Vacation rentals with outdoor seating near Old Mill District

Sunny Bend Stadium House Getaway! Sweet Deck!

Adventure-ready, with everything you’ll need to enjoy Bend, this family-friendly cottage in SE is close to great dining, shopping, and trails. Visit delightful brunch spots or cook up a stack of waffles in the fully stocked kitchen. Enjoy the fire pit, sunny deck, and fenced yard. Check out nearby breweries, stroll along the Deschutes River, explore biking & hiking trails, mountain biking, or a Bend Elks baseball game! Book this bungalow as your perfect basecamp for exploring Bend year-round!

Location! Bungalow River & Beach Access

Welcome to our Century-Old Craftsman Bungalow on Riverfront Street. This one bedroom, one bath sleeps two to three. Enjoy a fully equipped kitchen, floor to ceiling river rock gas fireplace, inviting front porch, back deck with propane BBQ, table/ chairs. The Bungalow has a peek of the river, as it is considered the "guest house" to the larger "main house" it shares the lot with. Enjoy low bank river access to launch your kayak. Park the car and experience the best Bend has to offer.

Downtown Craftsman with King Bed and Private Yard

Stay at a rare home in the core of downtown. A beautifully restored 1922 craftsman with plants and warm wood throughout including natural light from vaulted ceilings, charming architecture and paintings by local artist Sheila Dunn. Walk to dozens of restaurants, breweries, coffee and shops. Cross the alley to food trucks and frequent live music or relax in your private walled courtyard. No parties or pets please. Trip insurance recommended if illness, weather or smoke may be an issue.

Curated Comfort | Quiet, Clean, Beautiful Design

Enjoy modern style and convenience in this recently built guest home. Flooded with natural light, this spacious retreat is in a welcoming neighborhood - the perfect place to relax. Enjoy morning coffee on the sunny porch or walk to Larkspur Trail and Pilot Butte State Park. Explore Mt. Bachelor, the Deschutes River, and Smith Rock, all close by. Downtown is just a quick 5-minute drive. Everything you need is nearby, whether it's fine dining, outdoor adventures, or local shopping.

Old Mill Studio - walk to concerts, river, dining

Your own private studio behind our home is in the quiet, quaint neighborhood on the bluff above the Old Mill District and Deschutes River. Short walk to restaurants, coffee, breweries and concerts. Close to the river for floating, SUP, River Trail. Easy access to Mt Bachelor, Cascade Lakes, and mountain fun. Private entrance and sliding doors out to a private patio for your morning coffee or end-of-day beverage. A fire pit is available to top off a cozy evening (see notes.)

Airy Bend Oasis - Two Ensuites

Cheers to your stay at Bent Pine Oasis, located in the picturesque west side of Bend! This home provides the ideal location for any outdoor enthusiast: Mt Bachelor's slopes are just a 20 minute drive & the Deschutes River Trail is mere steps from the front door- your avenue to biking, running and exploring Bend. Looking for a more relaxing day? You can make the 5 minute drive into the Old Mill District to enjoy food trucks, a river float, or fresh hops at a local brewery.

Modern Apartment Perfect For Couples (Dogs Too!)

Adorable and modern apartment bungalow on the east side of Bend with a little private yard, deck, kitchenette, and dedicated workspace. Equipped with everything adults, and pets need to relax, work and explore the beauty and adventure of Central Oregon. The location is ideal with quick access to everything in Bend. Downtown is a 10 min drive, and Mount Bachelor is 30. This 300-square-foot apartment is the perfect home base to explore Bend!

Old Mill ~ Deschutes River

Desert Sun is the perfect place to enjoy all that Bend has to offer. You'll have the Deschutes River right around the corner where you can access floating, fishing, kayaking, SUP or walk/running the 3.5 mile River Trail Loop. The Old Mill District and Les Schwab Amphitheater are a short walk along the river. This home's location makes for a perfect retreat with convenience of being close to Downtown, Mt Bachelor and Cascade Lakes.

Best for Old Mill:River Trail, Views & Town

Awesome location! Fast internet, Wi-Fi. Clean and close to everything that is great in Bend - the river, Mt. Bachelor, restaurants, nightlife, cycling, kayaking, paddle boarding, hiking, breweries, concerts and so much more. You’ll love the location, ambiance, the outdoor space, and the comfy bed. Walk along the river trail to experience what everyone loves about Bend. Easy drive to Mt. Bachelor, approximately 25 minutes.