Pet-friendly holiday rentals in Sherwood

Luxury Wine Country Estate

Welcome to Luxury Wine Country Estate, an oasis where luxurious refinement meets the epitome of wine country indulgence. Revel in unmatched hositality, thoughtfully designed to include Tempur-Pedic suites, therapeutic hot tub, rejuvenating sauna, invigorating cold plunge, and the most stunning valley and vineyard views. Every touch is meticulously crafted, from heated stone floors and Dyson innovations to dual gourmet kitchens, Yeti picnic essentials, EV charging capabilities, and so much more.

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.

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.

Serene Forest Studio - Walk to Multnomah Village

Nestled in Portland's captivating woodland, this freshly renovated studio offers the perfect escape. Just a mile from Multnomah Village, steps from Alice Trail, and a few blocks from I-5, our retreat combines seclusion with convenience. Enjoy the tranquility while being a mere 10-minute drive from downtown. With thoughtful furnishings for comfort and ample privacy, it's an ideal spot to unwind after exploring Portland's vibrant attractions. Experience the unique charm of our city with ease!

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.

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!

Outdoor Fireplace & Pup Friendly

Centrally located between Portland & Newberg Wine Country, our quaint 1949 home is walking distance to shopping, stores & food. The neighborhood is clean, friendly and safe. Public transit is close by. It is an old home but newly restored. Easy freeway access. Enjoy a glass of wine on the covered patio with a crackling fire in the outdoor fireplace. Backyard is fully fenced for pet and child safety.