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!

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!

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.

Vintage Awbrey

Cottage in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $132 / 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!

Westside Vibes

Cottage in Bend, OR
4.9
  • 3 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $129 / 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... 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…

Look for a really nice refresh in Spring 2026! We expect to have some new light fixtures, high thread count bedding and a house general glow up :).

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!

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!

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!

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.

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!

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

Bella Bird Bungalow

Bungalow in Bend, OR
5.0
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
  • No pets
From $145 / night

The Bella Bird Bungalow is a completely renewed 1910 solar, craftsman cottage. This solar powered, 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…

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.

Columbia Spring

House in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • No pets
From $155 / 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…

Cozy modern cottage at the intersection of all things westside. Steps to all the best shops and restaurants on Galveston and Newport Ave. Mirror Pond is only 2 blocks away. You'll love the backyard fire pit, hot tub, sauna AND outdoor shower

Sunshine Daydream

Bungalow in Bend, OR
5.0
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 4
  • No pets
From $99 / 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.

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.

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!