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 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, 112 reviews

Truly One of the Very Best Riverfront Homes!!!

GilRating, 5 stars5 days ago
My wife and I stayed here with our dog and 1 month old newborn. Great location, very walkable, we didn’t need to use the car once. And the host is so nice and makes the stay feel like home. Highly recommend.
Top guest favorite
Cottage in Bend
4.95 out of 5 average rating, 419 reviews

Vintage Pink Hot Tub✓ Walkable✓

MatthewRating, 5 stars1 week ago
We loved our stay here! It was our first time staying in Bend. Jay and Dina were communicative and the cottage was on point. The amenities and hot tub were very nice. It’s a great short walk to town or the river trail. Thanks for having us!
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 stars2 weeks 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, 284 reviews

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

LaurenRating, 5 stars2 weeks ago
We loved this place so much!! The sweet vintage kitchen as the center piece to the home really felt cozy and worked great for our family. All the rooms and bedding was decorated beautifully. My daughter loved the bunk beds in her room and our bedroom was so serene and comfortable. The hot tub on the back porch was amazing! We started almost every day off with a soak. Our doggies loved the fenced in yard and deck for taking naps. The neighborhood is so killer! Walkable to so many cool places in Bend! This is definitely gonna be our go to Airbnb when we visit! Thanks for everything! :-)
Guest favorite
A welcoming front porch features two white folding chairs and a small table. Potted flowers add color to the space. The green door complements the light exterior, while overhead lights enhance visibility. Natural light filters through the surrounding trees.
Cottage in Bend
4.94 out of 5 average rating, 345 reviews

Adorable West Side Cottage, Pet Friendly!

HeatherRating, 5 stars3 days ago
This was such an awesome find on short notice. Such a cozy cottage with so much character. Anna set up a travel crib for us since we were getting in late which was super helpful. The sheets on our bed were so soft that we had to figure out what they were so we can buy them—Kirkland Signature. Haha! We will definitely stay again if it’s available!

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 stars2 weeks 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
The exterior of the chalet is showcased, featuring a peaked roof and large windows that reflect the sunset. A spacious deck with railing is visible at the front, surrounded by a well-manicured lawn and tall trees, providing a calming natural setting.
Home in Redmond
4.83 out of 5 average rating, 29 reviews

Dog Ok! Full Resort Access. Garage - Cozy Chalet

LyssyRating, 5 stars1 month 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 stars1 month 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, 113 reviews

Beautiful Sisters Condo - Great location

DerekRating, 5 stars2 weeks 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!
Guest favorite
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 stars2 months 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:)
Guest favorite
A serene lake scene is depicted with calm water reflecting the blue sky. Sandy shores are visible, with several boats and paddleboards seen at the water's edge. Lush trees line the background, providing a natural setting, while a few people enjoy recreational activities near the water.
Home in Tygh Valley
5 out of 5 average rating, 20 reviews

Eagle Point at the Lake!

DaveRating, 5 stars2 months ago
Bridget and Joshua were excellent hosts - super fast response to any questions we had and always helpful. The house was warm, spacious and perfect for 3 of us up here for an early season fly fishing trip. Kitchen is well stocked, lots of sofa/armchair space for relaxing in the evening and other amenities like washer/dryer made it a great choice for us. We’d stay here again for sure!
Guest favorite
A spacious open-plan living area features wooden walls and large windows, allowing natural light to flood in. A modern kitchen with an island bar connects to a dining space with a large table surrounded by wooden chairs. Comfortable seating is arranged nearby.
Home in Black Butte Ranch
4.89 out of 5 average rating, 152 reviews

Family retreat on Black Butte Ranch

DianeRating, 5 stars8 months ago
Sue was a wonderful host. Quick to respond to my questions. And her instructions and local tips were very helpful. Such a peaceful home and a good size for our family to have space and be comfortable. Great big kitchen with everything needed for cooking. Thank you!

Destinations to explore

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