Holiday rentals in Sherwood

Sherwood Inn - in Charming old town Sherwood

LOCATION! We have it!! Charming 4 bed/1.5 bath house in Old Town Sherwood, the Gateway to Oregon's Wine Country and all that the Dundee Hills/and Yamhill Carlton has to offer. Our remodeled house is walking distance to local restaurants, bars, wine bars, bakeries,antiques and a super cute coffee/whiskey house with a fire pit next door. The Library as well as several parks are close by. Plan your vacation or business trip with us in Sherwood and the enjoy what surrounding areas have to offer!

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.

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.

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.

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.

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.

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.

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.

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.