Cottage vacation rentals in Painted Hills

Find and book unique cottages on Airbnb

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Popular amenities for Painted Hills cottage rentals

Cottage rentals with a hot tub

Guest favorite
Cottage in Bend
4.96 out of 5 average rating, 255 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

SarahRating, 5 stars2 weeks ago
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
An outdoor patio area is surrounded by a wooden fence, featuring a round black table with four chairs, a vibrant red umbrella, and a coffee table. Colorful flowers and greenery are planted along the edges, creating a serene outdoor space.
Cottage in Bend
4.87 out of 5 average rating, 137 reviews

Guest Favorite! Prime West Side Location, Hot Tub

KatieRating, 5 stars1 month ago
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.
Guest favorite
Cottage in Bend
4.9 out of 5 average rating, 134 reviews

Quaint Cottage Meets Modern Charm, Hot Tub, Fenced

CarlieRating, 5 stars2 weeks ago
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!
Guest favorite
A charming cottage exterior is presented, featuring a welcoming front porch with red chairs and decorative throw pillows. Flower beds, filled with white and purple blooms, line the path leading to the entrance. Three vertically positioned windows above the door allow natural light to enhance the facade.
Cottage in Sisters
4.95 out of 5 average rating, 38 reviews

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

The exterior of the cottage is shown with a charming deck and two white chairs positioned under string lights. A well-maintained path leads through lush greenery and stone steps to the entrance, highlighting the inviting atmosphere of the cottage.
Cottage in Bend
4.89 out of 5 average rating, 307 reviews

The Blackberry Cottage

Guest favorite
A charming cottage is depicted with a sloped roof and inviting front porch. Adjoining chairs sit on a lush green lawn, surrounded by well-maintained shrubs and seasonal flowers. A stone pathway leads to the entrance, framing the structure in a serene outdoor setting.
Cottage in Sisters
4.96 out of 5 average rating, 25 reviews

Cottage Live/Play in the Heart of Downtown Sisters

Top guest favorite
Cottage in Bend
5 out of 5 average rating, 38 reviews

Cloudchaser Cottage: Cozy Get-Away

Top guest favorite
An outdoor seating area is surrounded by snow-covered ground, featuring a rectangular fire pit at the center. Several chairs with cushions in various colors are arranged around it. The cottage's warm lights glow invitingly through large glass doors, framed by tall trees in the background.
Cottage in Sisters
5 out of 5 average rating, 10 reviews

Hot Tub, Fire Pit, Dog Friendly by @pinpointstays

Pet-friendly cottage rentals

Guest favorite
A charming cottage is set amidst lush greenery, featuring a light-colored exterior with decorative window accents. A welcoming porch leads to the front door framed by a gabled roof, while a wooden fence encloses the yard, enhancing privacy and inviting a sense of warmth.
Cottage in Bend
4.91 out of 5 average rating, 126 reviews

2 Bedroom Delight In The Old Mill

LauraRating, 5 stars1 month ago
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!
Guest favorite
A cozy seating area is presented with a gray armchair beside a small white dining table. A decorative mirror and greenery adorn the wall, while sunlight filters through a nearby window, illuminating the space. A rug adds warmth to the wooden floor.
Cottage in Redmond
4.88 out of 5 average rating, 65 reviews

Blossom Cottage Studio

Cottage in Mitchell
4.77 out of 5 average rating, 64 reviews

The Beautiful Sunset Cottage in Eastern Oregon!

Guest favorite
A spacious deck is framed by a wooden pergola, featuring two individual chairs positioned for relaxation. Wide windows of the cottage allow natural light to fill the space, while the surrounding landscape reveals expansive views of native plants and shrubs, enhancing the overall tranquility.
Cottage in Terrebonne
4.9 out of 5 average rating, 296 reviews

Quiet central Oregon desert retreat with a view!

Superhost
A quaint cottage, surrounded by lush greenery, features a welcoming entrance with a small porch. Several outdoor seating options are available, including a table and chairs. A grill is positioned on the side, inviting outdoor dining. The setting offers a peaceful atmosphere.
Private room in Dayville
4.9 out of 5 average rating, 163 reviews

Blue Lagoon, Fish House Inn

Guest favorite
The exterior of the Greeley Cottage features a charming white facade with dark trim. Multiple windows offer natural light, while potted plants flank the entrance. A black front door is adorned with a decorative lamp, inviting guests into the home.
Cottage in Bend
5 out of 5 average rating, 9 reviews

Greeley Cottage: Steps to downtown Bend

Guest favorite
Cottage in Bend
4.94 out of 5 average rating, 157 reviews

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

Top guest favorite
A comfortable living area features warm brown leather sofas adorned with decorative pillows. A small ottoman is centered in the seating arrangement. Natural light filters through sheer curtains, and a flat-screen TV is mounted on the wall, enhancing the inviting atmosphere.
Cottage in Prineville
4.95 out of 5 average rating, 57 reviews

Court St. Cottage | Downtown Prineville Getaway

Private cottage rentals

Top guest favorite
Cottage in Bend
4.95 out of 5 average rating, 418 reviews

Vintage Pink Hot Tub✓ Walkable✓

MarinaRating, 5 stars5 days ago
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!
Guest favorite
The living area features a cozy sofa and a wooden coffee table atop a woven rug. Large windows invite natural light, while a television is positioned on a wooden stand. A dining area can be seen in the background, enhancing the open layout.
Cottage in Bend
4.94 out of 5 average rating, 117 reviews

Two Bedroom Charmer with Hot Tub

TorkelRating, 5 stars2 months ago
We loved staying here! Clean, comfortable and cozy. Great aesthetic! Perfect for our ski week. Walkable yet calm. We hope to return!
Guest favorite
A wooden deck is surrounded by lush greenery and tall trees, featuring a patio set with a large umbrella. A cozy seating area is arranged with striped chairs and a table, creating an inviting outdoor space for relaxation.
Cottage in Bend
4.93 out of 5 average rating, 282 reviews

NW Bend Hot Tub+Big Porch w/ Enclosed Yard+Pets OK

ColleenRating, 5 stars3 weeks ago
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!
Top guest favorite
Cottage in Bend
4.97 out of 5 average rating, 119 reviews

Exceptional Downtown Cottage-Level II EV charger

ParkerRating, 5 stars3 weeks ago
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
The image captures a scenic view of the Deschutes River, featuring calm blue waters with gentle ripples. Green grassy banks line the river, while a few kayakers enjoy the water. The background includes trees and a glimpse of nearby buildings, offering a sense of tranquility.
Cottage in Bend
4.87 out of 5 average rating, 137 reviews

Guest Favorite! Prime West Side Location, Hot Tub

KatieRating, 5 stars1 month ago
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.
Guest favorite
The exterior of the cottage is highlighted, showcasing a welcoming front door painted in a vibrant coral hue. Two bright pink chairs are positioned on the porch, with a landscaped pathway leading through a manicured yard bordered by wooden fencing and tall pine trees.
Cottage in Bend
4.9 out of 5 average rating, 134 reviews

Quaint Cottage Meets Modern Charm, Hot Tub, Fenced

CarlieRating, 5 stars2 weeks ago
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!
Top guest favorite
A modern living area features a light-colored hardwood floor, complemented by a sectional sofa adorned with blue cushions. A wooden coffee table sits center stage, while a dining table for four and a stainless-steel kitchen appliances complete the welcoming space. Natural light floods through multiple windows.
Cottage in Bend
4.99 out of 5 average rating, 119 reviews

Blue Spruce Cottage, 2/1, Modern, & Clean.

NormRating, 5 stars1 week ago
Chris was a responsive and kind host! Highly recommend
Top guest favorite
Cottage in Sunriver
4.97 out of 5 average rating, 117 reviews

Cozy Home w/River Access, Hot Tub, 5min to Village

KarlaRating, 5 stars2 weeks ago
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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