Pet-friendly holiday rentals in Sherwood

Recreational Family Fun & Adventures Await

Entertain outdoors in a covered lit patio with grill and cooler. Stay warm with 2 propane firepits or by the campfire pit. Fenced in yard is pet friendly. Nearby Rec Center offers a Gym, Splash Pad, and Indoor Pool with Water Slide ($7 Day Pass). Enjoy basketball, baseball, soccer, and tennis all walking distance with our sports equipment. Explore many nearby parks with playgrounds and trails with our bicycles. Short drive to Washington Square Mall, restaurants, grocery stores, and more!

Peaceful Garden House in SW Portland

This darling 1940's home sits on 1/4 acre and is nestled in a peaceful neighborhood in Southwest Portland. It gets tons of natural light, has greenery from every window, is super private and full of vintage charm and character. The home has served as a source of inspiration for the artists, writers and herbalists who’ve lived here throughout the years and now you can experience it for yourself! If you’re looking for an oasis of calm just outside of Portland, you've found the perfect spot.

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.

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 treats 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.

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!

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.

College Street House

Make yourself comfortable in this charmingly updated home in the heart of wine country. This house has everything you need to rest, relax, and enjoy your stay in Newberg. Just 1/2 block from the bustling downtown area with its many restaurants, coffee shops, bakeries and wine tasting, you will also be centrally located to George Fox University and minutes away from hundreds of beautiful wineries.

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.