Holiday rentals in Pilot Butte

Modern retreat in central Bend

Enjoy our new custom-built ADU located a block away from the Deschutes River in a quiet residential neighborhood, just a 10-minute walk from downtown along the River Trail. In this modern, bright, and private space, you'll enjoy the luxuries of hardwood floors, waterfall countertops, a built-in workspace, heated tile bathroom floors, a 55" Smart TV, BBQ and fire pit, and endless hot water—plus off-street parking and EV charger. One king bed, one daybed with a trundle, and one queen sleeper sofa.

Midtown Gem With Cozy Fire and Park Views

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!

River Run Bend Bungalow & Romantic Spa Grotto

Relaxing, private spa & sauna grotto is ready for your romantic Bend getaway! This quiet, wooded, centrally located standalone bungalow is steps from the Deschutes River trail and within easy walking distance of Mill Dist. and Hayden Amphitheater. It boasts a comfy king bed w/premium down bedding & pillows, dedicated free parking (+ extra cars or small RVs), outdoor dining and patio area, washer/dryer, and a kitchen fully stocked with everything you need for fun and relaxation for all seasons!

The Blackberry Cottage

This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.

Quiet Escape: Fireplace, 5min to Downtown & River

Relax on the private balconies overlooking the park. After your coffee take a 2 minute walk down to the Deschutes river trail. Or walk 10 minutes and you're in downtown Bend. After a day of outdoor and ski adventures, you'll love the king size bed or relaxing by the fireplace. You'll have super fast wifi with Netflix, and a Smart TV in each room. Looking to stay longer? Send us a message to talk about long term stays and remote working. Locally owned and operated. Book your stay today!

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!

Quail Park Haven in NW! King Beds & Hot Tub

Relax in this peaceful NW Bend home with king beds and access to Quail Park. Enjoy natural light from the skylights and high ceilings. Kick back in the expansive backyard with mature plantings, tall trees and flagstone paths. Multiple patios including a deck off the living room, a paver patio with fire-pit, hot tub, outdoor furniture and gas BBQ. EV charger, HEPA air filter and garage access. No parties or pets please. Trip insurance recommended if illness, weather or smoke may be an issue.

Blue Spruce Cottage, 2/1, Modern, & Clean.

This cottage is located in the heart of Midtown - 20 mIn walk downtown & walking minutes from great food/beer/coffee. You will enjoy a very quiet, newer home, with air conditioning & 2 KING tempurpedic beds, tucked under mature Spruce trees. For active guests a hose is available to wash bikes, washer/drier and indoor racks to dry your clothing. A full kitchen and BBQ for meal prep. Garage is secure and available UPON REQUEST. Lastly, wireless internet is super fast, 300mbs.

Larkspur Garden Guesthouse

Located in Bend's Midtown and with access to the Larkspur trail that leads to iconic Pilot Butte, this bright, newly built 450 sq. foot apartment balances cozy and modern elements to make your stay in Bend comfortable. Equipped with a full kitchen, a separate room with a queen bed, a deep, relaxing tub, a sofa that converts into a memory foam queen bed, a TV with access to Netflix, and a separate laundry room. Our space is a great option for 2 guests, but it can fit up to 4.

The Grove at Midtown Manor - King Beds & Hot Tub!

Adorned with murals of forests, our Airbnb invites you to immerse yourself in nature's embrace. Relax on the sunken patio surrounded by live plants, or unwind in the private hot tub under the stars. Inside, enjoy cozy amenities including a fully-equipped kitchenette and luxury linens. Our hideaway promises an enchanting experience you won't forget. Book now and let the magic unfold! Please read the entire listing for details on potential for noise.

Central Modern Guesthouse with EV Charger

We built this home out of a passion for creating welcoming spaces. Years ago, we renovated a motel on the coast - an experience that sparked our love of hospitality and shapes how we host today. We live around the corner with our kids, a golden retriever, and a few cats. Mike’s a local realtor, and Betsy manages business ops for the local fire department. We love books, music, and helping you discover the best of Bend - trails, eats, and community.

Orchard District Studio

A cozy studio apartment; this converted garage space has tall ceilings making it feel light and airy. Located in Bend's Orchard District, it is walking distance to Hollinshead Park & Pilot Butte. We are NOT within walking distance to downtown, however it is only a 5 minute drive to downtown & 15 minutes to outdoor recreation opportunities. Hosts live in the main house. LGBQT+ BIPOC friendly.