Chalet vacation rentals in Southern Oregon

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Popular amenities for Southern Oregon chalet rentals

Family-friendly chalet rentals

Guest favorite
An expansive view of a golf course is highlighted, featuring rolling green hills and sand traps. Majestic mountains rise in the background against a clear blue sky. A serene water feature is visible, surrounded by lush trees, emphasizing the natural beauty of the landscape.
Chalet in Redmond
4.88 out of 5 average rating, 24 reviews

Eagle Crest Resort Condo with Mountain Views!

LionneRating, 5 stars8 months ago
We had a great stay in the house of Sue! We especially loved the view from the deck on the river. Although the house is on a resort, it is really quiet, because it is on the edge of the resort. But it is still easy to enjoy the pools and sport facilities on the park, with even one pool within a short walking distance. The house itself is really comfortable and all the amenities are there. Sue is a great host, she was very responsive.
Guest favorite
The chalet features a rustic exterior with a gabled roof and large triangular windows that allow natural light to fill the living space. A spacious deck is equipped with seating and an umbrella, surrounded by landscaped greenery, creating an inviting outdoor area.
Chalet in Redmond
5 out of 5 average rating, 12 reviews

the McIntosh Chalet

ChristinaRating, 5 stars1 month ago
Every year for my husband’s birthday, we rent this type of cabin at Eagle Crest. This one was very clean and comfortable. The carpet seemed new and the beds were very nice. We enjoyed hiking Smith Rock, Cline Butte and Steelhead Falls and then coming back to a super clean hot tub. The stargazing was phenomenal. I agree with other guests that having to check in at the lodge where they couldn’t find my name was less convenient than having a key code on the door, but it ended up ok since I had the confirmation email. If you plan on cooking at all, I’d advise future guests to bring any pantry supplies like oil (only salt and pepper were provided) and any foil, baggies, etc. I only mention this because I never know if I need to bring these things. Otherwise, the house has everything we needed to enjoy three nights in this beautiful area. I’d stay here again.
Guest favorite
Chalet in La Pine
4.95 out of 5 average rating, 118 reviews

Elk View Lodge - Private Luxury Family Retreat

AlyshaRating, 5 stars15 months ago
Elk View Lodge did not disappoint. It comfortably fit our group of 4 adults and 8 children. We had loads of beautiful snow outside and a cozy and pristine home inside for our long weekend away! Michelle was incredibly responsive and helpful. We will definitely be coming back— hopefully next time for a summertime trip to explore all the hiking, biking and rafting in the area.
Top guest favorite
The exterior of a two-story home is presented, featuring large windows that provide ample natural light. A wraparound deck extends around the house, with a shaded area beneath. A fire pit encircled by seating is visible, set against a backdrop of rolling hills and greenery.
Chalet in Prineville
4.92 out of 5 average rating, 95 reviews

Juniper Ridge Retreat

NatashaRating, 5 stars8 months ago
We had a great stay. The house was extremely clean and well stocked with plenty of towels, blankets, coffee/teas and other thoughtful touches.

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