Vacation Rentals

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 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 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 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…

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…

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…

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 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…

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 the Riverfront Retreat. A stunning riverfront hide-away on the super popular westside of Bend. Perched above the river, you'll love year round views. The wildlife varies by the season, from fun and silly river floaters in summer to serene birds in winter. You can enjoy river life from both inside and outside this lovely home. Food carts, 10 Barrel Brewing, other great shops and restaurants are only a couple blocks…

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…

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…

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…

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…

Welcome to Columbia Spring in the heart of westside Bend! This sweet home is high on modern style while staying true to its vintage roots. This charming home has 2 bedrooms (king, queen) with one full bathroom. This is a spacious 2 bedroom home and there are numerous sitting areas for relaxing, playing games or getting some work done. Don't miss the backyard fire pit, hot tub, sauna AND outdoor shower. DOWNTOWN…

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 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 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,…

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…