Cottage holiday rentals in Sisters

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Popular amenities for Sisters cottage rentals

Cottage rentals with a hot tub

Top Guest favourite
Cottage in Bend
4.94 out of 5 average rating, 79 reviews

Cozy 3 bedroom house, hot tub, near Sun River

JasonRating, 5 stars10 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!
Guest favourite
Cottage in Sisters
4.95 out of 5 average rating, 41 reviews

TruNorthwest Retreat | Walk to Town • Pool • Dogs

AnnieRating, 5 stars1 week ago
Great location and space in sisters! As described!
Cottage in Orchard District
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 favourite
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.
Guest favourite
Cottage in Bend
4.87 out of 5 average rating, 142 reviews

Guest Favorite! Prime West Side Location, Hot Tub

EmilyRating, 5 stars3 weeks ago
Erin’s place was wonderful and centrally located. We enjoyed our stay and everything was as described in the posting. We would stay again!
Top Guest favourite
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.
Superhost
Cottage in Redmond
4.87 out of 5 average rating, 62 reviews

Come Stay and Play at Little Les Cheneaux Retreat

KristinRating, 5 stars2 weeks ago
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!
Top Guest favourite
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!

Pet-friendly cottage rentals

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

2 Bedroom Delight In The Old Mill

AshleyRating, 5 stars3 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 favourite
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
Guest favourite
Cottage in Bend
4.92 out of 5 average rating, 163 reviews

Amazing Location! | Charming, Cozy Cottage

JohnRating, 5 stars10 months ago
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!
Guest favourite
Cottage in Terrebonne
4.89 out of 5 average rating, 300 reviews

Quiet central Oregon desert retreat with a view!

CharlesRating, 5 stars1 week ago
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.
Guest favourite
Cottage in Bend
5 out of 5 average rating, 11 reviews

Greeley Cottage: Steps to downtown Bend

JamesRating, 5 stars1 month 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.
Cottage in Crescent
4.79 out of 5 average rating, 24 reviews

Deschutes 2 Bedroom Cabin

MeganRating, 5 stars3 months ago
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!
Top Guest favourite
Cottage in Prineville
4.95 out of 5 average rating, 62 reviews

Court St. Cottage | Downtown Prineville Getaway

ErinRating, 5 stars2 weeks ago
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.
Cottage in Crescent
4.72 out of 5 average rating, 32 reviews

Cascade Studio Cabin

MaudeRating, 5 stars4 months ago
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

Superhost
Cottage in Bend
4.9 out of 5 average rating, 458 reviews

Downtown, Modern Nostalgia--walk to shops, cafes

MeganRating, 5 stars2 weeks ago
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!
Top Guest favourite
Cottage in Bend
4.94 out of 5 average rating, 418 reviews

An Urban Base to Bend's Adventures!

KaitlinRating, 5 stars2 months ago
This place was amazing. It had everything I needed, was centrally located and incredibly clean
Top Guest favourite
Cottage in Old Bend
4.99 out of 5 average rating, 115 reviews

Riverfront Cottage– Walkable Old Bend Stay

PaulaRating, 5 stars1 day ago
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!
Guest favourite
Cottage in Bend
4.97 out of 5 average rating, 117 reviews

River Camp House

GailRating, 5 stars3 days ago
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.
Top Guest favourite
Cottage in Bend
4.95 out of 5 average rating, 420 reviews

Vintage Pink Hot Tub✓ Walkable✓

DebiRating, 5 stars1 month ago
Quaint and quiet. Clean and great location. Met our expectations. Super friendly hosts and very responsive. Have already recommended to friends.
Top Guest favourite
Cottage in Sisters
4.98 out of 5 average rating, 165 reviews

Minutes walk Downtown/Cozy Cottage Retreat/Sauna

SandyRating, 5 stars1 week ago
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.
Guest favourite
Cottage in Old Bend
4.96 out of 5 average rating, 262 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

MichelleRating, 5 stars2 weeks ago
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.
Top Guest favourite
Cottage in Bend
4.98 out of 5 average rating, 112 reviews

The Tumalo House

Npulone@Gmail.ComRating, 5 stars2 weeks ago
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.

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