Guesthouse holiday rentals in Deschutes County

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.

The Guest Nest- quiet convenience in Midtown Bend!

Stay, relax, and rest in The Guest Nest! Delightful, comfortable, well-lighted, and close to everything! Your are at "nest level" in my upstairs apartment. My goal is to provide a welcoming comfortable place for you to stay! ! In return, I request that you treat my Guest Nest with care and respect-- just as you'd want guests in your home to do. You are not dealing with an impersonal corporate rental company. I clean and manage everything myself and do my best to make it perfect for you!

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.

BlueSpruce Guesthouse-Walkable RiverTrail/Downtown

The Blue Spruce is a charming, private second story guest house . It is accessed by exterior stairs, private entrance, and self check in. It is cozy, equipped with a full kitchen, sunny living room, 1 BD, and 1 Bath. Convenient location in a quiet neighborhood by downtown Bend, less than a mile to the river trail, coffee shops, brew pubs, and grocery. Great launching pad for mountain biking, hiking, skiing, golfing, fishing, whitewater and countless other adventures, you get the picture!

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.

Century Chalet - Tons of Light & Amazing Location!

We have a beautiful guest house with tons of natural light and all the amenities you'll need in the best location Bend has to offer. 1 Bedroom, 1 Bath, with a sunroom which can easily be used as a second bedroom whenever needed. The house has a full kitchen with stainless appliances. Best of all, you can't get any closer to Mt. Bachelor, the Deschutes, or Bend's trails. All while still being 8 minutes from downtown Bend.

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.

McKinley Place - A Retreat in SE Bend

The McKinley Place offers a fun and relaxing setting for singles, couples or small families. A great location for a complete Central Oregon trip. We are conveniently located to outdoor adventures, Bend's nightlife and tourist offerings as well as the business district. This is a beautiful ADU (Accessory Dwelling Unit) with private access. The unit faces an alley and has dedicated parking spots.