Aspen House

Cottage in Bend, OR
4.9
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 4
  • No pets
From $89 / 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.…

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…

Oak Millhouse

Cottage in Bend, OR
4.9
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 2
  • No pets
From $111 / 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…

Green Gables Estate

House in Bend, OR
5.0
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
  • No pets
From $169 / 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…

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…

  • 4 Bedrooms
  • 4.5 Bathrooms
  • Sleeps 8
  • No pets
From $264 / 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…

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…

Bungalow Blue

Bungalow in Bend, OR
4.9
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 6
  • Pets allowed
From $128 / 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…

Hygge Harmony

Bungalow in Bend, OR
5.0
  • 2 Bedrooms
  • 1.5 Bathrooms
  • Sleeps 6
  • Pets allowed
From $172 / 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…

Sunshine Daydream

Bungalow in Bend, OR
5.0
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 4
  • No pets
From $130 / 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…

Riverside Condo

Condo in Bend, OR
4.9
  • 1 Bedroom
  • 2 Bathrooms
  • Sleeps 4
  • No pets
From $70 / 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…

Columbia Spring

House in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • No pets
From $136 / night

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…

Vintage Awbrey

Cottage in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $129 / 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…

5.0
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
  • No pets
From $383 / 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…

Cascade Cottage

Cottage in Bend, OR
4.9
  • 3 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $116 / 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…

St Helens Place Cottage

Bungalow in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 4
  • Pets allowed
From $143 / 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…

Fir Millhouse

Cottage in Bend, OR
5.0
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 2
  • No pets
From $107 / 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…

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…

Cinder Cone Cottage

Cottage in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $146 / 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…

Farewell Bend Bungalow

Bungalow in Bend, OR
5.0
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
  • No pets
From $189 / 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…

North Sister Bungalow

Cottage in Bend, OR
4.9
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 3
  • No pets
From $109 / 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…