Guesthouse holiday rentals in Deschutes County

Quail View-Pets Welcome, Great Outdoor Space

Quiet tree lined cul-de-sac location this executive master suite has all the comforts of home. Kitchen has dishwasher, gas range & large refrigerator. Private patio surrounded by gardens & paver walkways, access to shared deck with gas grill. Big screen TV for relaxing & desk for working. Expansive bathroom with dual sinks, walkin shower, heated towel rack & heated tile floor. Extra Large Closet includes washer/dryer & also has heated tile floors. Private entrance & separate off street parking.

Ranch Cottage: Desert, Forest, Horses, Hot Tub

Beautiful guest cottage studio, with mountain views, in the southeast Bend neighborhood of Sundance. 15 minutes to town and 45 minutes to Mt. Bachelor ski area. This special ranch property is two blocks away from endless recreation in the Deschutes National Forest. (PLEASE NOTE; national forest access has been closed as of May 1, 2025-May 2026 for fuel reduction and restoration. blm trails are open) Includes one king Sleep Number bed and one queen Murphy bed. Private hot tub out the back door.

Sound Smith Guesthouse 2\2 - Park Setting

Enjoy SE Bend In this gorgeous brand new space. Beautiful fully furnished 2 bed, 2 bath guest home located adjacent to Larkspur park and Juniper Swim and Fitness where there is a playground as well as trails that go all the way to Pilot Butte. Property has gate access to the park. The lower level of the building is our family business, a guitar/ukulele warehouse with a small office/showroom. Feel free to schedule an appointment to order or check out some of our instruments. SoundSmithGear.com

NEW Tranquil Retreat On Canal

Charming, clean, comfortable, fully renovated guest house on 3 acres, nestled by a canal. A quiet escape near Pine Nursery Park, just 5 miles from downtown and less than 20 minutes from the airport. Enjoy beautiful natural light, vaulted ceilings, large bathtub, and balcony with outdoor seating and a beautiful view. Fully stocked kitchen, washer & dryer, heat & AC, blackout shades, board games, books, amenities for kids, smart TV, and a Blu-ray player for rentals from The Last Blockbuster.

Bend Ranch Guesthouse on 20 acres

Enjoy our private/detached guesthouse and wake up surrounded by nature on a 20 acre property bordered by farms and views of the Sisters Mountains. Excellent WIFI. Featuring wedding venue, Sage & Honey Spa, tube/lifejacket rentals. On the 2nd floor, 1 king bed, 1 queen bed, queen sofa bed, Full kitchen, refrigerator, dishwasher, microwave, hot plate, toaster oven, Keuirg. 17min to downtown Bend, 12min to downtown Redmond/Airport, 35min to Mt. Bachelor, 30mins to Sisters, 10mins to Tumalo.

Modern lofted guest house

Enjoy our recently completed lofted guest house. Just 3.7 miles from smith rocks and walking distance to Terrebonne restaurants, coffee and local grocery store. Centrally located, 15 min to the airport and just a 30 min drive to Bend. Our guest house has a fully stocked kitchenette ( NO OVEN) with a toaster oven/air fryer, and an induction cook top. Sit back and relax outside in the Adirondack chairs while drinking a Nespresso coffee. Wifi is provided as well as a Roku T.V and DVD.

The Outpost Bend

The Outpost is a seperate guest home located on our 10 acre hobby farm. It offers spectacular views of the Cascades, stunning sunsets and a peaceful, private location 15 minutes east of downtown Bend. The property adjoins public land, and is on a quiet country road. Our family lives onsite with our 3 sons, dogs, hens, and sheep. The Outpost has a private driveway, use of basketball court, and a lovely private outdoor seating area. 45 min drive to Mt. Bachelor.

Suburban Forest guest house with garage

Experience Bend to the fullest! Adventure is just outside your door with only a few traffic circles between you and the mountains. All of the best eats, drinks, and shopping are within a few miles, and you can store all of your gear in your private garage while you spend time in town. Our home is not suitable for pets or emotional support animals. ESA animals are not considered service animals by AirBnb or the State of Oregon. Please respect this rule.

Modern Downtown Cottage near Outdoor Adventure

Nestled in the heart of Downtown Redmond, this beautifully designed cottage offers the perfect blend of convenience and comfort. You'll find yourself within walking distance of charming coffee shops and restaurants, and just 14 minutes away from the breathtaking Smith Rock. The Redmond Airport is less than 10 minutes away, and if you're planning a visit to Bend, you can be downtown or floating on the Deschutes River in under 20 minutes.

Charming studio in the heart of town

The Arrow cottage is located in the heart of Bend between the historic downtown and desirable Old Mill district. It is truly the perfect location, just steps from the Columbia river park, walking distance from the amphitheater, 10 Barrel Brewery, Good Life Brewery, Jackson's Corner and Active Culture to name a few. Our complimentary bikes make make it easy for you to zip downtown for your morning coffee or evening happy hour.

Central Oregon Hot Spot!

Come relax and stay a while! Located near beautiful La Pine State Park, it’s a short drive to all the beautiful lakes/rivers, fishing, boating, and hiking. Not to mention restaurants, breweries, and tap houses. There is a large propane grill available and outdoor lounge area with a propane fire pit to be enjoyed year-round. There’s even a dry sauna! We’ve updated our Wi-Fi so you can easily connect and enjoy.

Botanical Studio in the Trees - Steps to Trails

Wake up to treetop views at this spacious bungalow peppered with live plants, unique art, and a stunning cedar ceiling. Stroll down to the Deschutes River Trail, which can take you downtown. Enjoy the locals-favorite First Street Rapids Park, then curl up and restore on the ultra comfy king bed. Creature comforts abound! No pets please. Trip insurance recommended if illness, weather or smoke may be an issue.