Pet-friendly vacation 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.

Charming home on private street with hot tub

Keep it simple at this conveniently situated retreat, just a 10-minute drive from downtown Portland and moments away from Multnomah Village. Nestled at the end of a private street in a desirable neighborhood, this charming home offers a spacious interior (with recently added centralized A/C) and inviting shared outdoor spaces. Relax and unwind in the hot tub, gather around the barbecue, or enjoy the patio and fireplace. Remote worker? Come be productive in our sitting/standing desk station.

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.

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.

Wine country retreat with amazing views

This lovely tree top space is attached to our home and includes separate entry, complete privacy in the unit, has its own upstairs deck, and includes the use of our shared lower deck and hot tub. The kitchen is a "kitchenette" with no stove, but we do provide a single burner hot plate. Come practice "Shin Rin Yoku", the the stress- reducing essence of the forest. Trails, benches and platforms throughout the property provide a place to sit, enjoy the clean air, meditate, or do yoga.

A Cute, Clean, & Comfy SW Portland Guest Apartment

Jasper House is a very clean, pet friendly one bedroom "in-law" apartment in Garden Home. Located on a quiet Culdesaq. Easy access to 217 and I-5. The perfect West side location, close to everything. Great for business and pleasure travelers a like! No additional pet fees for up to 3 pets! This 450 sq ft apartment has a private deck, cozy sitting room w/double futon, 40" TV w/Roku, dining table & kitchenette. The bedroom has a comfy King bed & vanity/desk. We have A/C as well!

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.

Spectacular Valley View in Wine Country

Relax and enjoy the best of what Oregon Wine country has to offer in our newly renovated country home. With a stunning view overlooking the Willamette Valley, you are close to over 300 wineries and tasting rooms, local craft beer, and a great social atmosphere in our small town. Enjoy soaking in the hot tub or having dinner outside under the gazebo. Have your pets outside, worry free with a large fenced back yard. A pellet grill is on the deck as well for outside cooking.

Multnomah Village Hideout

Explore our new, artist-built bungalow in Multnomah Village, Portland. This cozy space sleeps four with a queen bed upstairs and a pullout couch downstairs. Steps away are charming cafes, shops, and a park with hiking trails and dog parks. Enjoy local activities like bingo and dining on pet-friendly patios. Complete with essentials including laundry and a breakfast nook, this bungalow is perfect for both short and extended stays, offering a unique Portland experience.

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 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!

Willow Creek Cottage

Enjoy country living in our charming and unique 1890s guest house. Situated on 12 acres in horse country. No fee for pets. 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.