Cottage vacation rentals in Bend

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Popular amenities for Bend cottage rentals

Cottage rentals with a hot tub

Superhost
Cottage in Old Bend
5 out of 5 average rating, 7 reviews

Perfect spot for groups & families

KimberleRating, 5 stars1 week ago
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!
Top guest favorite
Cottage in Bend
4.94 out of 5 average rating, 79 reviews

Cozy 3 bedroom house, hot tub, near Sun River

JasonRating, 5 stars9 months ago
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!
Cottage in Bend
4.89 out of 5 average rating, 308 reviews

The Blackberry Cottage

MollyRating, 5 stars3 weeks ago
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
Cottage in Bend
4.87 out of 5 average rating, 141 reviews

Guest Favorite! Prime West Side Location, Hot Tub

SarahRating, 5 stars4 weeks ago
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!
Guest favorite
Cottage in Old Bend
4.96 out of 5 average rating, 260 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

JudyRating, 5 stars2 weeks ago
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!
Top guest favorite
Cottage in Bend
5 out of 5 average rating, 38 reviews

Cloudchaser Cottage: Cozy Get-Away

Sarah Rating, 5 stars2 months ago
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.
Top guest favorite
Cottage in Bend
5 out of 5 average rating, 38 reviews

Bright/Quiet/Cozy w/ hot tub & huge fenced yard

GrantRating, 5 stars9 months ago
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!
Top guest favorite
Cottage in Old Bend
4.98 out of 5 average rating, 52 reviews

Historic Old Town Bend Cottage

NicholasRating, 5 stars1 week ago
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

Guest favorite
Cottage in Sisters
4.95 out of 5 average rating, 41 reviews

TruNorthwest Retreat | Walk to Town • Pool • Dogs

AnnieRating, 5 stars6 days ago
Great location and space in sisters! As described!
Guest favorite
Cottage in Sisters
4.96 out of 5 average rating, 27 reviews

Cottage Live/Play in the Heart of Downtown Sisters

KrystynaRating, 5 stars1 month ago
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.
Top guest favorite
Cottage in Sisters
5 out of 5 average rating, 16 reviews

Hot Tub, Fire Pit, Dog Friendly

AshleyRating, 5 stars1 week ago
We had a great stay! House was very clean and Kenny was a great host
Superhost
Cottage in Redmond
4.87 out of 5 average rating, 61 reviews

Come Stay and Play at Little Les Cheneaux Retreat

MarkRating, 5 stars4 weeks ago
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.
Cottage in Bend

Cute cottage! Hot Tub + near mountain and trails

Cottage in Bend

Popular cottage at Tetherow! Hot Tub + comfy beds

Cottage in Bend

Popular 2-bedrm at Tetherow, comfy+clean

Cottage in Bend

Comfy mountain cottage at Resort, HOT TUB, dogs ok

Pet-friendly cottage rentals

Guest favorite
Cottage in Old Bend
4.92 out of 5 average rating, 130 reviews

2 Bedroom Delight In The Old Mill

AshleyRating, 5 stars2 weeks ago
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!
Guest favorite
Cottage in Redmond
4.89 out of 5 average rating, 72 reviews

Blossom Cottage Studio

LorettaRating, 5 stars3 weeks ago
Great place to stay for a quick overnight trip
Top guest favorite
Cottage in Bend
4.97 out of 5 average rating, 65 reviews

Dog-Friendly Ranch Cottage w/ Yard ~ 13 Mi to Bend

JoshuaRating, 5 stars2 months ago
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!
Guest favorite
Cottage in Old Bend
5 out of 5 average rating, 11 reviews

Greeley Cottage: Steps to downtown Bend

JamesRating, 5 stars3 weeks ago
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

    G$14,687 GYD 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Deschutes County
  5. Bend
  6. Cottage rentals