Cottage holiday rentals in Bend

If you’re seeking a place close to downtown Sisters this is the perfect place to stay. While it might not have the wooded charm of Black Butte, we loved the setting for its walking distance to Sisters Coffee Co. and other shops. The house is so thoughtfully supplied with everything you might want for cooking in the kitchen or relaxing on the comfortable furniture. We really appreciated the fluffy towels and bedding.

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.

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.

The house is so comfortable and conveniently located in Old Bend. You can walk 7-15 minutes in any direction of the house and get to a variety of shops, restaurants, bars, coffee shops and river trails. We didn't drive our car for 3 days and were able to walk to lots of fun stuff. The house is quiet, immaculate and well cared for. The clean hot tub is in the privately-fenced side yard. We would definitely stay here again.

This was one of the most convenient places I’ve stayed in Bend. Super walkable with lots of food options close by. It was also great to walk our daughter to the playground at Harmon park, then to Drake park to enjoy the river. The fenced yard in the back was great for our dogs. There’s also a grassy fenced yard in the front too but one of my dogs could jump over it. The Airbnb had all necessary amenities and we had a wonderful time! Would definitely recommend.

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.

What a wonderful experience. The neighborhood, the house, the yard, and every little detail was thought of. No wonder why you are a super host Kenny. We loved our experience and can’t wait to come back.

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.

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!

Such a cute little cottage. A breath of fresh air being inside 🩵 Would definitely recommend and keep in mind for next trip!

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!

We absolutely loved our stay at the Greeley Cottage! The space was perfect for my partner, myself and our dog! It was a very short walk to a lot of great local restaurants, bars and shopping. And a short drive to a lot of other great spots within town. When we checked in, there were some issues with the batteries in the keypad lock, but the host was very quick to respond and assist with getting us checked in! Everything we needed for our short stay was in the unit, which made for a very comfortable getaway. We would definitely love to come back sometime soon!

We loved our stay here! It was our first time staying in Bend. Jay and Dina were communicative and the cottage was on point. The amenities and hot tub were very nice. It’s a great short walk to town or the river trail. Thanks for having us!

Absolutely recommend staying at Debbie's place! The house was even better in person than in the pictures/description! Debbie's home was inviting and everything we needed for our girls weekend! Debbie was an excellent host and very responsive! It was super walkable to downtown and just what our group needed!

We loved staying here! Clean, comfortable and cozy. Great aesthetic! Perfect for our ski week. Walkable yet calm. We hope to return!

We loved this place so much!! The sweet vintage kitchen as the center piece to the home really felt cozy and worked great for our family. All the rooms and bedding was decorated beautifully. My daughter loved the bunk beds in her room and our bedroom was so serene and comfortable. The hot tub on the back porch was amazing! We started almost every day off with a soak. Our doggies loved the fenced in yard and deck for taking naps. The neighborhood is so killer! Walkable to so many cool places in Bend! This is definitely gonna be our go to Airbnb when we visit! Thanks for everything! :-)

Don’s cottage in Bend had it all. The location was perfect—just a short distance from downtown, but it felt like a peaceful retreat. The location is private and serene with a fair amount of wildlife — squirrels digging for nuts, birds chirping and even white-tailed deer munching on the lawn right in the backyard. The trail behind the cottage that winds along the Deschutes River was a gorgeous bonus. The cottage itself felt like home—cozy, welcoming, and stocked with everything one could possibly need. Don was a fantastic host, and would happily stay here again.

The house is so comfortable and conveniently located in Old Bend. You can walk 7-15 minutes in any direction of the house and get to a variety of shops, restaurants, bars, coffee shops and river trails. We didn't drive our car for 3 days and were able to walk to lots of fun stuff. The house is quiet, immaculate and well cared for. The clean hot tub is in the privately-fenced side yard. We would definitely stay here again.

This was one of the most convenient places I’ve stayed in Bend. Super walkable with lots of food options close by. It was also great to walk our daughter to the playground at Harmon park, then to Drake park to enjoy the river. The fenced yard in the back was great for our dogs. There’s also a grassy fenced yard in the front too but one of my dogs could jump over it. The Airbnb had all necessary amenities and we had a wonderful time! Would definitely recommend.

This was such an awesome find on short notice. Such a cozy cottage with so much character. Anna set up a travel crib for us since we were getting in late which was super helpful. The sheets on our bed were so soft that we had to figure out what they were so we can buy them—Kirkland Signature. Haha! We will definitely stay again if it’s available!