Holiday rentals with breakfast in Bend

Private Apartment, Separate Entrance, Spacious

DCCA License #001537 Welcome to the Garden Sweet, a private apartment adjacent to a residential home. Tuscan style living nestled on a beautiful acre. Private and peaceful, yet just minutes to great local dining, shopping and outdoor recreation. The historic downtown and river are an easy 6 minute drive into the heart of old Bend. Spacious 3 room suite-living makes longer stays comfy! No shared interior spaces. Our extensive gardens, gazebos, grills, firepits are shared and open for guest use!

Simple Serenity | Homey Pet-Friendly Wooded Haven

Welcome to Simple Serenity! Set against a lava flow, off the beaten path, our 1,200 square-foot guest suite has 2 bdrms, family room, kitchen with stove top & bathroom with laundry. Just 28 miles to Mt. Bachelor & 8 miles to downtown Bend, Simple Serenity is ideal for those who enjoy nature. Across the highway from the High Desert Museum and less than a mile from nearby trails, Simple Serenity is a short drive from lava caves, Sunriver, and numerous other activities. Bring your fur babies, too!

Beautiful 10 acre farm stay in Tumalo!

Welcome to our family farm! Our lodging consists of a beautifully remodeled private wing and secluded patio and a beautiful, private fire pit to enjoy after a long day hiking or skiing! We also have added a Swedish barrel sauna with hot rocks to enjoy. It does wonders for your skin and soul! We provide luxurious robes!Our working farm is located on a quiet country road, sandwiched between Bend and Sisters. We also are now booking our outdoor space for small weddings and other celebrations.

Jefferson Hideaway Unit #3

The Hideaway is a cozy, private studio for a family of four, featuring its own entrance for an exclusive stay. Designed for comfort, it offers high-quality features and thoughtful details. Its unique style adds warmth and charm, creating a welcoming retreat. Nestled in a quiet, picturesque neighborhood, it provides a peaceful setting for relaxation. While private, it shares a wall with the Alpine Modern unit, with a locked door managed by the property if rented separately, ensuring privacy.

Private Bend Retreat * Convenient East Side Gem

Perfect Spot for your trip to Bend! A wonderful house nestled in a quiet neighborhood. All newly furnished with high end furnishings with comfort and style in mind. Fenced yard, playhouse for kids, large deck and BBQ, corn hole, Central A/C Heat, 50 in TV w/ Roku, DVD player and Wii. Close to Hospital, Downtown, Food carts, breweries, pine nursery sport park/dog park. Quick easy access to Hwy 20 and 97, and Mt Bachelor. Local shopping at Costco, Whole Foods, Safeway, just down the road.

Blinn's Landing: Riverfront Cabin, Mountain Views

Book early for Summer 2025! Historic log cabin, located at the confluence of the Spring and Deschutes Rivers, adjacent to Sunriver Resort, offers a relaxing getaway with sparkling natural springs and picturesque mountain & river views. Enjoy an idyllic retreat at this coveted six acre homestead surrounded by the Deschutes National Forest and boasting 780 feet of private pristine riverfront perfect for fishing, river floating, hiking & stargazing. Wonderful work/play escape. Dogs welcome.

Cozy 2Bd Duplex Family Dogs firepit with yard

• The Wildflower Weekender is a comfortable Bend Duplex in a quiet, established neighborhood. • 30 min to Mt Bachelor • 50 min to HooDoo • You will be close to everything including both Highway 97 and 20. • The house is bright and cheery with all amenities to relax, work, or play. The decor does change seasonally to fit B•E•N•D NO PARTYING! *Quiet at 10pm* * Please note, this is a mountain town & weather is not a reason we can accept cancellations * *$50 flat dog fee

Spring River Guest Apartment

Beautiful second story apartment with private entrance, private heated garage and shop to prepare your equipment to hit the mountain! You will enjoy the calming surround of the Spring River and Deschutes national forest. The apartment is 5 minutes from Sunriver Village where you can find restaurants, supermarket, coffee shops, etc. Mt. Bachelor is 20 min away! Bike and hiking trails just down the street! Electronic locks for easy check-in and enhanced cleaning procedures.

Home With Mountain View

Experience Bend in comfort. New, modern Yosemite inspired guest house with full kitchen. Close to downtown, rivers, skiing, breweries, and all the outdoor fun Bend is famous for. Gorgeous view of the mountains and close to the lakes basin. Perfect for a romantic getaway, outdoor enthusiast, or a family. Queen bed in the master and living room includes a comfortable queen sofa bed. Tele-work and long term stay friendly! (maximum of 2 people for stays of 28 days+)