Vacation 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!

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!

Lodge Vibes in the City with Gym & Sauna

Instantly transition into vacation-mode. A modernized 3,200+ square foot log home located within the city of Bend. Enjoy the natural wood surroundings and massive vaulted ceilings that allow for space to spread out and relax. Get your chef on in the fully equipped kitchen or opt for the outdoor BBQ and pizza oven. No parties, pets or ESA's please. Trip insurance recommended if illness, weather or smoke may be an issue. *Note major construction behind the home! Townhome Development in Progress.

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.

Spacious Stay | 2 Living Rooms + Patio | Sleeps 12

Welcome to your spacious yet cozy home away from home in Bend! Designed with groups in mind, this light-filled retreat features two inviting living rooms and an open-concept layout that makes gathering easy and comfortable. Located just 2 miles from downtown Bend, enjoy quick access to the top shops, breweries, and restaurants. Even closer, you’ll find a selection of local dining and drink spots within walking distance on the east side — plus Pilot Butte State Park just a short stroll away.

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!

*Private Entrance & Deck* 10 min to Downtown Bend!

This tranquil room is sealed off from the main house and comes with a private deck entrance and all the amenities you need to enjoy Bend. 10 min drive/20 min bike ride to downtown. The room boasts an ensuite bath with 2 separate sinks and shower. Large walk-in closet as well. Large screen Smart TV on swivel mount comes with Netflix. Small dining area includes mini fridge, Nespresso machine, toaster, and microwave. Quiet neighborhood close to local dog parks and Pilot Butte state park.

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.

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.

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.

Drake @ The DUPE - blocks from Old Mill District -

Drake: Located blocks from the Old Mill District, this beautifully updated 2-bed, 2-bath townhouse blends privacy with an unbeatable location. Walk or bike to the Old Mill, Deschutes River, dining, and the Hayden Homes Amphitheater. Tucked in a serene, tree-lined setting, the private home features a bright kitchen with updated appliances, a primary suite with a walk-in tile shower, and a separate porch with a BBQ grill. The perfect mix of modern comfort and convenience.