
Cottage vacation rentals in Painted Hills
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Top-rated cottage rentals in Painted Hills
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Painted Hills cottage rentals
Cottage rentals with a hot tub

Contemporary Chic, Walk Downtown, Gourmet Kitchen
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.

Guest Favorite! Prime West Side Location, Hot Tub
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.

Quaint Cottage Meets Modern Charm, Hot Tub, Fenced
Absolutely loved staying here. It is on a main road that’s fairly busy, but it’s extremely quiet which was surprising to me. The beds are probably the most comfortable ones I’ve ever experienced with an Airbnb. The host was very accommodating with early check in and we will definitely be back!

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

The Blackberry Cottage

Cottage Live/Play in the Heart of Downtown Sisters

Cloudchaser Cottage: Cozy Get-Away

Hot Tub, Fire Pit, Dog Friendly by @pinpointstays
Pet-friendly cottage rentals

2 Bedroom Delight In The Old Mill
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!

Blossom Cottage Studio

The Beautiful Sunset Cottage in Eastern Oregon!

Quiet central Oregon desert retreat with a view!

Blue Lagoon, Fish House Inn

Greeley Cottage: Steps to downtown Bend

One Block to Downtown, Hot Tub, Private Home, Yard

Court St. Cottage | Downtown Prineville Getaway
Private cottage rentals

Vintage Pink Hot Tub✓ Walkable✓
We had the great stay and instantly fell in love with this charming pink vintage getaway. Every detail felt so thoughtful — from the cozy decor to the super comfy bed. The place was sparkling clean, perfectly central, and had everything we needed, and the hot tub? Our dog felt right at home too. We’re already talking about our next visit — we’ll definitely be back! Thank you!

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

NW Bend Hot Tub+Big Porch w/ Enclosed Yard+Pets OK
This place was perfect for a quick business trip! The hot tub and view of the stars was wonderful in the evening. The fenced yard was perfect for our dogs tagging along. We so appreciated the extras such as the provided dog bed and towel. We also loved that the cleaning list was short and that the owners don’t let food go to waste. Overall, the home was quirky in a good way and worked great for our needs!

Exceptional Downtown Cottage-Level II EV charger
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.

Guest Favorite! Prime West Side Location, Hot Tub
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.

Quaint Cottage Meets Modern Charm, Hot Tub, Fenced
Absolutely loved staying here. It is on a main road that’s fairly busy, but it’s extremely quiet which was surprising to me. The beds are probably the most comfortable ones I’ve ever experienced with an Airbnb. The host was very accommodating with early check in and we will definitely be back!

Blue Spruce Cottage, 2/1, Modern, & Clean.
Chris was a responsive and kind host! Highly recommend

Cozy Home w/River Access, Hot Tub, 5min to Village
Courtney’s base camp was everything and more we had anticipated! My daughter and I spent a weekend at Courtney’s place. We absolutely loved the amenities in the backyard. Jacuzzi, comfy outdoor sofas and the fire pit for making s’mores. I was pleasantly surprised at how nice the inside was decorated. She had everything we could have asked for. Beds and linens were comfortable! Rent this place. You’ll love it!
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