Vacation Rentals

Newly built in 2019 with all the modern comforts of home plus more. Salt water hot tub, BBQ and fire pit on the patio. Ensuite bathrooms and high thread count linens. Fireplace and a modern kitchen. This home has everything you need and want in your modern Bend stay. You'll love feeling like you're in the woods and in downtown Bend all at the same time. There are walking paths that intersect…

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…

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 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…

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…

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 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 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…

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 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 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 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 or a…

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…

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…

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 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 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…

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 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 the Riverside Condo! Cozy, top floor 2-bed, 2-bath condo in a riverside complex just 2-3 blocks from Downtown Bend! Saunter to the river, play in the park, or cruise to downtown Bend. You'll love having a fully furnished kitchen for cooking, gas fireplace, A/C, and 2 balconies overlooking the common courtyard! DOWNTOWN LOCATION The River Retreat Condo is only a skip to downtown Bend! With the Deschutes River, Bend River…