Pet-friendly holiday rentals in Bend

<SALE> River Canyon Retreat | Dogs | Old Mill |

Welcome to the River Canyon Retreat! A peaceful, pet friendly, single level home filled with fun and hip upscale décor. Enjoy hiking the Deschutes River Trail and walking or biking to the shops and breweries in the Old Mill District. Miles of Mountain bike trails and the road to Mt. Bachelor and Cascade Lakes are close by. Cozy up to the wood burning stove with a good book or enjoy the forested hillside full of birds, deer and all sorts of nature on the back porch. Welcome to your Retreat!

House on the Hill in Bends River West Sleeps 8!

Private Westside Location! Dog friendly! Bends Best location! Available for monthly and long-term stays, just ask! Gorgeous private four bedrooms, three full baths!Private Hot Tub. Luxury open floor plan and deck. A minute to Newport Market and restaurants. A spacious gourmet open kitchen, a wrap-around bar that opens to the living room, fireplace, and dining room, perfect for entertaining your guests. Extra family room with ping pong table. Comfy beds and pillows! Close Mt.Bachelor Ski Resort.

Romantic Farmhouse near Mt. Bachelor

Relax at a peaceful farmhouse for a romantic weekend, or take your time exploring Bend with friends. Baltzor Farm and Guesthouse is fewer than 2 miles from some of Bend's amazing breweries and restaurants. Smith Rock and Mt. Bachelor are both within 30 minutes of the guesthouse. Catch a concert, float the Deschutes, or go on a bike ride. Our relaxing farmhouse has rustic, old-world charm with all of the modern amenities, including a soaking tub, waterfall showerhead, soft linens, and Starlink.

Quiet Modern Home | Dog Friendly | 8 Min to Town

This modern home is the perfect place to relax after a long day of enjoying Bend’s endless outdoor activities. A peaceful retreat, complete with upscale furnishings, tons of natural light, and a fenced backyard with a charming garden and fire pit to enjoy the Bend outdoors. Plenty of storage for your mountain bikes and ski equipment in the garage! Fully stocked kitchen. Super Fast Wifi for Remote work! 4 Min Drive Lone Pine Coffee and 10 Barrel 10 Min Drive to Downtown Live like a local!

The Blackberry Cottage

This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.

River Run Bend Bungalow & Romantic Spa Grotto

**NEWLY INSTALLED! ** Spa & sauna grotto is all ready for your romantic Bend getaway! This quiet, wooded, centrally located, standalone bungalow is steps from the Deschutes River trail, easy walking distance to Mill Dist. and Hayden Amphitheater. It boasts a comfy king bed w/premium down bedding & pillows, dedicated free parking (+ extra cars or small RVs), outdoor dining and patio area, washer/dryer, and a kitchen fully stocked with everything you need for fun and relaxation for all seasons!

West Side Bungalow, Hot Tub, One Block to River

The Drake West Bungalow is an adorable one bedroom, one bathroom home in the River West Neighborhood near the Galveston Avenue District. It is located just one block back from iconic Drake Park along the Deschutes River, and one block from popular Galveston Avenue with its eclectic shops and restaurants. Just a half block away is The Lot food truck court with amazing outdoor seating open year round and local beer on tap. It is a quintessential historic Bend cottage with unbelievable charm.

Dog-friendly | Hot tub | Close to everything

Looking for relaxation in a peaceful setting that's still close to everything? You've come to the right place! Situated on a quiet cul-de-sac, Cozy Canterbury is surrounded by natural beauty making it the perfect getaway from the daily grind. Featuring hardwood floors, thoughtfully furnished rooms, a large deck with gas grill, hot tub and fire table, our home feels like a remote getaway while still being close to all that Bend offers! All that and dog-friendly, too! (2 dogs max allowed)

The Big Tiny

Reset and rejuvenate at the Big Tiny. Our thoughtfully designed, unique tiny house is fully equipped for your comfort and is surrounded with gorgeous desert views, and is also pet friendly. Conveniently located just 15 mins from downtown Bend. Enjoy all that Central Oregon has to offer. Start your days sipping coffee in the front yard while drinking in the fresh air. Relax after a day of adventure under the starry sky with a local beer or glass of wine next to the propane fire pit.

Have a Patio Barbecue at a Pet-Friendly House in Midtown

Stoke the wood stove with another log and stay warm and cozy in a colorful plant-filled living room with stylish mid-century modern furniture. When the weather's nice, go outside to play croquet or corn toss and roast mores around the fire pit under the stars. Each bedroom has cable TV....large fully fenced in yard . Dogs are welcome. Limit of 3 with a $35.00 Pet fee. No cats allowed. Wood provided. There is a smart lock on the front door, you will be given the code before arrival.

Westside "Bud-And- Breakfast"

The first and only "Bud-And-Breakfast" in Bend, Or, located in the heart of Bend's Westside. Situated above Tokyo Starfish, the unparalleled cannabis dispensary in Central Oregon, this fantastic 2-bedroom apartment isn't just in a great location, but is also cannabis friendly. Just head downstairs to Tokyo Starfish with your complimentary gift card and experience the freshest selection of flower, edibles, drinks and other top cannabis products the dispensary has on hand.

Walk to Amphitheater, 1BD studio w/ view, Old Mill

This attached one bedroom unit has everything you need for your visit to Bend. Mountain views, cozy fireplace, sitting area on private deck, and spacious kitchen are all within walking distance to the Old Mill/Hayden Homes amphitheater. It’s only a few minute drive to downtown and skiing at Mt. Bachelor is 25 minutes from your door. Walk to amphitheater in 15 minutes. Cable, wifi, washer/dryer & ample gear storage. You will feel like this is your home away from home!