
Cottage vacation rentals in Bend
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Top-rated cottage rentals in Bend
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Bend cottage rentals
Cottage rentals with a hot tub

Perfect spot for groups & families
AMAZING! There are so many positives to this property! This was our first time visiting Oregon and it exceeded our expectations. The AIRBNB was so special and unique. The property is quite large and provides plenty of privacy, room for yard games and intimate camp fires. The (3) cottages are absolutely adorable and beautifully and uniquely appointed. We had everything we could need and the bedding was super cozy! This property is walking distance to the river for amazing morning coffee walks, afternoon bike rides and of course, adventure. We loved having a rental car to explore hiking trails and also enjoyed a half day river rafting trip. There are plenty of restaurants, tasting rooms, breweries and shopping within walking distance. Ashley was fabulous to communicate with and provided very clear instruction and guidance. We highly recommend this property for your group! Thank you Ashley and thank you OREGON!

Cozy 3 bedroom house, hot tub, near Sun River
We had a fantastic stay at Talia's place near Sunriver! The home was cozy and clean and had everything we needed for a relaxing getaway. The location was perfect—close to all the outdoor activities we love, yet tucked away in a quiet, peaceful setting. Talia was a fantastic host, quick to respond, and very accommodating. We couldn't have asked for a better experience and look forward to returning soon!

The Blackberry Cottage
We stayed for the Pole Pedal Paddle and had a great time here! Really enjoyed the hot tub and being so close to Pilot Butte. Tomi was helpful and responsive when we had a question about the WiFi. We would love to come back!

Guest Favorite! Prime West Side Location, Hot Tub
Erin’s place was perfectly located and super cozy. We didn’t spend as much time there as I hope we can in the future but it was exactly what we needed and we appreciated that. Erin is very easy to communicate with and she navigates problem solving with ease . We hope to stay again and enjoy the amenities!

Contemporary Chic, Walk Downtown, Gourmet Kitchen
I have rented many Vacation rentals in the USA and Mexico . I would rate this as the best yet! You can walk everywhere, we walked to the concert to the river and out to eat. The restaurant recommendations were all outstanding. Erin was very responsive and friendly. The cottage was beyond well stocked with everything. We did plan to bring our dogs but they ended up staying home but the yard would be perfect for them. Last but not least all the neighbors were so friendly!

Cloudchaser Cottage: Cozy Get-Away
We loved this property. It was in a great area and we loved the neighborhood. The house was well equipped and very peaceful and great floor plan. The just was so helpful and responsive. Would recommend and will rent again.

Bright/Quiet/Cozy w/ hot tub & huge fenced yard
Really enjoyed Dan's place. We have two dogs and they loved the large backyard, especially sniffing for the mule deer that liked to visit the apple tree in the front yard. The outdoor patio with hot tub and pergola was wonderful, inspiring some ideas for our own home when we return. Dan was very accessible and responsive, helping in any way and communicating when he was in the area. The location is great as well - very close to Tumalo and right near the Tumalo Creek Park, and a short drive from everything else in Bend. We'll be keeping this place mind and may have to visit again in the future!

Historic Old Town Bend Cottage
We loved our stay and felt right at home the moment we walked in. Everything was so clean and comfortable and thought-through and easy and well-communicated. The location was super convenient. Check-in/out was easy as could be. Everything was spotlessly clean and there were so many nice homey touches. The backyard spa, the huge rain shower head, the wonderfully comfortable bed—it all made our trip to Bend feel like the perfect blend of vacation and at-home comfort and allowed us to enjoy our trip to the fullest!
Cottage rentals with a pool

TruNorthwest Retreat | Walk to Town • Pool • Dogs
Great location and space in sisters! As described!

Cottage Live/Play in the Heart of Downtown Sisters
We had a wonderful stay in Sisters at David & Victoria’s place. Walkable to town, peaceful neighborhood, perfect view of the Sisters mountain range. Their place had plenty of space for us and the bed was comfortable.

Hot Tub, Fire Pit, Dog Friendly
We had a great stay! House was very clean and Kenny was a great host

Come Stay and Play at Little Les Cheneaux Retreat
We had a great stay here, for more than a week. The house was clean and comfortable and had great amenities. It was a 5 minute walk to the pickleball courts, where we played pickup games with neighborhood regulars for several days. The neighborhood was quiet, yet friendly. The house was very close to BLM land and trails. Beautiful sunsets just minutes away, with a view of at least 5 mountains. This part of Eagle Crest connects quickly with Eagle Crest Boulevard, where you can get to either Redmond or Sisters in about 10 minutes. Great stay.

Cute cottage! Hot Tub + near mountain and trails

Popular cottage at Tetherow! Hot Tub + comfy beds

Popular 2-bedrm at Tetherow, comfy+clean

Comfy mountain cottage at Resort, HOT TUB, dogs ok
Pet-friendly cottage rentals

2 Bedroom Delight In The Old Mill
Amazing place to stay in Bend. Walked or took the cruiser bikes everywhere. Headed to a concert at the ampitheatre, toodled along the river, and explored downtown -- all just 8-10 minutes away. Had a great stay!

Blossom Cottage Studio
Great place to stay for a quick overnight trip

Dog-Friendly Ranch Cottage w/ Yard ~ 13 Mi to Bend
Such a whimsical and unique place, and such a beautiful location nestled up against the Badlands. Had a wonderful long weekend looking at the stars and hiking in the sagebrush and juniper. Clearly this place was a labor of love, so many thoughtful touches from the art to the books to the dog supplies. Close enough to Bend to get out to eat but also remote enough to feel like you are in the outback. Thank you!

Greeley Cottage: Steps to downtown Bend
We had a great stay. The place is spacious - separate living room, kitchen with dining area, two bedrooms, separate bathroom. It's great that way. And all clean and tastefully appointed. The location is a mix of slightly funky (it's basically located on an alley) and wonderful - you are a block or two from downtown Bend. It's a great combo, actually. We really enjoyed it.
Quick stats about cottage rentals in Bend
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
4.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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