Vacation rentals in Sherwood

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.

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.

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.

Jason & Susie's private guest suite w/ kitchenette

Located in NW Portland, our space is in a quiet neighborhood, next to a park and tennis courts. We are 7 minutes from the Nike Headquarters, 2 minutes from Columbia Sportswear Headquarters, and 15 minutes from Intel, making it a perfect stay for your business needs. We are within walking distance to a grocery store, pubs, small restaurants, and the Saturday Cedar Mill Farmers Market. Close by is the entrance to Forest Park, one of the largest urban parks, with 80 miles of trails.

A sunny separate studio w/skylights

Your own modern large studio on 2nd floor with separate entrance, full kitchen, sunroom, skylights, 14-foot ceiling, balcony, desk, full bathroom, washer/dryer, dishwasher, gas stove, lots of windows. All this in a vibrant neighborhood, short walking distance to multiple coffee shops, restaurants, a single-screen movie theater, the light rail station, an open-late grocery store, a small park with a salmon run. One mile to Reed College, where Steve Jobs took a calligraphy class.

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.

Private Apartment at the Farmhouse

Beautiful, private, recently updated upstairs garage (detached) apartment at the farmhouse. One bedroom (with a brand new queen bed!), one bath (shower only), with a spacious living room (hide-a-bed in couch) and full kitchen. A great home away from home. We've even got a desk ready to become your mobile office! A coffee maker and fresh coffee is available for you. Free Wi-fi during your stay. This is a great location in the heart of Tigard/Beaverton.

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.