Guesthouse holiday rentals in Bend

A Couples Getaway in Old NW Bend

Old Bend meets new Bend in this spacious, newly constructed second level studio apartment in a century old neighborhood in NW Bend. The beautifully appointed room has private access and includes a well accessorized kitchen, comfortable furnishings, a queen size bed, and bathroom. As comfortable as we know you’ll be in the studio, you must get out and experience all Bend has to offer. Hiking, fishing, golf, lakes, rivers, Mt. Bachelor, beautiful sightseeing and many more activities are within a 30 minute drive. We think you’ll enjoy your stay without getting in your car at all. Within blocks you can visit local brew pubs and a great assortment of restaurants and shops. Beautiful downtown Bend is a 15 minute walk, or, a short bike ride on bikes we provide. Experience locally owned restaurants, bars, breweries, unique boutique shops, coffee roasters, bakeries, Drake park and more. This century old neighborhood which was home to many mill workers in the past has become a rejuvenated and vibrant area for a new generation. Many of the old houses continue to be remodeled and, at the same time, retain the old neighborhood feel.

Midtown gem I Cozy Fire I Full kitchen I Park View

Above garage one bedroom/one bath apartment in booming midtown. Open living with a gas fireplace, ac, full-sized kitchen, and gas stove. A large bathroom with a deep tub to relax or let the kids play. The bedroom features a cozy queen bed with a new Tempur-Pedic mattress topper and ample closet space. The east-facing deck is ready to sip your morning coffee while you wake up slowly, grill for an evening in or sit and work with the high-speed wireless as you watch the dog park across the street!

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.

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!

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

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.

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.

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.

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.

Cabin on quiet 3 acres 10 min to downtown Bend.

Enjoy the peaceful serenity of our guest house. Enjoy a large lawn, irrigation pond with deck for hanging out, and a firepit. Our home is 10 minutes drive to downtown Bend; 45 minutes to Mt Bachelor; 40 minutes to Smith Rock; 20 minutes to Phil's trailhead for mountain biking (All times are without rush hour traffic). Come enjoy all that Bend has to offer!