.