Vacation Rentals

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 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.…

You've been looking for a quiet space with great light for your month (or more) in Bend. You'll find it here! Constructed in 2025, this brand new loft is elevated in all senses. Set high above the street, large windows allow natural light in from all sides. The circular floor plan makes so much sense and allows light and air to pass throughout the entire home. A sweet balcony for a bit…

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…

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…

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…

Welcome to this lovely home in the heart of the Old Mill of Bend! Almost riverfront, this beautiful home is 1 row back from the river. This light bright and lofty home features huge living room windows to bring the outside in. Big sky and horizon views and Deschutes river peeks too. You'll love being so close to the summer river action. Just walk out the front door and cross the street…

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 on Galveston.…

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 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…

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 of the…

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…

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 main floor,…

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 to downtown…

Welcome to Khaya, a LEED certified, solar powered home that is as serious about its carbon footprint as it is about the comforts of home! Khaya will spoil you with its luxurious touches. Your toes will love the heated floors and your senses will delight in the soaring ceilings and plentiful natural light. So spacious, modern and comfortable! DOWNTOWN LOCATION This amazing location on Newport Avenue is within a one-minute walk of…

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 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…

This light, bright, cheerful and modern studio just a couple blocks above all the great shops on Newport Ave. Walk to Newport Market, Backporch Coffee, Spork and more in under 10 minutes. 10 Barrel, The Lot & Sun River Brewing are just a few minutes walk further. Enjoy your very own quiet balcony and tree top views from this lofted retreat. Vaulted ceilings, gas fireplace for chilly nights, A/C for hot summer…

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 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 Crabapple Cottage in the heart of westside Bend! The first thing you'll notice when you arrive is the enormous heritage crabapple tree in the front yard. Pull into the extra long driveway and relax. You've arrived! This sweet home is high on modern style while staying true to its vintage roots. Several kayaks and a SUP are provided too. This charming home has 2+ bedrooms (queen, queen) plus a little…