Holiday rentals in Chehalem

Oxberg Lake Retreat, lake & farm view in wine ctry

A storybook oasis with lake/farm views. Enjoy your morning coffee or evening wine while listening to the sheep and chickens. One loft bedroom, one full bath with large living room/kitchen. Hosts live in attached home, but you have full privacy. * 5 min to George Fox University * 2 min to The Allison Inn & Spa * 50+ wineries within 10 min drive *Walk to Farm Craft brews at Wolves and People on Benjamin *Enjoy canoeing, feeding the sheep, or reading a book by the fire pit. roll-away bed available

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.

Our Cottage on Champoeg, St. Paul, Oregon

1 or 2 guests (sorry no children, infants or pets) will enjoy your stay in our charming, comfortable cottage located on our 65 acre farm in the scenic Willamette Valley. Enjoy amazing sunsets from a full size deck overlooking fertile farmland. Fully equipped kitchen with all the necessities for a gourmet meal. There are more than 50+ wineries within 10 miles. In addition, breweries, restaurants and shopping located within 30 minutes. Our Cottage awaits you for a special lodging experience.

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.

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.

Cozy Willamette Valley Cabin With Modern Comforts

A cozy retreat on the brink of Oregon's wine country, walking distance to local restaurants and shops. Enjoy being less than 30 minutes from Portland International Airport and some of the most acclaimed wineries in Oregon's Willamette Valley. This luxurious cabin features a full sized kitchen, washer/dryer, bedroom with queen bed and separate office/dressing room, gas fireplace (out of order), smart TV and second queen pull-out. The full bath features walk-in rain shower and full vanity.

Mama J's

For whatever brings you to Oregon, stay at Mama J’s comfortable, peaceful, safe and convenient spot. Portland is just ten miles away, the closest beaches, Columbia River Gorge and Mt. Hood are all about an hour, and there are numerous hikes from the forest right down the street to Silver Falls and beyond. The neighborhood is peaceful and your private patio is the perfect place for a beverage and some bird and squirrel watching. If it rains, hang out in the gazebo! Hope to host you here!

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.

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.

Charming Winery Getaway ~ Comfy and Cozy

When guests aren’t exploring local wineries or hiking waterfalls, they’re unwinding; lounging at the picnic table, strolling with their pup, or cozying up with a book from our unique library. This bright and stylish tiny space has it all: two comfy beds, a refreshing open-air shower, generous counter space for work or dining, a fully stocked kitchen, a large BBQ, and a pet care kit. Craving downtime in the fresh air? You’ve found the perfect getaway!

Carly's Comfort Inn

Great location for wine country enthusiasts, and so much more. Five minutes to Old Town Sherwood for dining and wine tasting. Nearby wineries include Hawk's View, Blakeslee Vineyard Estate and Alloro Vineyard. Carly's Comfort Inn is the hub for exploring Willamette Valley wineries, the coast, Silver Creek Falls, Columbia Gorge or Mount Hood. A day trip in any direction and a cozy place to return to at the end of the day.

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.