Guesthouse holiday rentals in Bend

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!

Family · Location · Wi-Fi

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

Location · Family · Cleanliness

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 · EV charging

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.

Value · Location · Laundry

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 · Location · Long stay

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. I clean and manage everything myself and do my best to make it perfect for you! (Please note there is an extra charge for a 3rd person)

Location · Family · Kitchen

Private Studio w/ Hot Tub near the Deschutes River

The Fresca Studio has a kitchenette, hot tub, BBQ & bikes. Downtown Bend is a few miles away, McKay cottage, Deschutes River Trail & Sawyer park are a short walk, and all things Bend eat, drink, biking, hiking, skiing are all close by. The studio is separate from the main house w/ a private entry & patio, fully furnished, and easy access to/from the highway and parkway. Not suitable for children under 5y/o, 2 guests only and children are considered guests. No pets. See you soon!

Location · Value · Barbecue

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.

Family · Location · Quiet

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.).

Family · Location · Backyard

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 · Bathroom

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.

Family · Value · Air conditioning

The Sunshine Loft

Be one of the first to experience this unique guest house! We just finished building the Sunshine House. Enjoy snow capped mountain views from your cozy private space. Indoor/outdoor living with a comfy outdoor sofa and a patio heater for chilly nights. Watch a spectacular sunset and then enjoy a movie in bed while watching the stars. We have friendly dogs available for petting! There are stairs to get to the unit.

Location · Family · Outdoor spaces