Vacation Rentals

Welcome to your downtown historic retreat. Cecil Sly is IN Downtown Bend. Fully Furnished with 1 king bed and modern amenities, this historic home is registered with the National Register of Historic Places. Warm, inviting and centrally located, this classic and walkable home is just a few steps to Downtown Bend. Perfect for your next Bend stay. DOWNTOWN LOCATION Downtown Bend is your front yard from this historic perch. Walk anywhere downtown…

Welcome to South Sister Bungalow! The South Sister Bungalow is one of three attached but completely independent homes in this unique and historic triplex. A classic example of early 1900's living, you'll love having Bend at your front door. The grassy back lawn and dining area are perfect for summer picnics. Enjoy a dedicated parking space and a very charming bungalow home. Perch on your front stoop and watch Bend walk and…

Welcome to the Riverside Condo! Cozy, top floor 2-bed, 2-bath condo in a riverside complex just 2-3 blocks from Downtown Bend! Saunter to the river, play in the park, or cruise to downtown Bend. You'll love having a fully furnished kitchen for cooking, gas fireplace, A/C, and 2 balconies overlooking the common courtyard! DOWNTOWN LOCATION The River Retreat Condo is only a skip to downtown Bend! With the Deschutes River, Bend River…

Welcome to Green Gables Estate, a spacious, warm, and vintage-but-modern home featuring 3 bedrooms (king, queen, queen), den/media room with queen Lazy Boy sofa with inflatable mattress, and 3 full bathrooms. PLEASE NOTE: As of July 15, 2026, there is an active construction project taking place approximately two houses down from the property. Guests may occasionally hear construction noise and see heavy equipment during normal daytime working hours. We aren’t able to…

Welcome to the Basalt Bungalow! This fully furnished two-bedroom, three-bed (1 king, 1 queen, 1 sleeper sofa), one-bath home is in popular Westside Newport Avenue Neighborhood, Bend! Enjoy the large covered porch, private fenced yard, and hot tub year-round! Relax in the bay window in the living room or find a cozy nook outside. You'll love this westside getaway! DOWNTOWN LOCATION Steps from local favorites! Get treats at Nancy P's and fresh…

Welcome to North Sister Bungalow! The North Sister Bungalow is the largest of the three attached but completely independent homes in this unique and historic triplex. A classic example of early 1900's living, you'll love having Bend at your front door. The grassy back lawn and outdoor dining area are perfect for summer picnics. Enjoy a dedicated parking space and a very charming bungalow home. Perch on your front stoop and watch…

This lovely home is ready just in time for Memorial Day! Welcome to St Helens Cottage, a sweet, warm and inviting vintage-but-modern home featuring 2 bedrooms (king, queen) and 1 bathroom. DOWNTOWN LOCATION You are a mere 2 blocks from everything downtown...some of Bend's finest restaurants, breweries and entertainment. Take an easy stroll into the very heart of downtown Bend, the Old Mill or the Deschutes River. The best of the westside…

Welcome to your downtown Bend retreat. Sunshine Daydream is IN Downtown Bend. This sweet and completely redone 1941 cottage is fully furnished with 1 king bed, 1 sleeper sofa and modern amenities. This home is perfect exploring all of downtown Bend! DOWNTOWN LOCATION Sunshine Daydream is right on the edge of bustling downtown Bend. You can walk anywhere downtown in just a few minutes. This is a small pocket neighborhood full of…

This spacious and Old Mill home is fully furnished for your Bend getaway! Vintage and modern all at the same time...You will love this completely updated kitchen and the cool, mid century furnishings. This charming vintage-modern home is adorable inside and out. A classic wood burning fireplace will warm and welcome you home on cool nights. This home has central heat too! Original hardwood and modern cork floors rest underfoot. Graceful archways…

Welcome to the west side of Bend and the Cinder Cone Cottage. You want the best location in Bend for your getaway, and you'll find it here. This newly renovated cottage is in one of the best neighborhoods in Bend! Walk 1 block to shops and restaurants on Galveston (10 Barrel, The Victorian Cafe, Ida's Cupcakes, the Food Cart Pod, and much more). So convenient to the very popular west side Galveston…

Welcome to Mill Modern. Completely rebuilt in 2023, this completely refreshed, historic, bungalow is located in Bend’s best historic neighborhood. This two-bedroom (queen, queen), two-bathroom bungalow is a great option for modern, design-conscious downtown lodging. Enjoy a piece of history in this peaceful, centrally located retreat. Two blocks from Downtown, two blocks from Box Factory and Old Mill, and just an 8-minute walk to the Deschutes River and the famous river wave.…

Welcome to Cascade Cottage! Modern and charming, this sweet Old Mill era home is fully furnished for your Bend adventure. Modern furnishings, updated kitchen, easy dining for 6 inside or outside. You will love the simple clean lines of this updated home! Perfect for lounging, inside and out. Out front, you'll find a sweet porch overlooking the street. Just off of Portland Ave, you'll see lots of neighbors coming and going from…

The Aspen House cozy home is a great place to relax and enjoy all that Bend has to offer. A classic Bend millworker’s house at its roots, it's been modernizing while keeping the Old Bend feel. Look for creative reuse and recycled materials and enjoy energy efficient systems to keep you just the perfect temperature. This cozy home is a great place to relax and enjoy all that Bend has to offer.…

The RiverBend Bungalow is a sweet riverfront hide-away on the super popular westside of Bend. Enjoy your riverfront perch from the outdoor deck, hot tub or from the living room where you can watch the stand up paddle boarders and floaters drift by OR join them! Choose the RiverBend Bungalow for your next Bend getaway. Experience all that Bend and Central Oregon have to offer and enjoy this quality crafted vacation home…