Pet-friendly holiday rentals in Sherwood

Willow Creek Cottage

Enjoy country living in our charming and unique 1890s guest house. Situated on 12 acres in horse country. Great location - 20 minutes to Portland, 25 minutes to Oregon Wine Country, 90 minutes to the coast and five minutes from I-5 and Wilsonville. Bedroom with comfy pillow top queen bed. Breakfast nook with refrigerator, microwave and Keurig coffee maker. Direct TV and WiFi. **Please be assured that we continue to take all steps necessary to sanitize and air the cottage before your visit.

Private beach and swimming hole nestled in trees

The River Cottage has a treehouse vibe, nestled into the privacy and serenity of the trees! Fishing, kayaking, swimming or relaxing in your private hot tub, right on the Lewis River. This is the place to make memories and enjoy time with family and friends. Swim from your private beach, roast marshmallows, vist nearby falls, enjoy a bottle of wine and relax with the comforts of home! Can't book now? Wishlist us for later! See also our listing for River Haven! Winery tours also available!

Beautiful Dog Friendly Cottage on a 10 Acre Estate

A little slice of heaven. Stay near the heart of wine country on a 20 acre estate and Hazelnut Orchard. Enjoy a complimentary bottle of Oregon wine and light bfast items & snacks upon arrival. Settle in and sit on your personal porch surrounded by Hazelnuts and Dahlias. Or take a dip in the hot tub by the garden and play a little basket ball on the sports court. Close to numerous wineries, breweries, equestrian centers, just 20 miles south of Portland and 60 minutes from the beautiful coast.

Cooper Mountain Tiny Cabin

My Tiny Cabin is located on 2.3 forested acres in a rural setting close to Portland and wine country. My home is located on the same property but trees and space between the two provide privacy. A ladder leads you to the upstairs loft with a queen bed and a skylight for a view of the treetops. A futon that folds into a comfortable full sized bed is located downstairs. The kitchenette provides a microwave, small refrigerator and coffee. Step out to the deck to cook on the propane grill.

Cozy 2 bed, 1 bath, private backyard in Sherwood

Whether you are visiting family, on a getaway, going wine tasting, or want to be close to Portland but not in it....you will feel right at home staying in our 2 bedroom, 1 bath duplex! (This is half of the duplex- all one level- LEFT SIDE). You can 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.

Spectacular Choice: Sleeps 6, Your Dog Welcome Too

This bright, clean and stylish home has everything you need to make your visit comfortable and welcoming. Relax in the living room after your travels with Firestick/Roku TV. Prepare meals and mix cocktails in the well-equipped, functional kitchen. Enjoy the pristine bathroom with tub/shower and elegant marble vanity. Two bedrooms and a living room sofa bed will sleep up to 6 guests. Washer/dryer. Large deck with patio and BBQ. Dog friendly backyard. Parking for up to four cars.

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.

Cozy Country Bungalow

*Cozy studio apartment on ten-acre farm. *One queen-size bed *Complete kitchen w/ range, dishwasher, microwave, refrigerator, toaster, and coffeemaker. *Large bathroom, sleeping area with queen bed, living/dining area, and washer and dryer access. *Wireless internet and wall-mounted 40" Smart TV with Netflix. *Relax on your private veranda, or go for a stroll on our 10 acre property. *Enjoy a picnic in the woods. Creek, pond, bridge, & view to enjoy.

Sip & Stay - Charming Tiny House Near Wineries

🍷 When our fun-loving guests aren’t exploring local wineries or 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, stylish retreat has it all: two comfy beds 🛏️, a fresh-air shower 🚿, ample 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 it!