Nature, craft beer, coffee – three great reasons to visit the city of Bend. And if you’re visiting, staying in an Airbnb in Bend, Oregon is one of the best choices you could make.
Whether you’re on a budget or if you prefer to splurge a little, there’s loads of awesome Airbnbs here that make for a lovely stay in this underrated city. Choose to stay downtown to be close to all the action or get ensconced in nature for a peaceful getaway.
No matter what type of stay you’re looking for, you’re sure to find a Bend vacation home for you. Read on for our picks of the best Airbnbs, VRBOs, and vacation homes in Bend, Oregon!
Editor’s Note: Please note that Airbnb recently made changes to their program so in this article, we are including links to other options like VRBO or Booking.com which have much lower booking fees.
- 1 Quick Answer: Best Vacation Homes, VRBOs, and Airbnbs in Bend, Oregon
- 2 15 Best Airbnbs in Bend, Oregon
- 2.1 Chili Powder Inn
- 2.2 Urban Haven in a Mid-Town Condo
- 2.3 NW Cozy Guest Suite with Private Entrance
- 2.4 Urban Studio Loft Apt (Hot Tub, HBO, Views & AC)
- 2.5 Historic Drake Park Neighborhood
- 2.6 Home Away from Home (aka Book House)
- 2.7 Cozy Up at a Nature-Inspired Boutique Studio in the Trees
- 2.8 Old Mill and River Walk Retreat
- 2.9 Historic Millhouse Bungalow #156
- 2.10 Dome Sweet Dome
- 2.11 A-Frame of Mind
- 2.12 Contemporary Home in the Sweet Spot of Downtown Bend
- 2.13 Downtown Bend Waterfront Escape
- 2.14 River Wild 19704
- 2.15 The Church
- 3 Things to Do in Bend, Oregon
- 4 Packing for Your Trip
Quick Answer: Best Vacation Homes, VRBOs, and Airbnbs in Bend, Oregon
|Our Picks||Airbnb||Book Here|
|Best Overall Vacation Home in Bend, Oregon||Dome Sweet Dome | Entire Home (2BR, 1B)||View on Airbnb|
|Best Budget Vacation Home in Bend, Oregon||Chili Powder Inn | Entire Home (1BR, 1B)||View on Airbnb|
|Best Luxury Vacation Home in Bend, Oregon||Contemporary Home in the Sweet Spot of Downtown Bend | Entire Home (2BR, 2.5B)||View on Airbnb|
|Best Vacation Home in Bend, Oregon For Couples||Cozy up at a Nature-Inspired Boutique Studio in the Trees | Entire Home (1BR, 1B)||View on Airbnb|
|Best Vacation Home in Bend, Oregon For Groups||Downtown Bend Waterfront Escape | Entire Home (3BR, 2.5B)||View on VRBO|
15 Best Airbnbs in Bend, Oregon
Chili Powder Inn
Type: Entire Home (1BR, 1B)
Location: Larkspur, just outside of the Old Farm District
For an affordable stay that doesn’t compromise on style or amenities, check out this lovely vacation home in Bend that’s sure to delight.
Located in a residential neighborhood just outside of downtown, the Chilli Powder Inn is perfect for solo travelers, couples, or small families. The home is spacious and airy, with enough space for four people thanks to the pull-out couch in the living room.
The open floor plan means an integrated space that combines the living room, the dining area, and a kitchenette. Cute decorative touches ensure nothing looks drab or basic here, and wooden accents add a touch of rustic charm.
The sliding wooden barn door leads to the master bedroom which is outfitted with a queen-size bed.
A stay here means easy access to nearby hiking and biking trails, plus some cool breweries and cafes in the vicinity.
Why We Love It: Stylish and comfortable stay at an affordable price tag.
What Past Guests Have Said: “Spacious and comfortable, perfect for an overnight trip (or longer). Very clean and easy communication. Would definitely stay again and recommend to others.”
“Good place to stay if you’re in Bend for the weekend!”
“We had a perfectly splendid time! Adorable space with everything we needed and close to the mountain. The bed was comfortable and the coffee was delicious. Overall a great experience!”
Urban Haven in a Mid-Town Condo
Type: Entire Home (1BR, 1B)
Location: Mid-Town, 2.5 miles from downtown
This vacation rental in Bend, Oregon is billed as an “urban haven” and it certainly lives up to its name! Part of a single-story condominium complex, this modern loft-style apartment has a Mid-Town location so you’re not too far from the heart of the action in Bend.
This home is definitely pleasing to the eye, with white walls and interesting features that give the space some personality. Exposed brick walls, quirky artwork, cool rugs all give a touch of style. The front of the home holds the living area with its comfy couch and chair, and further back lies the fully-functional kitchen that has some bar seating.
The bedroom here is super spacious and pretty, making it a great place to rest your head after long days of exploring.
For some fresh air, head to the outdoor patio where you can get the fire pit going to stay warm.
Why We Love It: Modern, well-decorated apartment for an awesome stay.
What Past Guests Have Said: “Great location, super clean, and had everything we needed!”
“Hosts offer a very clean and cozy space. I would definitely stay there again next time I’m in Bend.”
“The home is cozy and the perfect place to come back to after a day of adventures! They are fantastic hosts and did a great job with the place and communicating”
NW Cozy Guest Suite with Private Entrance
Type: Entire Home (1BR, 1B)
Location: River West
If a cute and cozy spot for two is right up your alley, then this is the vacation home in Bend, Oregon for you. This sweet spot is located in Bend’s Westside, and you’ll be in close proximity to restaurants and breweries.
Head up the spiral staircase to get to the entrance to this tiny-home-inspired apartment. The front area has armchairs, a small dining table, and a handy kitchenette nestled in the corner. Beyond the wooden partition, you’ll find a queen-size bed. There’s also a bathroom tucked away.
Grab some fresh air by spending time on your private balcony and if it’s too cold, simply fire up the gas fire pit.
Why We Love It: Small and cute apartment that’s ideal for couples.
What Past Guests Have Said: “Very cute, cozy guest unit with great amenities! Tons of restaurants and breweries in walking distance, and outdoor activities! We will definitely be looking at this unit for our next trip to Bend.”
“What a cute and cozy place! Great hosts. Perfect for a weekend trip to Bend.”
“Great, centrally located place! Very well maintained and highly recommended. Would stay again without hesitation.”
Urban Studio Loft Apt (Hot Tub, HBO, Views & AC)
Type: Entire Home (1BR, 1B)
Location: Westside, near NW Portland Ave
This vacation rental in Bend, Oregon is just brimming with personality! Suitable for people looking for a quiet retreat in the city, this remodeled loft-style studio apartment provides a comfortable stay with everything you need.
Wooden accents, funky furniture, and patterned rugs make up the living room which offers lots of space to relax and lounge after a busy day out. Tucked away in the back corner, there’s a fully-functional kitchenette plus some bar seating that looks out to the backyard and beyond.
In the loft space upstairs is the bedroom where you can relax in the queen-size bed.
With this stay, you’ll also have access to some communal facilities which include a hot tub. Win!
Why We Love It: Funky loft-style apartment with all the amenities you need.
What Past Guests Have Said: “Alex was a great host and the place was Super beautiful and warm. 10/10 would love to rent with them again!”
“This is truly such a neat spot! Cozy, unique, and groovy! We especially loved sitting at the beautiful kitchen counter and watching the sunset. Very comfortable bed (with awesome skylight), plenty of books, loads of natural light, and a great stereo set-up. We loved all of the personal touches, and felt very at-home. The space was quiet, even with neighbors in the same building. I’d highly recommend to anyone visiting Bend and will certainly be back!”
Historic Drake Park Neighborhood
Type: Entire Home (1BR, 1B)
Location: Drake Park
A warm and inviting home awaits you at this Bend vacation home that’s located near Drake Park. This one-bedroom apartment works well if you’re traveling alone or as a duo.
This vacation rental has an eclectic feel that is nonetheless charming. The living room, with its mismatched furniture, is a cozy place to hang out while the kitchen looks sleek and high-tech with its white cabinetry and steel appliances. There’s loads of space in the kitchen and dining area, so it’ll be a pleasure eating in during your stay.
Behind a rustic wooden barn door lies the spacious bedroom that has more than enough room for two. Plus, the bathroom is simply massive!
Best of all, you’re just minutes from the riverwalk and downtown.
Why We Love It: Charming and spacious home, suitable for two.
What Past Guests Have Said: “Cindy and Greg’s place was absolutely perfect. The location was perfect and the space was very clean and had all the amenities you would need for a vacation. We absolutely loved our stay!”
“This was my second time staying here. We are so glad we did with getting lots of snow on our second day. It was so convenient to be able to walk to the park or downtown. We had everything we needed for a comfortable stay.”
Home Away from Home (aka Book House)
Type: Entire Home (1BR, 1B)
Location: Westside, near Harmon Park
Calling all bookworms! There’s no better Airbnb in Bend, Oregon for you than this one… aptly named Book House. This artsy, quirky home is filled with our favorite friends: books.
Floor-to-ceiling bookshelves line the common areas, overflowing with books covering tons of topics. Believe me, you won’t run out of reading material while you’re here! And thanks to large windows, you’ll get lots of natural light streaming in to make it easy to devour these books.
This Airbnb feels like a lived-in space, with comfortable touches that make it feel like your own home. Make a cup of tea and lounge in the living room with a book or get some pages in while you’re waiting for your meal to be done.
If you want, bring your book into the cozy bedroom and get some nightly reading in before going to bed. Aside from the bedroom, the home can also accommodate two more people in the pull-out futon in the living room.
Why We Love It: Cozy, artsy home that’s ideal for book-lovers.
What Past Guests Have Said: “This spot is a gem! Unique and funky and cozy. The house feels comfortable and is filled with books to explore. Perfect walking distance to some of our favorite eats and a quick walk to old town Bend and local parks. We will be back!!”
“This is our fourth time staying at the book house and we love it. It’s such a great space and the location is convenient.”
Cozy Up at a Nature-Inspired Boutique Studio in the Trees
Type: Entire Home (1BR, 1B)
Location: Near First Street Rapids Park
Relax and unwind at this nature-inspired studio near First Street Rapids Park. This lovely vacation home is a great spot for a romantic getaway in Bend, Oregon.
While it is a studio, it is absolutely massive, with more than enough room for you to feel comfortable and relaxed. There’s everything you need for a great stay: a fully-equipped kitchen with all the amenities, a dining table for two, a massive king bed, and a cozy living area that’s tucked away in a corner.
Throughout the home, there are nature-inspired touches such as the artwork, decorative accents, and hanging plants. Plus, thanks to the huge windows, you’ll get loads of natural light in here.
Why We Love It: Cozy, well-decorated studio that’s not too far from downtown.
What Past Guests Have Said: “We had a two night stay at this Airbnb and we wish it would’ve been longer! The space is very well accommodated and the ambiance is very cozy and appealing, also very well kept and clean. Ryan is a wonderful host and we look forward to staying at this Airbnb again!”
“I had a great stay at Ryan and Katie’s place. They were warm and welcoming and made sure I had everything I needed. I highly recommend this spot, beautiful location, close to everything and literally a stones throw from one of the Deschutes Rapids parks and walking trails. The studio was well appointed and cozy with everything you could need for a short or long term stay.”
Old Mill and River Walk Retreat
Type: Entire Home (1BR, 1B)
Location: Across from Farewell Bend Park
Located over the host’s garage, this Airbnb in Bend, Oregon is miles away from what you’d think a garage home would look like. Occupying the entire second level, this guest house is simply lovely and will offer you an amazing stay.
Bright and airy thanks to the numerous windows, this open-plan home has spaces that just flow into each other. The comfy couches grouped together face the kitchen, making it easy to still hang out together while cooking up a storm. Filled with white cabinets and shiny appliances, the kitchen is an absolute delight and has everything you need for self-catering. There’s also a small dining table in the corner where you can enjoy your meals.
The four-poster bed in the bedroom is ultra-comfy, and you’ll have a huge en-suite bathroom as well.
On top of all that, you also have a private deck – the perfect spot for your morning coffee!
Why We Love It: Inviting and well-designed home in a quiet neighborhood.
What Past Guests Have Said: “This is a really nice place. The pictures are a good representation of what you get. The vaulted ceilings make for a spacious feel. The dog friendliness was a 10 out of 10. The location is great, 10-15 minute walk to Old Mill shopping for us. If you’ve got your dogs there’s a small park just down the street and the waterfront park is about a 2 minute walk. Bed is comfy for my taste, a bit on the firm side. It has large windows front and back for lots of great light. Christina was also kind enough to make it snow for our trip which was appreciated.”
Historic Millhouse Bungalow #156
Type: Entire Home (1BR, 1B)
Location: Jefferson Place, a few blocks from Jackson’s Corner
This quietly elegant home has a mix of both rustic and modern, making for a charming stay in a central location. With one bedroom and one bathroom, this vacation home in Bend, Oregon is a top choice for couples holidaying in the city.
Originally a millhouse, this historic bungalow has been remodeled into the perfect vacation home. The interior just gleams with wood, from the hardwood floors to the wooden cabinetry and panels around the house. Off-white walls and furnishings brighten up the space, along with colorful accents and pops of patterns here and there.
The rooms here are all separated by function. Lounge about in the living room, get your chef’s hat on in the beautiful wooden kitchen, and tuck in to delicious meals at the cozy dining area.
Here, you’re sure to get a good night’s rest in the well-appointed bedroom with its plush bed and high-end beddings. What’s more, there’s a clawfoot tub in the bathroom for the ultimate relaxing bath!
Why We Love It: Gorgeous bungalow that’s ideal for couples.
What Past Guests Have Said: “Tom & Cheryl’s home is amazing and the perfect location. It’s a quiet neighborhood but minutes to the downtown area and the river. We felt right at home staying there.”
“This is a great space that is ideally located in Bend, near the river, hiking trails, breweries, and downtown areas. The space is as shown in the pictures and was actually a bit larger than expected. Highlights included the bathtub, the kitchen, the gas fireplace, and the super comfy bed. I’d definitely stay here again!”
Dome Sweet Dome
Type: Entire Home (2BR, 1B)
Location: First-on-the-Hill, off Century Drive
Without a doubt, this has to be one of the best vacation homes in Bend, Oregon. Situated in the First-on-the-Hill neighborhood on a private lot, this geodesic dome will be an unforgettable stay!
This vacation rental is for you if you want something a bit more unique and peaceful. You’ll be nestled in nature in this cool structure that actually offers tons of comfort and amenities on the inside.
You’ve got everything you need here for a cozy retreat: a lovely living room with a fireplace, a small kitchenette, a dining table, and two bedrooms. Plus, a cool feature: the second floor is floating!
With this dome home, you’ll be close to biking trails and in a location secluded enough that you can see the stars from inside the dome at night!
Why We Love It: Unique and charming stay that’s close to nature.
What Past Guests Have Said: “Truly special. The location just cant be beat, halfway between food and Bachelor. We’re very much looking forward to next years trip.”
“The dome is so cute and fun! Perfect little getaway”
“The dome was everything I was looking for! Thanks Denise!”
A-Frame of Mind
Type: Entire Home (2BR, 1.5B)
Location: Near Deschutes River Woods
A peaceful getaway in nature awaits you at this vacation home in Bend, Oregon. This is the place for you if you prefer to stay outside of downtown and have a more nature-focused holiday. That said, you’ll still only be a 10-minute drive from downtown Bend.
This A-frame home maybe about 50 years old but it’s functional as well as stylish. The interior exudes modern, country vibes. There’s wood paneling everywhere and touches of greenery that bring the outside into the space.
The living is a cool spot to hang out with its L-shaped couch and fireplace. Tucked away at the back is a fully-stocked kitchen so that you can cook all your own meals without any hassle. Upstairs, the home has two bedrooms which can accommodate up to four people in total.
Besides those, there are other cool features in this home like the little window seating nestled in a corner, the lounge space with vinyls and musical instruments, and the outdoor deck where you can take in the fresh air.
Oh, and did we mention the hot tub?
Why We Love It: Cozy, A-frame home for a nature-centric getaway.
What Past Guests Have Said: “This place was awesome. It felt like a home away from home.”
“Mike’s place is everything you want it to be and more. Super cozy, welcoming and well decorated, plenty of space, perfect amenities (the hot tub was amazing), and such an incredibly convenient location! I only wish we’d had more time here. Totally worth the price, we will definitely be back and will recommend to family and friends.”
“Super cute and close to in town, but not too far out! Quite and peaceful, totally worth the price. Definitely reccomend!”
Contemporary Home in the Sweet Spot of Downtown Bend
Type: Entire Home (2BR, 2.5B)
Location: NW Newport Ave, near the Deschutes River
This Bend vacation home offers both the serenity of staying in a quiet neighborhood while being within walking distance to downtown – a sweet spot, indeed!
This two-bedroom stunner is decorated in a contemporary style that’s very pleasing to stay in. Large windows and white walls give the home a sense of space and wood accents in the furniture give it a warm vibe.
Get warm by the fireplace in the comfortable living room, try new recipes in the spacious kitchen, and sit down for a lovely dinner at the wood dining table. There’s also a patio with seating and a BBQ, if you want to spend time outdoors.
You’ll be charmed by the bedrooms which are an oasis of relaxation, decorated in white and muted colors. There are bathtubs in both bathrooms so be sure to get a relaxing soak in during your stay!
Why We Love It: Contemporary home that’s stylish, great for couples or families.
What Past Guests Have Said: “Such an amazing space! The house was incredibly clean and comfortable. Linda did a great job communicating and outlining and details we may need. The house is in a really great location too! We loved our stay.”
“Wonderful spot within walking distance to downtown Bend. Modern decor and spotlessly clean. We’ll definitely be back next time we’re in Bend!”
Type: Entire Home (3BR, 2.5B)
Location: Near Brooks Park
For a family or group vacation in Bend, this vacation home facing Mirror Pond is an awesome place to stay. With three bedrooms, there’s enough space here for up to eight people and you’ll have the whole massive house and backyard to yourself.
The bright and cheerful home has tons of natural light, thanks to the huge windows around the house. Hang out together in the living room or second den, both comfy places for everyone to gather.
The fully-stocked kitchen has a professional range and room for everyone to come and pitch in for the prep. The bedrooms are simply furnished and comfortable.
The backyard has outdoor seating and a BBQ… plus direct access to the river! Make use of the paddleboards and tubes and send some time out on the water.
Overall, this is a great stay for groups!
Why We Love It: Massive home with all the amenities and direct river access.
River Wild 19704
Type: Entire Home (3BR, 3.5B)
Location: Century West
Nestled among the trees, this lodge-style home is country living at its best. Call your friends or family along as this home has three bedrooms that can sleep a total of six people.
Located just steps from the Deschutes River trail, this spacious house combines rustic charm with all the comforts of home. The interior boasts a vaulted ceiling, loads of wood, and lush leather sofas. Thanks to the large windows throughout the home, you’ll have awesome views and tons of natural light streaming in.
The rustic theme continues in the bedrooms which are well-appointed and ultra-comfy.
The home has an awesome wrap-around deck which is a lovely place to have dinner or enjoy some drinks. Don’t forget to have a soak or two in the oversized hot tub!
Why We Love It: Charming rustic home with tons of space and amenities, including a hot tub.
What Past Guests Have Said: “You will absolutely love the windows and the porch. It’s beautiful nestled among lots of trees. I loved the location and private hot tub.”
“This is a very spacious home with beautiful decor. It had the best equipped kitchen of any place we’ve ever rented. And everything was sparkling clean. We especially liked the convenience of being able to walk straight down the hill to the Deschutes River Trail. Also liked the closeness to town. We recommend it highly.”
Type: Entire Home (3BR, 3B)
Location: Near downtown Bend
As you might’ve guessed from its name, this vacation home in Bend, Oregon was transformed from a church into a gorgeous vacation home. Located near downtown, you’ll just be minutes from the shops, restaurants, and bars in the center of town.
This vacation rental is absolutely huge and can comfortably sleep up to eight people in its three bedrooms. The ground floor holds the common areas which all flow into each other in the open space. Relax on the many couches in the living room, cook up some grub in the open kitchen, or just chill out by the dining table. There’s certainly room for everyone!
Head up to the second floor to access the bedrooms which are comfy havens for rest and relaxation. There are also two more lofts with twin beds so everyone has a place to sleep.
If that’s not enough, there’s also outdoor space for you and your group. There’s a patio with seating, a grill, and fire pit for your use.
Why We Love It: Church-turned-home that’s just perfect for families or groups.
Things to Do in Bend, Oregon
Need help planning your itinerary in Bend? Check out these awesome Airbnb experiences!
- Black Magic – Home Coffee Roasting: Coffee-lovers, here’s your chance to learn how to roast your own beans at home!
- Uplifting Meditation and Healing Event: Relax and find your inner peace at this event by the Blissful Heart Wellness center.
Packing for Your Trip
Before you take off for your trip, check out our travel gear page to make sure you don’t miss out on anything important!
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