Holiday rentals in Willamette Valley

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Top-rated holiday rentals in Willamette Valley

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Top guest favourite
The exterior of a two-story studio is framed by lush greenery and trees. The building features a spiral staircase leading to a private balcony with black railings. A shared garden area is visible below, with a hammock and various plants around the space.
Guest house in Portland
4.98 out of 5 average rating, 242 reviews

Spacious, bright garden studio on Peninsula Park

Explore the world-class restaurants, coffee shops and bars in the nearby Williams and Mississippi districts. Take a stroll around the award winning (and oldest) rose garden in the City of Roses across the street in Peninsula Park. At home, this second story studio has extra space in the meditation loft, a full kitchen, fast internet, and projector for streaming. Enjoy your private deck over the shared garden with hammock and H/C outdoor shower. Bus and train nearby with ample on-street parking.

Top guest favourite
A bright living space features a comfortable sofa, two armchairs, and a round coffee table, all arranged around a fireplace with decorative elements. Natural light illuminates the room, which is beautifully enhanced by green plants and elegant lighting.
Home in McMinnville
5 out of 5 average rating, 106 reviews

The Mack House - Walk Downtown

Enjoy a stylish experience at this centrally located 2-level home. Walking distance to historic downtown 3rd St & the newly developed Alpine district where you’ll find excellent restaurants, wine tasting, breweries, boutiques, coffee, antiques and more. This home is for adults only and is not furnished for children. Sleeping Space: - 1 King Bed Upstairs - 1 Queen Bed Downstairs Bathrooms: - 3/4 on Main (Shower Only) - 3/4 in Upper (Bathtub Only)

Top guest favourite
A modern living area features a light grey sectional sofa and a round coffee table placed on a textured area rug. Natural light enters through large windows, illuminating the space. A wall-mounted TV and a cozy armchair complement the inviting atmosphere, with a fireplace enhancing the comfort.
Home in Newberg
4.98 out of 5 average rating, 203 reviews

Villa Fontana: Modern, Wine-Country Comfort

Welcome! Enjoy a fresh, clean, retreat while you sip your way through Oregon's Wine Country. A modern home nestled amid local historic landmarks, you will be 6 blocks from the downtown Newberg strip and within a 5 mile radius of the closest wineries, making this home the perfect choice for accessibility. Enjoy complimentary Prosecco to toast your arrival and plan to cook meals that pair with your local wine purchases using our high-end appliances!

Guest favourite
The spacious main area features large windows that allow natural light to fill the room, highlighting the soft gray sectional sofa and a plush area rug. A stylish spiral staircase leads to the loft bedroom, while a dining table is set in the corner.
Guest house in Salem
4.96 out of 5 average rating, 567 reviews

Charming 1 bedroom loft/barn apt with hot tub

Take it easy at this unique and tranquil getaway! Nestled in the heart of the Willamette Valley, this peaceful loft is perfect for the couple looking to relax and recharge. Enjoy our local farmers markets, or a baseball game at Volcanoes Stadium. Tour our local restaurants and wineries or see what’s happening this summer with our local music scene. Visit our many hikes and trails or float our rivers and lakes - and on and on!

Top guest favourite
A cozy sleeping area is featured, with a white bed neatly arranged with patterned pillows. A vintage-style side table holds a tray with glasses and a bottle, alongside a small pot of blooming flowers. Soft light from a lamp provides a warm glow.
Home in Dundee
4.97 out of 5 average rating, 358 reviews

Modern Farmhouse | Walk to Dundee Wineries

WELCOME Tucked up among the vineyards of Dundee Hills, our modern vintage farmhouse studio offers a peaceful wine country escape just steps from world-class tasting rooms. Three exceptional wineries are a short-five minute walk away—Lange Estate Winery, Torii Mor Winery and Olenik Vineyards—making this the perfect base for a relaxed weekend of tasting. Recently rated one of the Top 10 Airbnb stays in Dundee by Trip101.

Top guest favourite
Two mini-Highlander cows are seen grazing in a grassy field, surrounded by a wooden fence and lush green bushes. A bright blue sky with fluffy white clouds creates a serene backdrop, enhancing the peaceful rural atmosphere.
Barn in Sherwood
4.97 out of 5 average rating, 210 reviews

Rustic Barn | Country Getaway

Nestled atop Parrett Mountain is our countryside barn ready for you to enjoy! Conveniently located to many vineyards, and a picturesque drive to close by cities. This space offers a fully stocked kitchen and plush bedding (1 Queen/ 1 Double). Come and slow down with our rural pace of life, unique accommodations and say hi to the mini cows. Check out our photos to imagine yourself in this peaceful paradise.

Top guest favourite
An inviting living area features floor-to-ceiling windows that offer views of the surrounding forest. Minimalist furniture includes a wooden table, lounge chairs, and a futon, creating a comfortable space to relax or entertain. Natural light enhances the cozy atmosphere.
Flat in Newberg
4.95 out of 5 average rating, 1,060 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.

Guest favourite
The modern cottage exterior features a sleek design with wooden accents. Steps lead to the entrance, framed by lush vineyard rows. A gentle slope into the vineyard can be seen alongside the structure, providing a tranquil setting amidst the surrounding nature.
Cottage in Salem
4.95 out of 5 average rating, 321 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.

Guest favourite
The charming round house, surrounded by lush greenery, features large windows and a spacious deck. Vibrant flowers and ferns adorn the garden, contributing to the serene setting. Tall trees provide shade, framing a glimpse of the expansive landscape beyond.
Dome in Amity
4.97 out of 5 average rating, 276 reviews

Round House Retreat in the Woods

This peaceful round house offers a retreat from city life. Located on over 20 acres, this property offers complete silence, relaxation, and breathtaking views of the beautiful Willamette Valley below. The design offers an open floor plan as well as the unique experience of living in the round! The house is just a few minutes from numerous wineries and restaurants in Amity and McMinnville.

Top guest favourite
An open studio space features a queen bed with decorative pillows and a cozy lounge couch. A kitchenette is visible in the background, along with a wooden table and chairs. Natural light floods in from the window, highlighting the warm wooden flooring.
Home in Newberg
4.99 out of 5 average rating, 680 reviews

Newberg Garden View Suite – Peace, Rest, Enjoy

This updated suite is a totally private unit ready to enjoy. Your own separate entrance, large deck overlooking the garden, and enough space to relax. A 10-minute walk to the center of Newberg with a country feel. In the heart of Chehalem Valley within a 10-minute drive to 50+ wineries, and many beautiful areas to explore close at hand. Designed for individuals or a couple.

Top guest favourite
Guest house in Newberg
5 out of 5 average rating, 486 reviews

Wine Country Spa House - Hot Tub/Sauna/Pool

Relax in your private guest house featuring an indoor Sauna and Marquis Spa (Hot Tub) Enjoy the pool and outdoor hot tub. Take a swing at the tee off boxes, chip around - 2 holes, explore our 10 acre property, enjoy the tranquil view of the hazelnut orchard, hay fields and mountains while you kick back, relax and fall in love with Oregon Wine Country!

Top guest favourite
The exterior of the farmhouse is showcased, featuring a white facade with a black awning above the entrance. A vibrant red chair sits on the porch, while colorful flowers and well-groomed greenery enhance the inviting atmosphere. Lavender blooms are visible in the foreground.
Cottage in McMinnville
4.94 out of 5 average rating, 252 reviews

Half-Pint Farmhouse in Downtown McMinnville

Guests can visit the beautiful Willamette Wine Country and then relax in our quaint & cozy 'Half-Pint' farmhouse that is a short stroll away from the abundant farm-to-table restaurants & world class tasting rooms on 3rd Street and The Granary District. With a Walk Score of 89, you can travel on foot and enjoy yourself!

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