Holiday rentals with outdoor seating near Old Mill District

Modern retreat in central Bend

Enjoy our new custom-built ADU located a block away from the Deschutes River in a quiet residential neighborhood, just a 10-minute walk from downtown along the River Trail. In this modern, bright, and private space, you'll enjoy the luxuries of hardwood floors, waterfall countertops, a built-in workspace, heated tile bathroom floors, a 55" Smart TV, BBQ and fire pit, and endless hot water—plus off-street parking and EV charger. One king bed, one daybed with a trundle, and one queen sleeper sofa.

River Run Bend Bungalow & Romantic Spa Grotto

Relaxing, private spa & sauna grotto is ready for your romantic Bend getaway! This quiet, wooded, centrally located standalone bungalow is steps from the Deschutes River trail and within easy walking distance of 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!

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.

Location! Bungalow River & Beach Access

Welcome to our 1918 Bungalow on Riverfront Street. This simple, no frills 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.

Nordic Sauna - Near Old Mill - No Pets - Top 5%!

Relax in a beautifully remodeled 1930s mill house featuring a full kitchen, fireplace, landscaped yard, and a genuine Finnish-style sauna. Located just 3 minutes from the Old Mill District with easy Hwy 97 access, yet tucked into a quiet neighborhood. Enjoy a peaceful yard with native plants and a fire table for Central Oregon evenings. A small private backyard is perfect for cooling off after the sauna. Pet-free and cleaned with unscented products for a fresh, allergen-free stay.

Downtown with hot tub and fenced-in yard

Light and bright downtown Bend vacation cottage with a landscaped, fenced yard and HOT TUB. Walk to breweries, restaurants, coffee shops , art galleries and the Deschutes river and river trail. One-bedroom, one-bath unit features a separate memory foam queen hide-a-bed in the living room. Private laundry room. Private parking spaces in back. Open floor plan with vaulted ceilings and automated skylight shades. Complete remodel. Pet-friendly (must add pet to the reservation).

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.

Aspen @ The DUPE - blocks from Old Mill District -

Aspen: Located blocks from the Old Mill District, this beautifully updated 2-bed, 2-bath townhouse blends privacy with an unbeatable location. Walk or bike to the Old Mill, Deschutes River, dining, and the Hayden Homes Amphitheater. Tucked in a serene, tree-lined setting, the private home features a bright kitchen with updated appliances, a primary suite with a walk-in tile shower, and a separate porch with a BBQ grill. The perfect mix of modern comfort and convenience.

Charming Millhouse w/ hot tub close to everything

Unveil Bend's charm at our centrally located 1945 mill cottage – the adventure nexus! Walk to top restaurants, a grocery store, and embrace the Old Mill District, or catch a Bend Elks game. Deschutes River, and Hayden Homes Amphitheater just a short bike ride or walk away. Conquer Mt. Bachelor in a scenic 30-min drive. Your ultimate Bend basecamp beckons! No pet fee!! No chore list at checkout!! Ski, golf, hike, climb, shop, dine, float .... It's all here

Old Mill Charm

Great Location in Old Mill District – Walk to Summer Concerts! ♥ Fenced Backyard ♥ Pet Friendly Nestled in the heart of Bend, Old Mill Charm offers the perfect blend of comfort and convenience. Thoughtfully designed with many amenities to ensure a seamless stay, this charming rental is ideal for relaxing or exploring all that Bend has to offer. There is a tenant in the apartment above the detached garage who does not use the driveway ensuring your privacy.

Adventure Awaits! Walk to downtown and river!

A perfect home base for all your adventures in Bend! Just a 10 minute walk from downtown. Walk or bike to the best restaurants and breweries in Bend. Swimming, hiking, and fishing in the Deschutes river steps from your doorway. King Bed~ Gas fireplace ~ Reading nook ~ Comfy queen sleeper sofa ~ Air Conditioning ~ Games ~ 2 TVs ~ Full kitchen ~ 2 balconies ~ Keyless Entry ~ Shared laundry room ~ 2 Bathrooms ~ K Cup coffee bar ~ Private WiFi ~ Roku TVs

Central Modern Guesthouse with EV Charger

We built this home out of a passion for creating welcoming spaces. Years ago, we renovated a motel on the coast - an experience that sparked our love of hospitality and shapes how we host today. We live around the corner with our kids, a golden retriever, and a few cats. Mike’s a local realtor, and Betsy manages business ops for the local fire department. We love books, music, and helping you discover the best of Bend - trails, eats, and community.