Historic Downtown Bend

Coming soon on Nov 8th! We are so excited to host you in this beloved downtown tiny home. Little Lava is switching management on November 8th and we can't wait to host you! Welcome to Little Lava in Downtown Bend! Here it is! A tiny home that is smack dab in the heart of downtown Bend. Just around the corner from McMenamins and everything downtown. This charming home will be the perfect…

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.…

Welcome to Middle Sister Bungalow! The Middle Sister Bungalow is the middle unit of three attached but completely independent homes in this renovated, 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…

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 Fir Millhouse! This lovely home is 1 of 2 beautifully restored homes located in the Jefferson Millhouse. This historic bungalow duplex is located just blocks to the river, downtown AND the Old Mill district. You'll love parking your car and walking all over some of the best spots in Bend. This house was upgraded down to the studs with fastidious attention to historic details in 2014. This millhouse was…

Welcome to the Oak Millhouse! This lovely home is 1 of 2 beautifully restored homes located in the Jefferson Millhouse. This historic bungalow duplex is located just blocks to the river, downtown AND the Old Mill district. You'll love parking your car and walking all over some of the best spots in Bend. This house was upgraded down to the studs with fastidious attention to historic details in 2014. This millhouse was…

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…

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…

Coming soon on Nov 8th! We are so excited to host you in this beloved downtown home. Big Lava is switching management on November 8th and we can't wait to host you! Welcome to your Downtown Oasis! Big Lava is home IN Downtown Bend! Fully Furnished with 3 king beds, this sparkling home built in 2018 soars overhead with vaulted ceilings with windows that bring the outside in. Smack dab in the…

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.…

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…

The Bernhard-Justice Bungalow is a classic 2-bed, 2-bath 1926 home with lower level family room and additional den/sleeping area. This home features a large yard, hot tub and is centrally located in the heart of the Bend Old Town Historic District. Listed in the Bend Register of Historic Homes and named after the original families who owned the home. This vintage bungalow maintains its historic charm with all of the modern comforts…

DOWNTOWN LOCATION This is where all the best neighborhoods meet...downtown, Old Mill, Westside...this is the location you are looking for in Bend. So walkable, you will likely park your car and walk to your concert at the Hayden Homes Amphitheater, walk to your dinner in downtown Bend, walk to the surf wave and river float, walk to shopping in the Old Mill. Historic District in Bend! Coffee is half a block away…

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 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…