
Vacation rentals in Chehalem
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Top-rated vacation rentals in Chehalem
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Willamette Valley Wine Country Hub
Located in the heart of the Willamette Valley wine country the 1100 SqFt private unit provides a unique opportunity to experience the north west. We are at the center of a hub with equal access to Hillsboro, Sherwood, Newberg and Beaverton for all of the night life and restaurants while being within a few miles of 100+ wineries. We also offer a wood fired pizza making experience (see below for details). All of this while experiencing rural Oregon. We are on 6 acres with only a few neighbors.

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.

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

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.

Wine country retreat with amazing views
This lovely tree top space is attached to our home and includes separate entry, complete privacy in the unit, has its own upstairs deck, and includes the use of our shared lower deck and hot tub. The kitchen is a "kitchenette" with no stove, but we do provide a single burner hot plate. Come practice "Shin Rin Yoku", the the stress- reducing essence of the forest. Trails, benches and platforms throughout the property provide a place to sit, enjoy the clean air, meditate, or do yoga.

Old Town Retreat - Best place in Old Town Sherwood
At the gateway to wine country, our peaceful Old Town 1916 craftsman home brings historical charm with many amenities right in the heart of Old Town Sherwood. Sleeps 9 with 6 new beds, 2.5 remodeled baths and an open kitchen with gas range, everything you need for a few or many. Owner occupies the basement and rear separated dwelling on property. However, both the basement and rear dwelling are completely locked off and have entirely separate entrances. The best place in town.

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

Cozy Wine Country Suite
A cozy suite with private, separate entrance and garden, located a short walk to Sherwood’s charming downtown. Quick access to coffee shops, restaurants, and a local brewery. Close to many of the valley’s best tasting rooms and vineyards. Relax with a glass of Pinot Noir and watch the sunset on your private deck, or take a short drive to Portland and explore the city. Sherwood is centrally located and the perfect distance for a day trip to the coast or the mountains.

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!

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.

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.

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.
Popular amenities for Chehalem vacation rentals
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Destinations to explore
- Silver Falls State Park
- Moda Center
- Laurelhurst Park
- Oregon Zoo
- Oregon Convention Center
- Providence Park
- The Grotto
- Portland Japanese Garden
- Enchanted Forest
- Beacon Rock State Park
- Airplane Home
- Tom McCall Waterfront Park
- Wonder Ballroom
- Oaks Amusement Park
- Sellwood Riverfront City Park
- Washington Square
- Arlene Schnitzer Concert Hall
- Tryon Creek State Natural Area
- Reed College
- Hoyt Arboretum
- Pittock Mansion
- Powell's City of Books
- Evergreen Aviation & Space Museum
- Wings & Waves Waterpark





