Whether you go paddling the crystal-clear waters of the famous Deschutes River or heading out to ski the powdery white slopes at Bachelor, your Bend vacation also needs a cozy place to relax at the end of the day! If you are planning a vacation at Bend Oregon there are a number of accommodations no matter what your budget or need may be. For your hassle-free and reliable holiday experience, we bring you these gems from a host of Mill cabins, condos, and cottages in the Old Mill District of Bend. Home to action, there is plenty to offer here. Check out the best Vrbo accommodations in Bend, and book yourself a pleasurable holiday.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 16, 2025.
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1. Riverfront lodge in a picturesque setting (from USD 792)
Boasting a space of 5,000 square feet (464.52 square meters), this lodge is the best choice for large groups. There are 10 beds inside, comfortably accommodating 14 people, and you can also find a gourmet kitchen with everything you need to prepare delicious meals for everyone. Additionally, there are seven televisions and four gas fireplaces outside, so you and your companions will always be warm and comfortable while watching movies.
The outside area is just as fantastic. This lodge is nestled in a picturesque setting, with a river right out front. Because of this, you might be inspired to go on a hike and immerse yourself in nature. When you’re done hiking, come back to the lodge and soak in the hot tub to relieve your sore muscles.
Top guest reviews
Location:
location is great for local restaurants and downtownwhat a great house and locationgreat location comfortable house great kitchen and common area for socializingoutstanding our favorite place to stay in central oregonnice location close to skiing hiking restaurants and townRead more reviewsAmenities & Room:
it has lots of sleeping space and a great kitchenclose to downtown great rooms/beds and amazing view of the riverthe kitchen was extremely well stocked
2. Charming house in the heart of the West Side (from USD 550)
This 2,407-square-foot (223.62-square-meter) house is wonderfully located in Bend. It’s in the West Side, a popular section of the city, and that means many iconic attractions are nearby. For this reason, you might be interested in visiting a few tourist sites, such as Old Mill District, Drake Park, the Des Chutes Historical Museum, and Pilot Butte State Park.
After a long, tiring day, return to this house to relax and unwind. The kitchen is fully equipped, so preparing gourmet meals should be a breeze. Before going to bed, you can watch a fun movie on the television or play a few rounds of games in the game room. If you’re travelling with children, there are toys available for them.
Top guest reviews
Host:
the owners are lovely and accommodatingthe host was easily accessible and flexibleproperty manager super nice and responsivethe owners are very responsive to any issue and the house is well equippedLocation:
great house in a great locationgreat house and great location for a gatheringgreat location walking distance to great places to eat + drinknot a bad walk to the river or downtown eitherthis house was amazing it is such a great locationCleanliness:
this house was very clean well stocked and comfortablewas clean and within walking distance to most of what we were wanting to dothe home is in an great location and was very cleanRead more reviewsAmenities & Room:
the beds were comfortable and the outdoor jacuzzi was perfect after a day of skiingsmall bedrooms with comfortable bedsplenty of room well stocked and super convenient
3. Modern house with stunning views of the Deschutes River (from USD 412)
Sitting on a woody bluff, this modern house boasts stunning views of the Deschutes River and Pilot Butte Creek. For this reason, you might want to lounge on the wraparound deck, enjoying the scenery around you. There’s also a gas grill on the deck, so you can have a cookout with your companions.
The inside is just as marvellous. The kitchen is furnished with all the essentials, and a television and high-speed WiFi (around 500+ Mbps) are also provided for your entertainment. Since there are four beds in the bedrooms, up to eight people can stay here, so feel free to bring your family or friends along. Up to two dogs of any size are welcome as well — you only have to pay the pet fee of 100 USD.
Top guest reviews
Host:
owner was very responsivethe oven wasn’t working but the owner responded quickly and resolved the situationsuzie was a great host we'll be backLocation:
property was beautiful perfect location to shops food and recreationCleanliness:
the house was clean and comfortable with plenty of room for six adultsRead more reviewsAmenities & Room:
enjoyed the large deck and comfortable bedroomsstocked kitchen truly better than any other vrboi have ever stayed in
4. Cosy house for four in a historic location (from USD 166)
This house was originally built in 1925, and though it has kept its historic charm, it’s now been renovated to include modern amenities. There’s air conditioning and a fireplace, so you can keep the temperature inside to your liking. WiFi access and cable television are provided, allowing you to have movie marathons during your stay. When you get hungry, cook something delicious in the well-equipped kitchen.
This rental is situated in the historic Old Town section of Bend, so you can find many iconic attractions in the area. Some of the closer ones include Old Mill District, Deschutes Brewery, and the Deschutes Historical Museum. Other places worth visiting are Pilot Butte State Park and Drake Park.
Top guest reviews
Host:
the owner/property manager colleen was very kind and responsive to any needs we hadthe owner was very responsive and quick to help with the one small hiccup we hadLocation:
a super cute house in a great locationthe location of this house is amazing quick walking distance to downtown and to old millgreat location close to walking to restaurants on the main street of bendjust a short walk to downtown or to the mill - it was perfect for our staywe enjoyed staying somewhere that we could walk out our door to access groceries restaurants shopping and exerciseCleanliness:
everything was clean and looked fantasticthe house was very clean and had everything we needed for our stayeverything was perfect -- clean comfortable well designed with a small secure fenced backyard area for our dogthe place is very clean comfortable and in a great locationRead more reviewsAmenities & Room:
there are even funny old cook books that made for hilarious reading at the breakfast table
5. Beautifully appointed bungalow for five close to everything (from USD 181)
This charming bungalow is centrally located in Bend, which means it’s close to everything — especially shops, restaurants, and local attractions. Because of this, you can easily explore Bend and see everything this city has to offer. Some of the places you should include in your itinerary are Deschutes Brewery, Tower Theater, and Drake Park.
This house is also beautifully appointed, so you’ll always be eager to come back here to relax. Feel free to whip out gourmet meals in the kitchen instead of buying something from a restaurant. If you’re bored, turn on the television, connect to your preferred streaming service, and pick something fun to watch.
Top guest reviews
Host:
hosts are very helpfulthe owners had many thoughtful niceties throughout the homecheck in was super easy and the hosts were availableLocation:
this was really cute and in the perfect locationit’s in an amazing location close to everythingsuper short walk to the river walkvery comfortable quiet and the perfect location between old town and mill districtgreat location beautiful property easy people to wonderful withCleanliness:
it was very clean and very well-stocked with anything you neededRead more reviewsAmenities & Room:
fireplace and space heaters kept the house warm and comfortablebeds were super comfy and they had everything you needed in the kitchenbeds and linens are comfortable (firm mattress if that matters to you)loved the gas fireplace heated bathroom floors and the option to heat the bed mattressesthere is a nice lawn area and outdoor table and chairs
6. Gorgeous cottage right in front of the river (from USD 623)
This 1,200-square-foot (111.48-square-meter) cottage is located right on the Deschutes River. For this reason, you’re free to engage in all kinds of exciting activities when you stay here. You can go for a refreshing swim, try your hand at fishing, or operate a paddleboard or a kayak. If you don’t like to exert too much energy, you can sit by the fire pit instead, making s'mores while enjoying the view.
The interior of the cottage is just as fantastic. There’s a fully equipped kitchen for your dining needs, as well as a cosy living area with high-definition television. High-speed WiFi — around 500 Mbps — is also available, so you can stream movies without worrying about lags. The bedrooms also have their own televisions, so you can watch something from the comfort of your bed.
Top guest reviews
Host:
jackie is an amazing and most welcoming hostthe hosts were amazing as well we will definitely be backloved the access that the owner provided to bikes sups and kayaksthe house is well equipped and the host makes sure you have everything you needour hosts were so generous and added many personal touches really blew us awayLocation:
wonderful location on the rivereasy walk to downtownloved that we could walk to all the great places bend has to offerwalks along the river walks to downtown for wonderful eateriesCleanliness:
this property was very clean and was just as describedthe house is clean beautiful and in the perfect locationRead more reviewsAmenities & Room:
everything about this cottage is perfect; location furnishings decor and has a fully stocked kitchen
7. Cute cottage for four (from USD 211)
Tradition meets modernity at this one of its kind accommodations! A cottage which once housed mill workers, today offers modern amenities like a smart TV, washer/ drier, refrigerator, and even a work station desk if you wish to bring work home. The master bedroom has a queen-size bed and an attached private bathroom, while the second bedroom has a queen size bed and access to a beautiful yard. High-speed Wi-Fi is available for use throughout your stay. Cute also offers a host of activities for winters and summers alike. If you are on a budget but do not want to compromise on basic amenities, look no further than this beautiful property.
Top guest reviews
Host:
our dog loved going downtown and also had a good time hikingwe had a lovely stay and appreciated all the attention to detailnice side yard with table and pationice home and location which served us all (2 couples) very well during our time in bend for the conference we attendedthis home faces the morning sun, which is an total energezier for usLocation:
it is a great location, nice bike to get around on, very clean and well thought outwe loved staying in this cozy little house near downtownshort walk to downtown, large garage to store your bikes, skis, etclandlord was simply the bestonce again we enjoyed the cute saginaw home and locationCleanliness:
great location, clean house, pet friendly w/ fenced backyardRead more reviewsAmenities & Room:
2nd bedroom had no drawers for clothes but bathroom had extra storage so it workedcomfortable beds, newer furnishings and nice touches like lovely soaps and shampoosair conditioner really helped in the heat while we were there, we were surprised how the one unit kept the house comfortablepat is easy to workample parking, roomy digs and great location
8. River-side contemporary cottage (from USD 378)
This riverside cottage is located in the historic Park section of Bend, and happy to be out of the limelight. Nestled in the lap of mother nature and offering a fully furnished accommodation with gas barbecue, there is even an additional room available in the main building, if needed. The hosts do mention that this property should not be considered if you travel with toddlers.
Top guest reviews
Host:
our host was greatshe even tracked me down to let me know i had left a couple of items before i left town and had them all ready for me when i arrived back at the housevery well appointed with all household necessities you could think ofneighborhood boasts many old, beautiful homes registered as national historic sitesbut everything else was greatLocation:
a very peaceful oasiseasy walk through drake park to restaurants and shopsexcellent location convenient to downtownnice location, bikes were a plusthe bikes, paddle boards and inner tubes provided enhanced the visitCleanliness:
loved the peaceful private courtyard and lovely apartmentloved the place and the effort of the ownereverything was clean, smelled great, and super close to everythingneat, clean, bright, efficient cottage in quiet old town bend neighborhoodthe cottage was exceptionally clean and had anything you would want for a great vacationRead more reviewsAmenities & Room:
everything as advertisedthe beds are comfortable and the place is so relaxingthe kitchen was the best stocked kitchen of any rental i'd ever been hadeverything was as advertised and in perfect working orderthe only thing we needed was more time to stay :)
9. Beautiful budget house for two (from USD 212)
With a loft sleeping area, sleeping is like floating in the air. With all modern amenities such as clean linen, washer-dryer facility, air conditioning, and high-speed internet, the place offers a simple, yet beautiful holiday. It is ideal for backpackers, solo travelers, and honeymooners. It is not hard on the wallet and yet makes way for a cozy stay from check in to check out!
Top guest reviews
Host:
the manager was great and so easy to work with, and didn't mind answering questions about bend from a locals point of view---very helpfuli have always had a fascination with tiny houses and jumped at the chance to try one outnice dining table that easily doubled for a desk/work space for me toowhen i walked in i noticed immediately how well maintained and clean she was, and then second how much bigger she appeared than what i was expectingproperty is nice and well maintainedLocation:
lovely park across the streeti enjoyed the relaxing couch in the living area for reading or watching tvRead more reviewsAmenities & Room:
the only downside is that it is not walkable to downtown but as such, provides a calm getaway from hustle and bustle of downtownvery comfy queen bed in the sleeping loft, with nice linensurprisingly private given that it is beside and behind main residencethere was a place for everything! well designed kitchen big enough to easily prepare food in, with all the appliances down to toastersmall but completely serviceable kitchen easy to cook full meals in
10. Luxurious stay for four
This 1924, former Emil Wienecke House has recently been renovated to cater to the need of modern travelers and yet it retains an old charm that you will fall in love with. Besides the spacious rooms to sleep in, the place also has a basement den that opens to the backyard for kids or for use as office space. Conveniently located from the river and the market, the place is a dream come true.
618 meters (0.4 ft) from Drake ParkTop guest reviews
Host:
bachelor ski resortthe owner mary was very helpful during the booking process and everything went smoothlyhistorical details throughout the house made it warm and invitingthis house was lovely - inside and outthe home was lovely and well maintainedLocation:
easy walking distance to downtownit was located in a very quiet neighborhoodlocation is prime for walking the waterfront, or returning from a floatreally enjoy the areaclose to everythingCleanliness:
the house was spacious, clean and with plenty amenitiestravelling with 3 grandkids (6, 7, and 9)Read more reviewsAmenities & Room:
the temp of the rooms can be a bit hard to manage because of single pane windows, but they kindly provide space heaters to helpthe kitchen was well stocked with dishes, cooking utensils, and pots and pansthe house is much more spacious that it looks in the photolots of room and stocked kitchen made cooking together fun and easythe bedrooms are spaced out where there is enough privacy for all
11. Beautiful property with vaulted ceilings
Looking for a place to crash in the center of the city, so you do not miss out on all the fun? This vaulted ceiling cottage is at a walking distance from the best pubs and eateries of Bend. And, yet is quiet and peaceful! Perfect for quick weekend getaways or family get-togethers with modern fixtures and fully functional kitchen (limited perishables) within the cottage, you are never far from anything! Perfect for small families, this property makes way for a memorable holiday in Oregon!
334 Northwest Hill Street
953 meters (0.6 ft) from Drake Park
12. Cozy house for three
This stand-alone cottage is an ideal abode for three for a weekend getaway. The old town charm is married with the modern amenities with tiled bath, TV, Wifi and tasteful fabrics and finishes. Location is such that one can simply walk down to some of the landmarks of Bend. The rooms are spacious and clean and you also get high-speed internet throughout your stay! You simply can’t find better than this!
55 NW Lake Place
958 meters (0.6 ft) from Drake Park
13. Comfy accommodation for a couple
On a tight budget? Worry not, for we have you covered. Apt for a weekend getaway, this quaint little cottage facilitates some me space away from the hustle and bustle of the city. With high vaulted ceilings, modern amenities and tasteful furnishing with easy accessibility to the Bend’s activities, this is just the place you must bunk at on your Bend vacation.
338 NW Hill Street
944 meters (0.6 ft) from Drake Park
14. Charming home with great views
A window to the “playground of the West”, Charming Bend home, is the destination for easy access to activities such as hiking and biking as well as to some wonderful places to dine and wine in. With bunker beds for the kids to sleep in and a view of the picturesque Pilot Butte, this cottage covers it all. At under USD 200, this cottage offers all the amenities of a 5-star hotel at a quarter of the price! What more can you ask for!
Bend, OR, US
3.09 km (2.0 mi) from Drake Park
15. A loft in historic Downtown
A naturally lit cottage in a quiet neighborhood of Old Bend, overlooking the Cascade Mountain, it offers a tranquil experience for a small family. Just walk down the quiet streets or chose to sit by the private deck and watch the sun setting over the hills, or relax in the authentic Scandinavian barrel Sauna with privacy. It is not always that you can get yourself an outdoor sauna at such affordable rates! This cozy property comfortably accommodates four and offers all the luxury amenities that most five star hotels offer! So, what are you waiting for? Make this amazing loft your vacation home the next time you plan a trip to Bend, Oregon!
648 meters (0.5 ft) from Drake ParkTop guest reviews
Host:
owner was very responsive to questionsin all, not a big deal unless maybe you have some 85+ days consecutivelythe owner, shawn, was easy to communicate with, friendly, and provided us with great recommendationsthe skylights provided great natural lighting and a cool breezeon warm summer days can get warm with no acLocation:
only a short walk to two parks and river walkreally enjoyed the loftwe really enjoyed out stayreally liked how close it was to restaurants and bars yet very quietwe enjoyed being able to walk shops & restaurantsCleanliness:
it was clean and comfortableplenty of linensbright and quiet apartmentgreat location, very comfortable and very cleanover all the place was clean and in great condition, but we found the bed and pillows pretty uncomfortableRead more reviewsAmenities & Room:
comfortable bed, all amenities of homedining table is a little smallvery comfortable and well-equippedbed in bedroom is quite firmincredibly comfy and spacious
16. Riverfront cozy accommodation
This century-old two-bedroom cabin overlooking the riverfront will certainly take you back to the life of Bend’s early residents, with some photographs on the wall to help your imaginations. This cozy property offers all the luxury amenities of a furnished home away from home. From clean and spacious rooms to air conditioning and even Wi-Fi, the property has it all! All you need to do is to just sit back and relax in the rusticity of the location or enjoy kayaking and canoeing at the low banks.
760 meters (0.5 ft) from Drake ParkAccommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 14 days before check-in.
Top guest reviews
Host:
great host!home is older and well maintained and furnishedvery relaxingswiffer sweeper would be nice to have to help with clean uphad a great dog friendly hike and lots of brewery stopsLocation:
great location, great riverfront rec areacute and charming housethe property is located just off of the river and walking distance to a number of different amenitieswaterfront amazingshort walk to the mill districtRead more reviewsAmenities & Room:
everything you might need in kitchen and bathroom are providedprobably time for a little freshening up, as the place itself is starting to look a little tiredwill definitely rebook time and time again!good parkinggreat location on the water- we enjoyed watching the crowds of floaters on a sunny day, and then the beautiful sunset that night
Enjoy a fun-filled vacation at Bend
Whether traveling for adventure, or for experiencing the old town charm or simply to relax, these accommodations will make your stay pleasant and enjoyable! Book your place today.
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