Family-friendly vacation rentals in Sherwood

Suite in Hilltop Home in the woods w/King Bed

Enjoy a peaceful retreat in a comfortable and inviting suite in our mountaintop home in wine country. The basement suite is attached to our garage that you walk through to access. It's an open studio and has a relaxed feel with super soft bedding on a king sized memory foam mattress. The suite is surrounded by trees and has large windows to provide a woodsy feel near the city. Nike and Intel are close by and Cooper Mountain Vineyards is also 2 miles away. 30-40min drive to downtown Portland.

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.

Lovely place in Sherwood!

You will be close to everything when you stay at this centrally-located place! No matter the reason you are in town, you will feel right at home staying in our 2 bedroom, 1 bath duplex! (This is half of the duplex- all one level- RIGHT SIDE). You get to enjoy the private fenced back yard, fenced front yard, and 1 car garage. It is located close to wine country, lots of parks (including dog parks), VERY close to local restaurants, shopping, family game center (Langers), and highway 99W.

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.

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 Fall 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!

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.

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.

Beaverton Vintage Tiny Home

Have you ever wondered what it's like to stay in a Tiny Home? Our Tiny Home away from Home has everything you need to relax, live a little and have fun. Our location is in the burbs just 15 minutes west of downtown Portland and minutes to Nike World Headquarters. The Tiny Home has a kitchenette, full bath, w/d, living area, queen bed loft, and personality galore!