Vacation Rentals

Welcome to Crestline View! This airy and spacious home has amazing views of the Deschutes River year round. You will enjoy mountain views as well as lots of local wildlife. Summer brings out the river floaters of all shapes and styles. Doggies frolic and swim year round in the dog park on the other side of the river. And resident osprey patrol the river while local and migrating water fowl…...

Welcome to The Federal House! This classic Westside Bend home is fully furnished for your Bend getaway for summer or winter activities! Located between downtown and the very popular Galveston and Newport Avenues. This is one of the best locations in Bend and a prime location to explore all Bend has to offer! DOWNTOWN LOCATION Just two blocks from 10 Barrel Brewing and Sunriver Brewing, and only a 15-minute stroll…...

Here is your chance to experience an amazing straw bale home in one of Bend's best locations! This eco friendly, lofted home is the perfect perch for either work or play in Bend. Located on a quiet street just a block from Drake Park you can walk to coffee every morning, walk to your river float every afternoon and truly experience the relaxing routine of downtown Bend living. On the…...

Welcome to the Basalt Bungalow! The Basalt Bungalow is a fully furnished two bedroom, three bed (1 king, 1 queen, 1 queen sleeper sofa), one bath home located in the ever popular Westside Newport Avenue Neighborhood in Bend! The Bungalow welcomes you with a large covered porch and private fenced yard with a large hot tub to soak in anytime of the year! Perch with a good book in the…...

This sweet cottage is a completely refreshed 1910, craftsman bungalow. Welcome to the Sugar Plum Cottage. This fully furnished home has been head to toe remodeled in 2023 and has 1 bedroom (Queen), 1 bathroom and a Queen pull out sleeper sofa. Snuggle in and enjoy the very best Bend has to offer. Just 1 block from the delicious food cart lot and all of the cafes, restaurants and breweries…...

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…...

Welcome to the westside 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…...

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…...

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…...

Ready just in time for summer! Welcome to your downtown Bend retreat. Sunshine Daydream is IN Downtown Bend. This sweet and completely redone 1941 cottage is fully furnished with 1 queen 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.…...

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…...

Enjoy playing around Bend (hiking, Ale Trail, SUPs, mountain biking, skiing, shopping, l) and retreat back to Bend's premier River West neighborhood for a peaceful night sleep. Heart of Bend is kid & pet friendly. Fully stocked kitchen. Modern feel. And a fenced in private patio for relaxing. Heart of Bend is a charming 3 bed, 1 bath home located on Bend’s popular West Side right in the heart of…...

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…...

The Bella Bird Bungalow is a completely renewed 1910 solar, craftsman cottage. This solar powered, fully furnished home has 3 bedrooms (1 King, 1 Queen, 2 Twins) and 2 bathrooms. Snuggle into your private, sweet bird nest and enjoy the very best Bend has to offer. Delightful details will surprise and charm you in this very sweet westside home. Just 1 block from the delicious food cart lot and all…...

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…...

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…...

Welcome to your cozy and classic cottage for your downtown Bend adventures! You'll love this delightful space! Plenty of space for relaxing and dining for 6 adults... if you can share the 1 bathroom! This bungalow home is comfortable and open, perfect for catching up with friends and family inside and out. The back patios are open and a BBQ is waiting for you too! Grab a book, a friend…...

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. DOWNTOWN LOCATION You are a mere 2 blocks from everything downtown...some of Bend's finest restaurants, breweries and entertainment. Grab a bike and roll (remember…4 cruiser bikes provided!) or just stroll into the very heart of Bend. Feel like exploring…...

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…...

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…...

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.…...