Oak Millhouse

Cottage in Bend, OR
4.8
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 2
  • No pets
From $90 / night

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…

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.

Farewell Bend Bungalow

Bungalow in Bend, OR
5.0
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
  • No pets
From $149 / night

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…

Excellent downtown Bend location just steps to Jackson's Corner, the Old Mill and the surf wave. Historic charm and a clean, modern vibe, this lovely home has a king suite that takes up the whole upper floor and 2 main floor queen bedrooms. Welcome!

South Sister Bungalow

Bungalow in Bend, OR
4.9
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 2
  • No pets
From $109 / 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!

5.0
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
  • Pets allowed
From $261 / 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!

Basalt Bungalow

Bungalow in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • No pets
From $115 / 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!

Fir Millhouse

Cottage in Bend, OR
5.0
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 2
  • No pets
From $90 / 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.

Hygge Harmony

Bungalow in Bend, OR
5.0
  • 2 Bedrooms
  • 1.5 Bathrooms
  • Sleeps 6
  • Pets allowed
From $166 / night

Welcome to Hygge Harmony, a 1927 westside bungalow that delivers big on style! This light and bright home has two bedrooms (king, king), sleeper sofa (queen) and one full bathroom and one extra shower. You'll love the large bedrooms which are so rare for bungalow homes. Snuggle up in front of either of the 2 gas fireplaces in the master bedroom and kitchen, and the luxury of a hot tub! We do…

Fantastic 2 bedroom home with luxury styling! Vintage chandeliers, cozy fireplaces, Viking range...you'll be at home in this gem! Just steps to all 10 Barrel, the food cart lot, all the restaurants and shops on Galveston. This is the heart of Bend!

Cinder Cone Cottage

Cottage in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $126 / 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.

5.0
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
  • No pets
From $384 / 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

Bungalow Blue

Bungalow in Bend, OR
4.9
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 6
  • Pets allowed
From $150 / night

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…

Sweet cottage home with modern amenities in the heart of westside Bend! Two fireplaces, free wifi, window A/C in summer, gas outdoor BBQ, outside dining, bikes. Walk a block to Newport Ave for some of Bend's best restaurants, cafes & shops.

Green Gables Estate

House in Bend, OR
5.0
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
  • No pets
From $180 / 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!

Strawbale Basecamp

House in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 4
  • Pets allowed
From $90 / night

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,…

Spacious and stylish straw bale home in Bend's historic district. Just steps from Mirror Pond float location in Drake Park! You can't get any closer to the center of Bend...A great location for your month or more in Bend!

Elderberry Cottage

Bungalow in Bend, OR
4.9
  • 3 Bedrooms
  • 1 Bathroom
  • Sleeps 8
  • Pets allowed
From $126 / 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!

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.

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.

Bernhard Justice Bungalow

Bungalow in Bend, OR
5.0
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
  • No pets
From $161 / night

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…

Historic craftsman home with modern amenities in the heart of downtown Bend! Hot tub, wifi internet, smart TVs, gas fireplace, gas outdoor grill, dining. Walk a block in just about any direction to restaurants, cafes and historic neighborhoods.

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.

  • 4 Bedrooms
  • 4.5 Bathrooms
  • Sleeps 8
  • No pets
From $250 / 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!

Sugar Plum Loft

House in Bend, OR
5.0
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 4
  • No pets
From $80 / night

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…

You'll adore this brand new loft in the heart of Bend. Walkable to coffee, dinner, Mirror Pond and more. This home shows off its space with soaring ceilings, spacious king bedroom and private balcony. You'll love this spot for your month + in Bend!

Aspen House

Cottage in Bend, OR
4.9
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 4
  • No pets
From $99 / night

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 the Aspen House! You'll love this modern cottage with cozy charm and global flair! Bring your adventurous spirit and embrace your amazing location in downtown Bend. Saunter in any direction and you’ll find lots to do in downtown Bend!

  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 6
  • No pets
From $160 / 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.