Top Private Holiday Homes in Deschutes County in 2026

A snowy landscape with two prominent snow-capped mountains and a forest in the foreground.

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Our top choices for Deschutes County holiday homes

A resort with multiple swimming pools, a water slide, and a large building with a modern design.

1. Eaglewood Condo 8

Sunriver

"Beautiful home! Very large and comfortable. The kitchen was very well appointed, beds were comfortable, and the hot tub was lovely. The bikes they provide are a very nice touch. It’s right across from the pool, so that was a little annoying when we tried to take an afternoon nap one day, and we couldn’t really sleep very late because the kids started playing loudly as soon as it opened. Minor inconveniences, though. Overall, the home is a great space."

Katharine

A fire pit with two Adirondack chairs, a pond, and a lodge in the background.

2. Klamath by Avantstay Premier Lakeside Cabin w/ Spa, Fire Pit & Lake Views

Sunriver

3. Towhee Lane 5

Sunriver

A spacious kitchen with wooden cabinets, a large island, and a dining area with a chandelier.

4. 20 Red Cedar 3 Bedroom Home

Bend

A wooden deck with outdoor furniture, a large vase, and a patio umbrella.

5. Big Bear Home features Private Entrance and Patio with Fire Pit by RedAwning

Bend

A cozy cabin interior with a wooden interior, a dining area, a fireplace, and a large window overlooking a yard.

6. Deer Park Cabin 3 Bedroom Home by RedAwning

Redmond

7. Wildflower Condo 54

Sunriver

Pat

8. Coyote Lane 9

Sunriver

Michelle

A two-story house with large windows, a balcony, and a deck area.

9. Amazing Riverfront on the Water- Big Sky Bend

Deschutes River Woods

An outdoor seating area with wooden tables and chairs, a covered patio, and a building with a clock and American flag.

10. 10min to Downtown Bend Chic 2bdr

Orchard District

Stephanie

11. Aquila Lodge 5

Sunriver

A spacious living room with a fireplace, a blue recliner, a gray sofa, and a wooden coffee table.

12. Hot-tub, Pet-friendly, 30 min to Mt Bachelor!

Southeast Bend

"The home was in a lovely location near local attractions. Lots of seating, comfortable beds, large deck. The hot tub worked great. Communication with the management company was poor, quoted three different pet fees different from the listing. The owner honored what was in the listing. The mgmt provided different door codes and different check in/out instructions from the app or the info onsite. "

kristin