Westside Downtown Bend

Heart of Bend

Bungalow in Bend, OR
4.9
  • 3 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $129 / night

Enjoy playing around Bend (hiking, Ale Trail, SUPs, mountain biking, skiing, shopping, l) and retreat back to Bend's premier River West neighborhood for a peaceful night sleep. Heart of Bend is kid & pet friendly. Fully stocked kitchen. Modern feel. And a fenced in private patio for relaxing. Heart of Bend is a charming 3 bed, 1 bath home located on Bend’s popular West Side right in the heart of it all!…

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…

Hygge Harmony

Bungalow in Bend, OR
5.0
  • 2 Bedrooms
  • 1.5 Bathrooms
  • Sleeps 6
  • Pets allowed
From $109 / 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…

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…

Federal

House in Bend, OR
5.0
  • 3 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $94 / night

Welcome to The Federal House! This classic Westside Bend home is fully furnished for your Bend getaway for summer or winter activities! Located between downtown and the very popular Galveston and Newport Avenues. This is one of the best locations in Bend and a prime location to explore all Bend has to offer! DOWNTOWN LOCATION Just two blocks from 10 Barrel Brewing and Sunriver Brewing, and only a 15-minute stroll to downtown…

Westside Vibes

Cottage in Bend, OR
5.0
  • 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…

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…

Hillside Loft

Studio in Bend, OR
5.0
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 2
  • No pets
From $65 / night

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…

Elderberry Cottage

Bungalow in Bend, OR
5.0
  • 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…

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 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…

Crabapple Cottage

House in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • No pets
From $94 / night

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…

Bungalow Blue

Bungalow in Bend, OR
4.9
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 6
  • Pets allowed
From $103 / 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…

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…

Columbia Spring

House in Bend, OR
5.0
  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • No pets
From $169 / 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…

Cascade Cottage

Cottage in Bend, OR
4.9
  • 3 Bedrooms
  • 1 Bathroom
  • Sleeps 6
  • Pets allowed
From $115 / 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…

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…

Sugar Plum Cottage

Cottage in Bend, OR
4.9
  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 4
  • No pets
From $115 / night

This sweet cottage is a completely refreshed 1910, craftsman bungalow. Welcome to the Sugar Plum Cottage. This fully furnished home has been head to toe remodeled in 2023 and has 1 bedroom (Queen), 1 bathroom and a Queen pull out sleeper sofa. Snuggle in and enjoy the very best Bend has to offer. Just 1 block from the delicious food cart lot and all of the cafes, restaurants and breweries on Galveston.…