
Cottage holiday rentals in Sisters
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Top-rated cottage rentals in Sisters
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Popular amenities for Sisters cottage rentals
Cottage rentals with a hot tub

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!

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

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!

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.

Guest Favorite! Prime West Side Location, Hot Tub
Erin’s place was wonderful and centrally located. We enjoyed our stay and everything was as described in the posting. We would stay again!

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.

Come Stay and Play at Little Les Cheneaux Retreat
We had a wonderful time! The home was comfy and had everything we needed while also clean and welcoming. We were in the area for our son’s baseball tournament, and this was a perfect home base for games in Sisters and Redmond. We enjoyed the hot tub and grill on the back patio, rec center, and walking our dog on the trails. We’ll definitely consider staying here again next time we’re in the area. Thank you!

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!
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

Amazing Location! | Charming, Cozy Cottage
Great little house with a lovely backyard and walkable to tons of good spots in Bend. Hope we can come back in the winter and stay again!

Quiet central Oregon desert retreat with a view!
We stayed the last days in May and the first days in June 2025. The place was clean with everything needed to relax, enjoy our stay and also do our own cooking. We sat outside at sunset and watched the stars come out. We hiked at Smith Rock State Park and visited Bend and Redmond. It was a great stay and I'm recommended it to friends and hope to be back next year.

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.

Deschutes 2 Bedroom Cabin
Stunning lake view from beautiful picture window. Watched a brilliant sunrise, ducks and an eagle from the window. The kids found a sweet little sledding hill that was the perfect size for them, made snowmen and had snowball fights. Beds were comfortable and cabin was warm. Kitchen was missing lids for the pots and basic staples. The general store was open. Would definitely visit again!

Court St. Cottage | Downtown Prineville Getaway
Great place to stay! The location was peefect, within walking distance to downtown, food trucks and parks. The house was amazing, it was cozy and had everything we needed. Super clean, and the host was super responsive.

Cascade Studio Cabin
We had a lovely time. We went in the winter and cabin was well heated, and the morning by the lake were just magic.
Private cottage rentals

Downtown, Modern Nostalgia--walk to shops, cafes
Loved this lil house! Close to everything! The hooks in the rooms are perfect! It is a very well thought out living space. They have everything you need and it’s adorable!

An Urban Base to Bend's Adventures!
This place was amazing. It had everything I needed, was centrally located and incredibly clean

Riverfront Cottage– Walkable Old Bend Stay
The cottage is wonderful, right on the river, incredibly clean and well stocked. There’s a great assortment of water toys too, paddle boards, kayaks, and inflatables. Even better is that Jackie is an amazing host, so welcoming, friendly, and helpful. Fantastic location too!

River Camp House
Beautiful furnishings. Well stocked. Clean and uncluttered. Minimal check out responsibilities. Daniel was quick to respond to a question. We will stay here again next year.

Vintage Pink Hot Tub✓ Walkable✓
Quaint and quiet. Clean and great location. Met our expectations. Super friendly hosts and very responsive. Have already recommended to friends.

Minutes walk Downtown/Cozy Cottage Retreat/Sauna
Awesome location and easy house to stay in. Stocked kitchen with everything you'd forgotten made it a super easy vacation to handle. Our second time here and we'll be back again.

Contemporary Chic, Walk Downtown, Gourmet Kitchen
We’ve stayed in Bend before and chose this unit due to the location and the proximity to downtown and The Old Mill district. We were able to walk to many locations in both areas including breweries, restaurants, parks, shops and trails. The unit itself was very clean and nicely decorated. The neighbors were quiet and the beds were comfortable. There was pretty much everything you would need. We’ll definitely stay here again.

The Tumalo House
Adorable and spotless clean home right near the new and fun shopping and eating options in Tumalo. Central to Sisters and Bend or Redmond sights but so quiet and fun walkable community away from the traffic. For me it was also close to Bend Equine for my horses special treatment. I loved working here, walking to delicious coffee and even a little local coffee. I didn't eat at the Bite this time but it is right across the street and has great choices I have enjoyed before. Highly recommend and would stay here again.
Destinations to explore
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