Vacation rentals near Painted Hills

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Popular amenities for Painted Hills vacation rentals

Cottages near Painted Hills

Superhost
The entrance of a century-old mill home is depicted, featuring a light-colored front door beneath a covered porch. Two comfortable outdoor chairs are positioned on either side of the porch, with a well-maintained garden and a wooden fence visible in the background.
Cottage in Bend
4.9 out of 5 average rating, 456 reviews

Downtown, Modern Nostalgia--walk to shops, cafes

DhirajRating, 5 stars1 month ago
The house was clean and in a good location in walking distance to downtown Bend in a quiet neighborhood. The beds and pillows were comfortable. Having 2 bathrooms was a plus for our group of 4. There are good restaurants in walking distance (15-20 min walk ) or 5 minutes by car. Highly recommended.
Top guest favorite
A patio area is shown, featuring four black chairs arranged around a small table. A grill is positioned nearby, and colorful autumn foliage surrounds the outdoor space. A stone pathway leads through the garden, enhancing the natural setting.
Cottage in Bend
4.97 out of 5 average rating, 112 reviews

River Camp House

DanRating, 5 stars1 month ago
Everything was great. The location is perfect for access to Bend, Mt Bachelor, and other outdoor activities. The house was exactly as described. Highly recommend.
Top guest favorite
A tranquil outdoor fire pit area features five bright red Adirondack chairs arranged in a semicircle around a stone-lined fire pit. The yard overlooks a peaceful river, surrounded by grasses and trees, creating an inviting space for relaxation.
Cottage in Bend
4.99 out of 5 average rating, 110 reviews

Truly One of the Very Best Riverfront Homes!!!

JuliaRating, 5 stars2 weeks ago
My friend our dogs had the most wondering stay here this spring! The location is ideal, I was able to walk to everywhere in downtown/Old Mill with the dog with such ease. The neighborhood is peaceful, but do know that there is a public walkway across the river extending to a bridge across the river so you can be seen in the yard. Jacalyn was so welcoming, the house was cozy, and the fire pit set up was perfect. The kitchen was one of the best stocked at any airbnb I've been too. Everything has been thought through with great detail
Top guest favorite
Cottage in Bend
4.95 out of 5 average rating, 418 reviews

Vintage Pink Hot Tub✓ Walkable✓

MarinaRating, 5 stars4 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 interior space features warm wooden flooring and white walls. A black wood-burning stove is positioned against one wall. A small round dining table with wooden chairs can be seen, alongside a doorway leading to a bathroom and a kitchen area. A spiral staircase adds an element of charm.
Cottage in Bend
4.92 out of 5 average rating, 163 reviews

Amazing Location! | Charming, Cozy Cottage

JohnRating, 5 stars8 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!
Top guest favorite
A wooden sauna, designed in an oval shape, is positioned in a private outdoor area. Two slatted lounge chairs with blue and white striped cushions are placed nearby, set against a backdrop of green grass and trees, creating a peaceful retreat.
Cottage in Sisters
4.98 out of 5 average rating, 158 reviews

Minutes walk Downtown/Cozy Cottage Retreat/Sauna

KatieRating, 5 stars1 week ago
Absolutely recommend staying at Debbie's place! The house was even better in person than in the pictures/description! Debbie's home was inviting and everything we needed for our girls weekend! Debbie was an excellent host and very responsive! It was super walkable to downtown and just what our group needed!
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 stars2 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!

Other great vacation rentals in Painted Hills

Top guest favorite
Home in Sisters
5 out of 5 average rating, 75 reviews

Stunning Mountain View Home~Unsurpassed views

HannahRating, 5 stars1 week ago
Brenda’s Mountain View home was absolutely wonderful. Brenda was responsive, friendly, and flexible. The home was gorgeous and peaceful and was fully furnished with many amenities. Would 100% recommend and would love to stay again if I ever needed! Thank you Brenda!
Superhost
Home in Redmond
4.83 out of 5 average rating, 29 reviews

Dog Ok! Full Resort Access. Garage - Cozy Chalet

LyssyRating, 5 stars3 weeks ago
We had a lot of fun staying here! We enjoyed the selection of board games. The back patio was lovely, I just wish the weather would have cooperated, it would have been great to hang out there more. Everything was nice and as expected.
Top guest favorite
A classic two-story house is set against a vibrant sunset sky. The wrap-around porch features soft lighting, while neatly landscaped gardens with tall grass enhance the welcoming ambiance. Concrete pathways lead up to the entrance, complemented by lush greenery lining the yard.
Home in Sisters
4.99 out of 5 average rating, 72 reviews

Downtown Pine Mountain Paradise

ChristiRating, 5 stars3 weeks ago
My family had a great time for spring break. The house was beautiful and fit our needs well. We hiked, hot tubbed, golfed, shopped, and had great food. The host was very responsive and helpful. We will definitely be back!
Top guest favorite
A spacious living area is displayed with a large sectional sofa arranged around a soft area rug. Natural light brightens the space through the window, while a modern dining area is visible in the background, featuring a long table. Wood flooring adds warmth to the room.
Condo in Sisters
4.99 out of 5 average rating, 112 reviews

Beautiful Sisters Condo - Great location

DerekRating, 5 stars1 week ago
Debbie’s condo was perfect for a quick getaway in Sisters. The unit was clean, easy to access, and had everything we needed. It was an easy walk to 3 Creeks Brewery!
Superhost
Home in Bend
4.8 out of 5 average rating, 5 reviews

Stellar Cabins

JessicaRating, 5 stars2 months ago
Beautiful and comfortable homes! We so enjoyed our stay at the Stellar Cabins. They were clean and picture perfect. Babette was very responsive and accommodating. Highly recommend!
Top guest favorite
Townhouse in Redmond
5 out of 5 average rating, 19 reviews

The Great Escape at Eagle Crest

TimRating, 5 stars1 month ago
The name says it all. This place truly is the great escape. It was wonderful to get away from the grind of work to come to a place like this. The place was very clean extremely comfortable and even though it’s situated in a 4 unit complex you feel like you’re all alone. It backs up to blm/farm land so nobody is wandering around behind the place while you’re enjoying the sun on the back patio. The hot tub and deep soaker tub were nice after our hikes during the day. If you’re looking for a great escape from everyday life then this is the place. I will definitely be booking again in the future. Thank you for a great weekend:)
Top guest favorite
Home in Bend
4.94 out of 5 average rating, 140 reviews

Bend Or Private Getaway one acre

DebraRating, 5 stars6 days ago
Erik was very responsive both during the process of securing the reservation and after. The house was extremely well furnished with supplies, paper products, towels, etc. and I would have to say it was the best we had ever seen in our travels. From Kcups to kitchen staples, to desk supplies…this house had it all! We had a geriatric sibling reunion this time but we also have grandkids that would have so enjoyed the game room. So much fun and a very enjoyable stay!
Guest favorite
Townhouse in Redmond
4.95 out of 5 average rating, 75 reviews

Updated EagleCrest Townhouse w/ resort amenities.

BethanyRating, 5 stars6 months ago
Lindsey's place worked perfectly for a quick weekend trip for my mom and I, visiting my brother in Bend. It was a peaceful haven and had all of the accomodations we required. We liked that there were restaurant options at the resort for when we needed something quick or didn't want to travel too far. Our only regret is that our stay was so short that we didn't get to take full advantage of the grounds or Lindsey's local recommendations. There are lovely walking and biking paths throughout and we would have loved to have had the opportunity to enjoy them more. Thank you for everything, Lindsey!

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Wheeler County
  5. Painted Hills