Holiday rentals with breakfast in Redmond

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!

The Bird Pond

The guest suite is in the center of town, close to most everything. The studio has a separate bathroom and laundry room/kitchenette. Patio in the fenced backyard features a small pond that attracts many birds. There is a large screen TV with cable (including sports) Netflix and Prime Video. The queen Murphy bed has a Purple mattress. There is a small refrigerator, toaster oven, microwave, Kuerig and kettle. Breakfast is provided. An ice chest is available for loan as well as river towels.

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!

Private apt, 1bdrm/1bath, with kitchen, in town

Brand new remodeled apt 2026! 1 king bed, 1 bath/shower with living/dining/bdrm/full kitchen apt. Private entrance. 3 bright, light & spacious rooms, treetop views. Kitchen has new full-size induction range and refrigerator, plus all cooking essentials. All new flooring/furnishings. Deck. In town location. Walking distance to NW Crossing, Newport Market, Galveston, also downtown Bend. Cycling routes just outside front door. Phils trails 2 miles. NOTE-28 steps up from street! NO pets allowed!

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.

2Bd Duplex Family Oasis Dogs firepit fenced 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.

Family/Remote Work Friendly House in Bend OR

Welcome to the "Cascade Chalet", perfect for a family or friend's getaway. Relax in the tranquil backyard while the ponderosa pines whisper above. At night, enjoy the warm fire, while gazing at the constellations under a cozy blanket. You're 30 minutes from Mt. Bachelor, 8 minutes to Phil's Trailhead and walkable to downtown. The back door leads to a spacious yard with plenty of seating and a large outdoor green space, grill, gas fireplace and kids play area.