House holiday rentals in Prineville Reservoir

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.

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.

Cozy Three Story Lookout Tower

Thank you for your interest in The Cozy Lookout Tower! Our unique vacation home is really a destination location rather than just a place to stay while you explore the area. Many of our guests are repeat guests that use our home as a place to recharge, relax, cook, read, talk, play games and connect with that special someone. There are some lovely hikes in the area, we encourage you to bring your dog and enjoy the beautiful surroundings by taking some hikes then returning for a soak in the tub!

Cozy Downtown Redmond Cottage

Welcome to our cozy Redmond cottage, located in the heart of downtown! Enjoy walking to local breweries, restaurants, and shops, all just steps away. This inviting space offers a perfect blend of comfort and convenience, ideal for couples or solo travelers. Unwind in the cozy living area after a day exploring Central Oregon. Experience the best of Redmond right outside your door! Conveniently close to: 15 minutes to Smith Rock 25 minutes to Bend 8 minutes to Deschutes County Fair & Expo Center

Smith Rock Gardens

You'll enjoy the main house with the best views of Smith Rock and the Cascade mountains. Smith Rock State Park is literally across the street. A great location for outdoor activities at the park or in the region. Hike, climb, bike, walk or jog around the park. Sip tea inside and watch the animals. Perfect for artist and photographers. Relax on the deck or enjoy a sunset BBQ with gorgeous views. Owners live in adjoining unit. Separate entrance. Instagram: @smithrockgardens DCCA Tax# 1784

Pointe of Blessing with hot tub and canyon views

Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South.

Smith Rock Nest - Steps to the Park!

No other home is closer to the Smith Rock's main attractions. ​The entire 3BR/2BA home in Terrebonne is yours for a perfect stay to maximize your Smith adventure! Enjoy the stocked kitchen, wood burning stove, central heat/AC, laundry, and hot tub. High speed fiber-optic internet and desk are provided for remote work. Discounts for week-long stays. Quick access to Bend (30 mins), Sisters (35 mins) and Mt. Bachelor (1 hour). No pets, no RVs, and no parties/events permitted. DCCA# 1715

Bend Country 4 BR/3 Bth, Amazing 9 Mt View, 9 acre

Plan your vacation getaway and escape the destination resorts at our quiet & peaceful lodge home retreat on 9 private acres just north of Bend, "in the country but not far away"; only 10 min. to restaurants & stores if you need anything. Relax while gazing at the amazing 9 Cascade Mts and overlooking a bend of the legendary Deschutes River. Enjoy some of the many Central OR area activities, Skiing, Golfing, Fishing, Hiking, Rock Climbing, Biking, local Wineries & Micro Breweries, & more.

Beach Bungalow in Prineville, OR

Bring the whole family to this great place with lots of room for fun. We welcome you to our stucco built Oasis in the high desert! Two roomy bedrooms with living room, full kitchen and laundry room, and bathroom with huge walk in shower. Private entrance and parking available. So much to do in the heart of central Oregon- stay for the rodeos, horse races, enjoy our quaint downtown, many outdoor activities, a short trip to the mountains and lakes. Come enjoy Prineville and stay with us! ❤️

Canyon House, Crooked River Ranch

Canyon House sits on the edge of the Deschutes River canyon and has a beautiful and scenic view of 11 mountains and peaks. Your home is a 2 bedroom and 2 bath 1450 sf manufactured home. It is attached to ours and Donna and I live on site family. Your privacy is my first rule and quiet is my second. Yet, you may see me watering plants or checking on the Spa. We are open for a 1 night minimum. Checkout time is strict to allow for cleaning and sanitizing on same day check ins.

Visit Rip’s Cabin in the Heart of Prineville

Experience the best of Central Oregon in this stunning 2017 downtown Prineville home! Ideal for families and traveling working professionals, this charming residence offers a convenient location within walking distance of restaurants and shopping. After a day of work or exploration, relax and marvel at breathtaking sunsets and stargazing opportunities. With easy access to Bend, Smith Rock, and the Painted Hills, this is the perfect base for both adventure and productivity.

Fallen Snag Lodge next to Smith Rock State Park

One mile from Smith Rock State Park & 30 minutes from Bend, Fallen Snag Lodge will be your very own private nature preserve. A wrap around deck faces the Marsupial rock formations & Crooked river, with lounge chairs set to view hawks, turkey vultures & eagles during the day & for stargazing at night. Ideal for couples or a family wanting to get away from it all in a beautifully appointed, comfortable lodge set in central Oregon's magnificent high desert landscape.