Vacation Rentals

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…

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 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 snack and…

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…

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…

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…

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.…

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…

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…

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 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 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…

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…

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…

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…

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 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... make sure you're comfortable sharing the 1 bathroom! The spacious living room is perfect for catching up with friends and family. This great home comes equipped with several instruments so you can jam at a moment's notice. You'll love having a wrap around patio/deck for…

Bungalow Blue is a charming 3 bed, 2 ½ bath home located on Bend’s popular West Side right in the heart of it all! You'll love this quintessential craftsman westside home. Just half a block off of Newport Avenue, Bungalow Blue is tucked into a quiet neighborhood. Welcome to your home just a few steps away from some of Bend’s most popular restaurants, coffee shops, bakeries, grocery, boutiques and more! Hop on…

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 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…