
Cottage holiday rentals in Deschutes County
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Top-rated cottage rentals in Deschutes County
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for cottage rentals in Deschutes County
Cottage rentals with a hot tub

Two Bedroom Charmer with Hot Tub
Great experience! The space was perfect for our needs. Walkable to good restaurants, cozy interior, and a fantastic deal.

TruNorthwest Retreat | Walk to Town • Pool • Dogs
Great location to explore Sisters and if you like to hike or bike your minutes to Peterson Trail and Whychus creek scenic overlook. The home was well stocked and very cozy, perfect for a family! Would definitely stay again!

The Blackberry Cottage
Tomi was great we mentioned our Keurig wasn’t working and he dropped off a new one great location and clean place

Cottage Live/Play in the Heart of Downtown Sisters
The cottage was very clean, excellent location, beautifully decorated. Would highly recommend.

Guest Favorite! Prime West Side Location, Hot Tub
Erin & her place are AWESOME! Would recommend 11/10.

Cloudchaser Cottage: Cozy Get-Away
Nice home in a great area of Sunriver, very close to Fort Rock park. Perfect for our family of four. We especially appreciated the family-friendly games, cozy hot tub, and wood fireplace. We had everything we needed!

Hot Tub, Fire Pit, Dog Friendly
Plenty of space for everyone to spread out and be comfortable, had everything we needed!

Come Stay and Play at Little Les Cheneaux Retreat
Our stay couldn’t have been better! The home was perfect and exactly what we needed for a fun family weekend getaway. Everything was extremely clean and just as described. The amenities at the resort were absolutely wonderful! Would have just loved better weather, but in Oregon it changes every five minutes and there’s nothing we can do about that! Can’t wait to come back again.
Pet-friendly cottage rentals

Blossom Cottage Studio
Very comfortable and quaint. I would highly recommend. Thank you!

Court St. Cottage | Downtown Prineville Getaway
It was a great place to stay! The house was well stocked with everything, and it was clean and comfortable!

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

Greeley Cottage: Steps to downtown Bend
What a great location just a block from downtown. We had a great stay and had everything we needed for the week!

Adorable + comfy! 24hr staff, HOT TUB, dogs
Private cottage rentals

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.

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.

Minutes walk Downtown/Cozy Cottage Retreat/Sauna
Debbie's cottage is so lovely! The home is really sweet — beautifully designed, great backyard, and a really central location. The home was clean and well-stocked and perfect for our family! Debbie was super responsive to all our questions and really kind and accommodating. I'd 100% recommend a stay here! We'll definitely book again if back in Sisters.

Guest Favorite! Prime West Side Location, Hot Tub
Erin & her place are AWESOME! Would recommend 11/10.

Contemporary Chic, Walk Downtown, Gourmet Kitchen
Absolutely loved our stay! The location was perfect—right in the middle of everything and so easy to get around. Jackson’s just a block away quickly became our favorite spot. Can’t wait to come back!

Adorable West Side Cottage, Pet Friendly!
We loved our stay and were so pleased to be able to bring our dog with. Perfect house, very light and nicely decorated. Stayed cool even when the outside temp was 96. Loved the yard, we could always find a shady spot to hang out and we enjoyed listening to the doves cooing. Quiet neighborhood within walking distance of parks, restaurants, and a grocery. We hope to come stay again!

The Tumalo House
We loved our stay in Tumalo. Perfect location for exploring Bend and enjoying meals in Bend, Sisters, and Redmond. The outdoor fire pit was a magical feature to enjoy the sunset on the first day of summer! The home was full of necessities and thoughtfully curated details . A lovely home to come home to after a day spent outdoors!
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