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.

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!

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.

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!

Bend Getaway | 2BR, King Bed, Garage, Fast WiFi

Renovated 2 level townhome, fully stocked, 100% cotton 400 thread count hotel quality sheets. Lives like a house and is the perfect home base for your outdoor adventures in Bend! The primary BR has a comfy King bed & private bathroom. The 2nd BR has a bunk bed (full on the bottom, and a single up top) with private bathroom. Main level features a spacious LR, DR & Kitchen along w/ a 1/2 bath. Located in the Boyd Acres neighborhood, just minutes to downtown and everything Bend has to offer.

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 Outside Inn - Private Studio Suite

Our cozy studio is placed in a peaceful cul-de-sac in NE Bend, just 10 minutes from the main destinations in town. Whether you’re traveling for business and need a naturally lit and inspiring workspace, or you’re coming to Bend to summit a peak, bike the trails, or hit all the hottest foodie spots, we've got you covered! The Outside Inn was designed to rejuvenate you so you’re able to experience and enjoy all that Bend has to offer. Breathe in the fresh mountain air and come stay awhile!

The Big Tiny

Reset and rejuvenate at the Big Tiny. Our thoughtfully designed, unique tiny house is fully equipped for your comfort and is surrounded with gorgeous desert views, and is also pet friendly. Conveniently located just 15 mins from downtown Bend. Enjoy all that Central Oregon has to offer. Start your days sipping coffee in the front yard while drinking in the fresh air. Relax after a day of adventure under the starry sky with a local beer or glass of wine next to the propane fire pit.

Rajneesh Aframe/Hot Tub, 10 min from downtown Bend

We are opening up our Aframe to host some visitors to Bend. This Aframe was originally built for the Rajneeshpuram, in Wasco county Oregon in the early 1980's. If you are not familiar with this interesting piece of Oregon history, we recommend you watch the documentary Wild Wild Country on Netflix. It is fascinating. Its a small little dwelling, we have a king sized Mattress in it (no bed frame due the space limitations), with easy access to a bathroom and shower in our home.

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.

Zen w/ Hot Tub, Office, Yard, Dog Friendly, Park

Welcome to your peaceful Bend basecamp, thoughtfully managed by The Home Co.—a local small business focused on clean, well-functioning homes with easy checkouts. This stylish 2-bedroom, 2-bath home is centrally located near Ponderosa Park and Pilot Butte, with easy access to Downtown, the Old Mill, and the Deschutes River. With a fully fenced yard, dedicated office, hot tub, and flexible living space, it’s perfect for families, remote workers, and pet lovers.

The Grove - King Beds & Hot Tub - No pets

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.