Cottage vacation rentals in Bend

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Popular amenities for Bend cottage rentals

Cottage rentals with a hot tub

Guest favourite
Cottage in Sisters
4.94 out of 5 average rating, 36 reviews

Steps to Downtown & Amazing Views-Hot Tub/Pool/AC

BrendaRating, 5 stars1 day ago
Very comfortable and well equipped home blocks from the two main streets of Sisters. The beds were very comfortable and everything was very clean. The kitchen was well equipped. The communication was responsive and friendly. There are no views from the home or front and back porches. The home is in a newer sub-development within easy walkable blocks of all of the downtown sites.
Cottage in Bend
4.89 out of 5 average rating, 307 reviews

The Blackberry Cottage

TylerRating, 5 stars6 months ago
We really enjoyed staying at Tomi’s place. Our dog loved the fully fenced in backyard! The home was very clean and the neighborhood was quiet.
Guest favourite
Cottage in Sisters
4.96 out of 5 average rating, 25 reviews

Cottage Live/Play in the Heart of Downtown Sisters

CarolineRating, 5 stars4 months ago
Fantastic cottage and location. We added nights onto our stay and did not want to leave. Highly recommend. David and Victoria gracious hosts and Jill the manager added the finishing touches to exceptional customer service.
Guest favourite
Cottage in Old Bend
4.96 out of 5 average rating, 251 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

DanRating, 5 stars1 month ago
Great place, close to downtown. Perfect for our family of four with two littles 8 & 11. Loved the alley parking as well. If Erin’s house was for sale, I’d be the new owner!
Guest favourite
Cottage in Bend
4.87 out of 5 average rating, 135 reviews

Guest Favorite! Prime West Side Location, Hot Tub

CohnerRating, 5 stars3 weeks ago
Erin is a great host and the place is close to everything. We really enjoyed our stay!
Top guest favourite
Cottage in Bend
5 out of 5 average rating, 37 reviews

Cloudchaser Cottage: Cozy Get-Away

ErinRating, 5 stars2 months ago
We had a wonderful stay at Williams place. It was everything we needed for the kids and ourselves!! The fun bedroom and play loft in the kids room, to the warm cozy living room , and finally the outside jacuzzi make it the perfect winter getaway for our yearly ski vacation. Thanks for a wonderful stay and we would and can’t to stay there again!!
Top guest favourite
Cottage in Sisters
5 out of 5 average rating, 8 reviews

Hot Tub, Fire Pit, Dog Friendly by @pinpointstays

KatherineRating, 5 stars2 weeks ago
The house was cozy and stocked full of anything you might need. Kenny was a very attentive host!
Superhost
Cottage in Redmond
4.86 out of 5 average rating, 59 reviews

Come Stay and Play at Little Les Cheneaux Retreat

ChereRating, 5 stars6 months ago
This home is perfect for a family with kids and a pet. Walking distance to the pool, very well equipped with everything you may need including a crock pot! Elizabeth and Daren were extremely fast responding, even with a last minute change request. We will definitely stay again. I recommend this home to anyone looking for a quiet getaway.

Pet-friendly cottage rentals

Top guest favourite
Cottage in Bend
4.98 out of 5 average rating, 103 reviews

The Tumalo House

AnneRating, 5 stars1 week ago
So great to have the Tumalo House available for Central Oregon visits. Its location makes it perfect for all there is to see and do! The house is perfectly appointed for everything you need!
Guest favourite
Cottage in Old Bend
4.91 out of 5 average rating, 126 reviews

2 Bedroom Delight In The Old Mill

LauraRating, 5 stars6 days ago
We love staying at The Sparrow cottage! This is the second year that my son and I have stayed here and we are already counting the days until we return! We came for Spring Break to visit our friends and get some snow/ski time. (we live in Hawaii :) The cottage is perfect for us! The location is great - you can walk to the Old Mill District, go ice skating at the pavilion, or grab your gear and head up to Mt Bachelor with ease. We love the quiet, peaceful neighborhood and the coziness of the cottage too. After a day of skiing or hiking in the crisp weather, it is nice to come home and snuggle by the fire and watch a movie. Ashley and Mona were amazing hosts - they brought us warm, fresh bread and offered great recommendations for restaurants and local spots. See you next March! Aloha!
Guest favourite
Cottage in Redmond
4.88 out of 5 average rating, 65 reviews

Blossom Cottage Studio

OpalRating, 5 stars3 weeks ago
Such a cute little cottage. A breath of fresh air being inside 🩵 Would definitely recommend and keep in mind for next trip!
Top guest favourite
Cottage in Bend
4.97 out of 5 average rating, 63 reviews

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

KathrynRating, 5 stars1 month ago
This was a lovely and peaceful stay. We loved hiking around the Badlands right out the back door with our dogs. The cabin was cozy and relaxing and had good amenities. You can tell Allison really put a lot of thoughtful touches into hosting and wants her guests to be comfortable.
Guest favourite
Cottage in Old Bend
5 out of 5 average rating, 6 reviews

Greeley Cottage: Steps to downtown Bend

NormaRating, 5 stars5 days ago
This place is right next to downtown. Very much enjoyed our stay with everything being so close. Definitely check out the Deschutes brewery down the street. Every one is so kind here definitely coming back in the summer.

Private cottage rentals

Top guest favourite
Cottage in Bend
4.95 out of 5 average rating, 415 reviews

Vintage Pink Hot Tub✓ Walkable✓

JeannetteRating, 5 stars2 days ago
Very sweet cottage, I enjoyed my stay! All the vintage charm made it feel like a real getaway. The kitchen was great for preparing meals, with everything I needed. Good bed and variety of pillows, which I appreciate. It felt like stepping into my great-grandmother's house!
Top guest favourite
Cottage in Sisters
4.98 out of 5 average rating, 155 reviews

Minutes walk Downtown/Cozy Cottage Retreat/Sauna

AllieRating, 5 stars1 week ago
A Perfect Stay in an Unbeatable Location! Our stay was absolutely fantastic! From the moment we arrived, we were blown away by the incredible location—everything we wanted to see and do was just steps away, making it the perfect home base for exploring the area. The host was incredibly communicative and responsive, ensuring that we had everything we needed for a seamless stay. Debbie’s thoughtful accommodations and quick replies made us feel truly taken care of. The home itself was spotless, beautifully decorated, and incredibly comfortable. One of the standout features was the well-stocked kitchen—everything we could possibly need was provided, from high-quality cookware to coffee and spices. It made cooking meals a breeze, which was such a nice touch! We couldn’t have asked for a better experience. If you’re looking for a place with a prime location, an attentive host, and all the comforts of home, look no further. We would absolutely stay here again in a heartbeat!
Guest favourite
Cottage in Old Bend
4.94 out of 5 average rating, 117 reviews

Two Bedroom Charmer with Hot Tub

TorkelRating, 5 stars1 month ago
We loved staying here! Clean, comfortable and cozy. Great aesthetic! Perfect for our ski week. Walkable yet calm. We hope to return!
Guest favourite
Cottage in Bend
4.93 out of 5 average rating, 275 reviews

NW Bend Hot Tub+Big Porch w/ Enclosed Yard+Pets OK

WintonRating, 5 stars3 weeks ago
Lisa’s place was cozy and comfortable. Perfect stay for my husband and I and our two dogs. Great location.
Top guest favourite
Cottage in Bend
4.97 out of 5 average rating, 118 reviews

Exceptional Downtown Cottage-Level II EV charger

ChristophRating, 5 stars5 months ago
Donald’s downtown cottage is a true gem, and he is the perfect host—warm, considerate, resourceful, and discreet. I almost hesitate to write the review he and the cottage deserve, fearing that it will become so popular I may never get the chance to return, as other lucky travelers discover this special place and keep coming back. Though far from my home in Europe, I felt immediately at ease in this cozy, beautifully equipped cottage nestled within a charming garden.
Guest favourite
Cottage in Old Bend
4.96 out of 5 average rating, 251 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

DanRating, 5 stars1 month ago
Great place, close to downtown. Perfect for our family of four with two littles 8 & 11. Loved the alley parking as well. If Erin’s house was for sale, I’d be the new owner!
Guest favourite
Cottage in Bend
4.87 out of 5 average rating, 135 reviews

Guest Favorite! Prime West Side Location, Hot Tub

CohnerRating, 5 stars3 weeks ago
Erin is a great host and the place is close to everything. We really enjoyed our stay!
Superhost
Cottage in Bend
4.79 out of 5 average rating, 137 reviews

New mid century cottage w/ hot tub & view

ColleenRating, 5 stars3 months ago
Cute little side house with a beautiful view of the mountains. The place was decorated super cute and has everything you need. It’s a dirt road with some good sized bumps so just be careful and go slow.

Quick stats about cottage rentals in Bend

  • Total rentals

    30 properties

  • Nightly prices starting at

    $101 CAD before taxes and fees

  • Total number of reviews

    4.6K 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