Sunshine Daydream

Bungalow in Bend, OR
5.0
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 4
  • No pets
From $94 / night

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…

Sweet Sunshine Daydream is tucked away right on the edge of downtown Bend. Walk 1/2 a block to start your exploration of downtown restaurants, shops and more! This sweet gem is the perfect basecamp for a Bend adventure.

Green Gables Estate

House in Bend, OR
5.0
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
  • No pets
From $129 / night

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 lovely and restored historic home in Bend offers room to roam inside and out! Quiet and peaceful, tucked into the charming historic neighborhoods of downtown Bend. Curl up by one of the fireplaces or find a balcony perch and enjoy!

Cecil Sly

Bungalow in Bend, OR
5.0
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 4
  • Pets allowed
From $139 / night

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 anywhere downtown…

Cecil Sly is a Registered Historic home on a quiet treed residential block right at the edge of downtown Bend. This fully remodeled and historic home has it all. Amazing location, salt water hot tub, gas fireplace, solar panels and historic charm.

Big Lava

Cottage in Bend, OR
5.0
  • 3 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • No pets
From $119 / night

Coming soon on Nov 8th! We are so excited to host you in this beloved downtown home. Big Lava is switching management on November 8th and we can't wait to host you! Welcome to your Downtown Oasis! Big Lava is home IN Downtown Bend! Fully Furnished with 3 king beds, this sparkling home built in 2018 soars overhead with vaulted ceilings with windows that bring the outside in. Smack dab in the…

Lovely and light modern home In the heart of downtown Bend! You can't get any closer to all of Bend's downtown attractions! Tucked into a quiet corner of downtown, you'll have the best of everything at your fingertips!

Basalt Bungalow

Bungalow in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • No pets
From $99 / night

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…

You wanted a westside location and you'll get it here! The Basalt Bungalow is the perfect launch pad for your stay in Bend. Comfy beds, high thread count linens, 2 flat screen TVs, you decide if you venture out or just relax. Four bikes provided too!

Haven at River Camp

House in Bend, OR
5.0
  • 2 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 6
  • Pets allowed
From $195 / night

Newly built in 2019 with all the modern comforts of home plus more. You'll find a beautiful salt water hot tub, BBQ, fire pit on the patio and 4 cruiser bikes in the garage. Ensuite bathrooms and high thread count linens. Fireplace and a modern chef's 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…

Salt water hot tub and trails galore! Located between the Haul Road & Deschutes River trails, you will love walking, running, biking on some of Bends most iconic trails. So close to trails AND downtown Bend...welcome to the best of both worlds!

  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 6
  • No pets
From $139 / night

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…

Lovely horizon views and river peeks from this beautiful end unit home in the Old Mill. Walk to concerts, shopping, movies or just enjoy the river trail. Snuggle up by your fireplace or daydream on balcony. This is the perfect getaway.

Cascade Cottage

Cottage in Bend, OR
4.9
  • 3 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $109 / night

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…

Downtown Bend is 3 blocks from this vacation launchpad. This comfortable and modern home rises high from its historic cottage roots. You'll love having 2 flatscreen TVs, wifi, 2 bikes, hot tub and an amazing location to the river trail and downtown.

South Sister Bungalow

Bungalow in Bend, OR
4.9
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 2
  • No pets
From $99 / night

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…

A classic craftsman bungalow home IN downtown Bend. Less than a block to Jackson's Corner, 3 blocks to the river and 4 blocks to downtown Bend. This renewed bungalow home is so charming. Dedicated parking spot, yard and BBQ too! Come stay!

Riverside Condo

Condo in Bend, OR
4.9
  • 1 Bedroom
  • 2 Bathrooms
  • Sleeps 4
  • No pets
From $61 / night

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…

Great top floor condo in a riverside complex! Just 3 blocks to downtown Bend! Saunter to the river, play in the park, amble downtown...Fully furnished kitchen for cooking, 2 balconies overlooking the big park-like grounds.

Elderberry Cottage

Bungalow in Bend, OR
4.9
  • 3 Bedrooms
  • 1 Bathroom
  • Sleeps 8
  • Pets allowed
From $113 / night

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…

Tuck into this classic bungalow home...you are only 2 walkable blocks from downtown Bend at the Elderberry Cottage! Classic charms abound...snuggle up in front of the fireplace, make it a movie night on the flatscreen TV, free wifi/cable, & hot tub!

Fir Millhouse

Cottage in Bend, OR
5.0
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 2
  • No pets
From $80 / night

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…

The perfect spot for your downtown Bend stay! Located on a quiet dead-end street just blocks to the Deschutes River, Downtown Bend and the Old Mill, this beautifully restored home is the place you've been looking for.

North Sister Bungalow

Cottage in Bend, OR
4.9
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 3
  • No pets
From $99 / night

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…

A sweet craftsman bungalow home IN downtown Bend? This is it! Less than a block to Jackson's Corner, 3 blocks to the river and 4 blocks to downtown Bend. This renewed bungalow home is so charming. Dedicated parking spot, yard and BBQ too! Come stay!

Cinder Cone Cottage

Cottage in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $109 / night

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…

Cinder Cone is the perfect spot on the popular westside of Bend. Exposed wooden beams, vaulted ceilings with skylights, just 1-2 blocks from Galveston Ave restaurants, shops, cafes! Enjoy your own private hot tub and yard.

Vintage Awbrey

Cottage in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $109 / night

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…

Three blocks to the heart of downtown Bend, this vintage-modern home will be the perfect homebase for your Bend getaway. You'll find a wood burning fireplace, A/C, flatscreen/cable, TV, wifi, bikes and hot tub. You'll be set for your Bend getaway!

5.0
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
  • Pets allowed
From $181 / night

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…

Riverfront home with modern amenities in the heart of westside Bend! Outdoor hot tub, free internet, HDTV, gas outdoor BBQ, riverfront dining. Walk a block to Galveston Ave for some of Bend's best restaurants, cafes and shops! Welcome to Bend!

St Helens Place Cottage

Bungalow in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 4
  • Pets allowed
From $129 / night

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 sweetly restored cottage home in Bend offers room to roam inside and out! Quiet and peaceful, tucked into the charming historic neighborhoods of downtown Bend. Curl up by the fireplace or relax in the spacious front yard.

5.0
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
  • No pets
From $249 / night

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…

Lovely & luxe, riverfront home in the heart of westside Bend. Curl up by any of 3 indoor fireplaces and watch the river flow by. Outdoor BBQ & private river access. Walk 1 block to Galveston Ave to some of Bend's best restaurants, food carts & drinks

Khaya

House in Bend, OR
5.0
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 6
  • Pets allowed
From $199 / night

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…

Eco smart, solar powered, LEED certified home in the heart of Bend..Walk to downtown, just about everywhere! Heated floors underfoot, soaring ceilings overhead and 3 king bedrooms welcome you to your best Bend getaway yet!

  • 4 Bedrooms
  • 4.5 Bathrooms
  • Sleeps 8
  • No pets
From $155 / night

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…

Superb views from this lovely home in the heart of the Old Mill. Walk to concerts, shopping, movies, or stroll the River Trail. Grab a SUP (2 provided). Enjoy a cozy fireplace and listen to concerts from your 2 balconies. Come enjoy!

Bella Bird Bungalow

Bungalow in Bend, OR
5.0
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
  • No pets
From $122 / night

The Bella Bird Bungalow is a completely renewed 1910 craftsman cottage. This 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 cafes, restaurants and…

Sweet cottage home with modern amenities in the heart of westside Bend! Outdoor hot tub, wifi internet, HDTV, gas fireplace, gas outdoor BBQ, outside dining, bikes. Walk a block to Galveston Ave for some of Bend's best restaurants, cafes and shops.