Holiday houses in Chehalem

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Top-rated holiday rentals in Chehalem

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

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Top Guest favourite
A tranquil outdoor space features two wooden chairs and a round table, positioned to enjoy a breathtaking sunset. The sky is adorned with vibrant purple and orange clouds, casting a serene light over the landscape below.
Home in Newberg
4.97 out of 5 average rating, 263 reviews

Parrett Mtn Estate · Hot Tub, Sauna & Valley Views

8 private acres atop Parrett Mountain — sweeping Pinot Noir vineyard & valley views, Tempur-Pedic suites & heated stone floors. The only estate in Willamette Valley with an Oregon Red Cedar sauna, cold plunge, starlit hot tub & Universal EV Charging. Two full chef's kitchens, Egyptian cotton linens, Dyson air purifiers & hair tools, 4 bedrooms, sleeps 12. Optional add-ons available: private chef, Sommelier wine tasting & concierge services. 5 min to Newberg · 30 min to Portland · 40 min to PDX.

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Top Guest favourite
Cottage in Newberg
4.97 out of 5 average rating, 184 reviews

Oxberg Lake Retreat, lake & farm view in wine ctry

A storybook oasis with lake/farm views. Enjoy morning coffee or evening wine watching lake wildlife, sheep and chickens. One loft bedroom, a full bath, large living room/kitchen. Hosts live in attached home, but you have full privacy. * 5 min to George Fox * 2 min to The Allison Inn & Spa * 50+ wineries within 10 min drive *Walk to Wolves and People or Encore for a brew, Starbucks, Mod Pizza and others at Crestview Crossing *Canoeing, catch and release fishing, fire pit, games *roll-away bed

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Top Guest favourite
A private outdoor patio is depicted, furnished with a round table and four chairs. A large red umbrella offers shade, while a gas grill and vibrant greenery enhance the tranquil setting. This area provides an inviting space for relaxation and dining.
Guest suite in Sherwood
4.98 out of 5 average rating, 133 reviews

Bacchus Fields - Oregon Wine Country Studio

Bacchus Fields is a private, quiet, studio in the gateway of Oregon’s wine country, with views of Mt. Hood and beautiful scenery. The studio has a queen bed, full kitchen, private bathroom and entrance. We offer self-check in, dedicated parking with complementary Level 2 EV charging, a private outdoor patio with seating, a gas grill and fire pit. The studio is nicely situated for short and long-term stays, visits to wine country, the coast, mountains, Portland, and surrounding communities.

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Top Guest favourite
A picturesque vineyard landscape features rows of young grapevines leading up to a charming two-story house. The property is adorned with lush greenery and trees, set against a cloudy sky that hints at a tranquil atmosphere.
Farm stay in Sherwood
4.88 out of 5 average rating, 202 reviews

Ariniello Vineyard - Private 2 Bedroom Suite

Perfect location for wine tasting and touring the beautiful Pacific NW. A unique opportunity to stay on a newly planted small vineyard in your own private suite. Enjoy your very own 1st floor living quarters. The property is also located on a small farm. You will enjoy your own entry with two private bedrooms (1 king and 1 queen), living room and private bathroom. Basic kitchen set up -NO oven. The space can easily sleep 4 (6 includes an air mattress). No smoking allowed in the suite.

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Top Guest favourite
The living room features a comfortable large sofa and an armchair, arranged around a coffee table on a patterned area rug. A flat-screen TV is mounted above a brick fireplace, and natural light filters through the window, complemented by light-colored curtains.
Guest suite in Sherwood
4.98 out of 5 average rating, 320 reviews

Sherwood Hollow- Senior discount (60+) $88/night

Welcome to Sherwood Hollow! This completely refurbished retreat is a large 1200 square foot downstairs suite in our 1960's home. This spacious area has a large living room, eat-in kitchen, and spacious bedroom. The unit is private and completely closed off from the upstairs. Our home is located just a short walk from Old Town Sherwood and beautiful Stella Olsen park. This unit is near the bottom of a hill, a bit of a climb coming up from Old Town, and the driveway is on an incline.

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Top Guest favourite
A charming home is framed by vibrant bushes of blue flowers, with a large tree providing shade in the foreground. Lush greenery surrounds the property, complementing the inviting exterior of the house under a clear blue sky.
Home in Dundee
4.93 out of 5 average rating, 248 reviews

Chateau Lesieutre atop Dundee Hills’ Highest Point

Wake up above the Willamette Valley, surrounded by Oregon’s most celebrated wineries. Located at the highest point in Dundee, this serene retreat offers exquisite views. Sip your morning coffee on the terrace, enjoying the fresh country air and feeling as though you’re floating above the hills. With more than 10 wineries within two miles, it’s an ideal base for exploring wine country. After a day out, return home to unwind with evening stargazing in the courtyard or on the terrace.

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Top Guest favourite
A spacious outdoor deck features a white Adirondack chair overlooking a vast landscape. The view encompasses rolling hills and a horizon that fades into the distance under a clear sky. Hues of autumn are visible in the trees and ground, adding color to the scenery.
Home in Newberg
4.95 out of 5 average rating, 222 reviews

Spectacular Valley View in Wine Country

Relax and enjoy the best of what Oregon Wine country has to offer in our newly renovated country home. With a stunning view overlooking the Willamette Valley, you are close to over 300 wineries and tasting rooms, local craft beer, and a great social atmosphere in our small town. Enjoy soaking in the hot tub or having dinner outside under the gazebo. Have your pets outside, worry free with a large fenced back yard. A pellet grill is on the deck as well for outside cooking

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Top Guest favourite
An aerial view captures a spacious guest house surrounded by manicured lawns and vibrant flowers. Nearby, a vegetable garden is visible alongside other landscaped areas. The green metal roof complements the natural setting, with orchards and trees in the background under a soft sunset glow.
Guesthouse in Beaverton
4.97 out of 5 average rating, 183 reviews

SCHOLLS VALLEY RETREAT

This country 5-acre setting has a 1 BR, 1 Bath 1,664 sq. ft. guest house that is filled with tons of natural light. Views of the Scholls Valley countryside, a gorgeous sky, manicured yards filled with multiple areas of lawns, abundant flowers, shrubs and trees. It is on a private dead-end road. Come to enjoy its peace and tranquility and also close by to multiple Wine tasting venues, the luxury Allison Inn and Spa, ocean beaches, and so much more!

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Top Guest favourite
An inviting entrance showcases a fountain surrounded by lush greenery and stone pathways. The front door, framed by ornate pillars, opens to a well-lit interior. Soft lighting enhances the welcoming atmosphere, with a seasonal wreath adorning the door.
Home in Sherwood
4.96 out of 5 average rating, 160 reviews

Chateau Chardonnay:Tuscan home in NW wine country

Equipped with two HEPA air filtration systems that work continuously to filter and sanitize the air, this home is a clean and safe space to relax and enjoy nature! The house sits on 4 acres in the picturesque Oregon wine country. The back deck looks out over a lush back yard that cascades down to a lazy creek. Gaze out the large kitchen window to the paver patio, vibrant lawn and rimmed with beautiful mature landscaping, koi pond and fountain.

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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, 223 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.

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Top Guest favourite
A charming sign reading 'Willow Creek Cottage' is mounted on a yellow wooden wall. Lush greenery surrounds the entrance, adding a touch of nature to the welcoming facade.
Guesthouse in Wilsonville
4.95 out of 5 average rating, 581 reviews

Willow Creek Cottage

Enjoy country living in our charming and unique 1890s guest house. Situated on 12 acres in horse country. No fee for pets. Great location - 20 minutes to Portland, 25 minutes to Oregon Wine Country, 90 minutes to the coast and five minutes from I-5 and Wilsonville. Bedroom with comfy pillow top queen bed. Breakfast nook with refrigerator, microwave and Keurig coffee maker. Direct TV and WiFi.

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Guest favourite
A bright dining area features a round wooden table surrounded by black chairs. Large windows allow natural light to fill the space, revealing views of the outdoor patio and landscaped yard. A fireplace is positioned against a stone wall, adding a cozy focal point.
Home in Newberg
4.88 out of 5 average rating, 102 reviews

River Wine Farmhouse

Located on the Willamette River on 2 acres just minutes from wine country and fine dining. Two King bedrooms, 2 full baths and loft with murphy bed. Gas fireplace, heated floors, private patio and pool table. No river access on the property, parks with river access in Newberg and Wilsonville. Owner lives in separate home on the property, no closer than other neighbors.

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Popular amenities for Chehalem holiday rentals

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