Guesthouse holiday rentals in Deschutes River

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 2027 for fire 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.

Location · Family · Backyard

Renovated Condo - Ideal Location

This is Central Oregon's premier location for recreation activities. Your stay at this sleek condo will have you encircled by peaks, lakes, meadows, culture, adventure, breweries, festivals, family fun and more. Offering a cozy condo that comfortably sleeps 2 guests with a queen size bed, a mini kitchen, the convenience of on-site laundry facilities. Plus, a living/dining are comforts that would be hard to find in an average hotel. Come make this your launching pad as you experience Bend!

Value · Location · Condition

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Welcome to our Clackamas Riverfront Guest House—a peaceful riverside retreat blending rustic charm and modern comfort. Relax in your private hot tub and sauna, unwind by the fireplace, and enjoy stunning river views. Fish, kayak, or raft right from the backyard. Bedrooms include white noise machines and earplugs to help with normal traffic during commute hours on our scenic road. The guesthouse is attached but its own private unit with its own separate entrance and parking. Enjoy your stay!!

Family · Value · Check-in

Near River Trail - Pet-Free - King - Local Hosts

We take pride in maintaining high standards in this spacious studio—our first Airbnb and still one of our most popular. Guests love the proximity to the Deschutes River Trail, just a 10-minute walk to downtown, and First Street Rapids Park two houses away. Then come home and stretch out on the ultra-comfy king bed (it has been called The Ruiner Of Morning Ambition) Trust the reviews—they say it best! We maintain a low-allergen environment using unscented products and do not ever allow pets.

Value · Family · Solo travel

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.

Value · Family · Wi-Fi

Lakeside Cabin with Loft and Outdoor Pavilion

Secluded light-filled cabin with a modern farmhouse vibe overlooking a private lake. Located 1 mile from Mt. Hood National Forest, with plenty of hiking, paddling, fishing, and biking opportunities! Onsite amenities include canoes, open air pavilion with large stone fireplace, walking trails and plenty of lawn games. Cabin sleeps four, with main level queen bed and loft queen with ladder access. Living room provides home theater experience. Kitchenette and outdoor gas BBQ.

Family · Value · Sleep quality

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.

Value · Location · Skiing

Adorable 1-bedroom 1930s farmhouse.

WELCOME TO BEND. This 1930s Farm house sits on 17 acres and has been updated to be a cozy 600 ft sq 1 bedroom getaway. It is located just East of Bend directly across the street from the Bend Municipal Airport and is easy access for anyone flying into town for the night. It is far enough out of town to enjoy the starry sky, but also close enough (10 minutes) to still enjoy the comforts of town (restaurants, Costco, Grocery Stores, Coffee shops, food trucks, etc.).

Location · Family · Outdoor spaces

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.

Location · Family · Comfort

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.

Family · Value · Long stay

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.

Value · Family · Pets

Muse Cabin in old growth forest w/cedar hot tub

Enjoy our beautiful cozy cabin that is heated exclusively by a wood stove, on the edge of a magical old growth cedar forest on our 11 acre farm and vineyard. Relax on the deck built into the trees, and sleep peacefully in the loft bed, as you soak in the nature around you. The cute out house is just down the path and the cedar hot tub/ outdoor shower is next to the garden.

Location · Family · Breakfast