Vacation rentals in Pilot Butte

Spacious Pet-Friendly Home • Fire Pit • Fenced Yd

Bring the whole family—including your dogs—and enjoy this spacious Bend retreat. Explore downtown, Mt. Bachelor, Deschutes River, hiking trails, and Bend's breweries, then come home to relax in your fenced backyard. Relax by the wood stove in the bright living room with mid-century décor. Grill on the patio, play croquet or cornhole, and gather around the fire pit. Fenced yard. Dogs welcome (up to 3). Park in garage. TVs in every bedroom, firewood provided, and self check-in with a smart lock.

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.

Private Indoor Pool + Hot Tub | Game Room

Alpenview Retreat | Perfect Gathering Home for Friends and Family Designed for unforgettable group stays, this spacious modern home combines luxury, entertainment, and location- just minutes from Downtown Bend and close to Mt. Bachelor. Spend your days skiing, hiking, or exploring, then come home to soak in the private, indoor heated pool and hot tub, sip your favorite beverage in the courtyard, or compete in your private game room. Perfect for families, friend groups, and multi-family trips.

Butler Corner - New, Clean & Minutes From Downtown

Relax and enjoy all that Central Oregon has to offer in this nice, clean and newer 2019 built home. Butler Corner is located in Midtown and sits on a corner lot in a nice quiet and charming neighborhood just minutes from Downtown. We invite you to stay a while in this comfortable space and think of it as your home away from home. ***Please keep an eye out for posted road signs, I recommend using Google or Apple Maps to help navigate the temporary one-way directions. Completion late Fall 2026

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.

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 . Garage is secure and available UPON REQUEST. Lastly, wireless internet is smokin, 1gb. Early check in available $10hr

Villa77: Renovated Stay Near Downtown & Old Mill

Newly renovated and thoughtfully designed, our airy apartment in Bend’s Midtown offers a 5-star experience. Enjoy crisp linens, plush towels, and fresh-ground local coffee brewed just the way you like it. Perfectly located near Downtown, the Old Mill District, and Bend’s best shops and eateries, our apartment is a cozy and stylish retreat. After a day of adventure, unwind in comfort at this charming home base! Owned by locals, this is the perfect launch pad for your Bend adventures!

Petite Suite: Midtown Warm & Welcoming This Winter

Welcome to our charming suite in the heart of midtown Bend, just 5 blocks from the beautiful Pilot Butte and only 5 minutes from downtown. Our studio apartment is the perfect choice for those looking for a comfortable and convenient home base for their Bend adventures. The location is ideal for exploring all that Bend has to offer. Take a hike on Pilot Butte, or stroll through the charming streets of downtown. You'll find plenty of shops, restaurants, and cafes nearby to enjoy.

The Church In Bend

The Alliance Tabernacle Church, built in 1923, is reported to be the first house of worship west of the Mississippi to be built entirely by volunteers from the congregation. By the 1970s the building had fallen into disrepair. Beginning in October 2014 the current owners began the process of restoring the building to it's original condition under the supervision of the Historic Landmark Commission. This special place is close to everything, making it easy to plan your visit.

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.

MCM Home in Bend

Welcome to our home in Bend, OR! Our cozy, newly renovated midcentury modern home is centrally located in charming Midtown Bend. Enjoy a bonfire in the backyard, or relax after a day on the mountain in the elevated living area. Take a stroll with your pup down to Hollinshead Park to enjoy the trees and beauty of the neighborhoods. We are conveniently located: 5 Minutes to Downtown Bend 7 Minutes to Old Mill District 35 Minutes to Mt. Bachelor