Last Updated January 5, 2021 1/5/2021

11 Coolest Airbnbs in Bend, Oregon

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Bend, Oregon is arguably one of the coolest cities near the west coast. There is a youthful characteristic, while a lot of the history and old appeal has been impeccably preserved. Restaurants, shops, and craft booze joints are abundant, and subtle yet funky traits can be noticed if one is paying attention. Toss in the fact that the town is a nature lover’s haven, then you have something truly special. We’ve searched Airbnbs to bring you the coolest ones in Bend.

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Ripple at River Camp Ripple at River Camp
Credit: Airbnb.com
Ripple at River Camp

Ripple at River Camp

A very modern feel is found throughout this multi-level home in Bend, Oregon. Perfect for family reunions, or just a vacation with a few close people, it’s location and presentation are impressive. What we are fond of most are the outdoor spaces such as the balcony and grilling area.

Vintage 1956 El Rey - Airstream-Like Trailer Vintage 1956 El Rey - Airstream-like trailer
Credit: Airbnb.com
Vintage 1956 El Rey - Airstream-like trailer

Vintage 1956 El Rey - Airstream-Like Trailer

Vibes from the 1950s are ever-present in this adorable metal trailer. From colorful aesthetics to the most precious overall design, we are in love. However, the location enhances the experience, as guests will have views of the stunning mountains.

The Wee Hoose The Wee Hoose
Credit: Airbnb.com
The Wee Hoose

The Wee Hoose

Both the name and the combination of old and more updated aesthetics charm guests. Relax in the simplistic abode and enjoy its proximity to some of the best features of the area. Experience the crisp clean air while rocking on the porch or bundle up after a day traversing the snow.

Garden Airstream Garden Airstream
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Garden Airstream

Garden Airstream

A real couch that belongs in a refined parlor, breakfast bar, and metal bathtub are all found within this Airstream. So basically it feels like an actual home on the inside, just quite a bit smaller. Wooden floors add warmth to the space, and the outdoor seating area is ideal on cool early spring afternoons.

Forested Artistic Cozy, Tiny House with Wildlife Forested Artistic Cozy Tiny House w/ Wildlife
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Forested Artistic Cozy Tiny House w/ Wildlife

Forested Artistic Cozy, Tiny House with Wildlife

This green tiny house is much bigger on the inside than it looks! A modern farmhouse feel flows throughout, and be aware that a little bit of agility might be needed to navigate some of the spaces. The stairs being one example! Surrounded by woods, you think you are far away from everything when actually downtown is a stone’s throw away.

Lavender Lane Farm Lodge Lavender Lane Farm Lodge
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Lavender Lane Farm Lodge

Lavender Lane Farm Lodge

With the overall feel being lodge-like, guests will be thrilled to know they are going to get the true Oregon experience when staying at this cozy split loft structure. Not only is Bend extremely close, but the town of Sisters is also as well. You must try the gluten-free treats at Angeline‘s Bakery. Tumalo has a cool food truck park and a pretty neat coffee house.

NW Modern, River, Old Mill Near Downtown NEW NW Modern, River, Old Mill near Downtown
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NEW NW Modern, River, Old Mill near Downtown

NW Modern, River, Old Mill Near Downtown

So, you can open up the living room to the great outdoors via a garage-style door. That alone earns this new edgy home “cool“ status. Basically identifying the feel of Bend, the design is rustic yet contemporary. Float the river, which is right across the street, or walk to the Old Mill District and taste some brews or cider.

The High Desert Loft - Westside Bend The High Desert Loft - Westside Bend
Credit: Airbnb.com
The High Desert Loft - Westside Bend

The High Desert Loft - Westside Bend

Lots of rustic wood, interesting tile work, and contemporary fixtures bring this loft to a modern status. From the exterior, the look is very futuristic, and a seamless blend within the super hip town of Bend. Enjoy walking to the best breweries, and restaurants in the entire area.

Cozy River Front "NEST" Cozy River Front
Credit: Airbnb.com
Cozy River Front "NEST" | Old Mill | Dogs OK

Cozy River Front "NEST"

Clean lines and interesting design come together to make one awesome loft. Four guests can comfortably stay within the out-of-the-box abode. Ascend the spiral staircase to the coziest sleeping space. And enjoy proximity to the best hiking trails and restaurants.  However, some nights guests might just want to take advantage of the deck with a grill.

Cecil House, Historic Home with a Hot Tub Cecil House, Historic Home with a Hot Tub
Credit: Airbnb.com
Cecil House, Historic Home with a Hot Tub

Cecil House, Historic Home with a Hot Tub

Anything historic is so neat! From the interesting placement of the fireplace to the seamlessly restored kitchen and wood floors, we are really feeling this Airbnb Plus. A hot tub is nestled outside, and the exterior gives off those expected craftsman attributes of homes in Bend.

Dome Sweet Dome Dome Sweet Dome ... A Must Experience
Credit: Airbnb.com
Dome Sweet Dome ... A Must Experience

Dome Sweet Dome

Is it a cabin? Is it a mathematical masterpiece? Both! The popular dome Airbnb has recently been renovated to have all of the coziness of that dwelling in the woods, but with a totally Instaworthy appeal. Take in the peaceful surroundings, and marvel over the otherworldly round shape. This is definitely a cool place to stay in a super cool area.

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