Holiday rentals with breakfast in Bend

A majestic waterfall cascades down rocky cliffs, surrounded by lush greenery and tall trees. A winding creek flows through the foreground, with smooth stones scattered along its banks, leading the eye towards the waterfall in the background.

4.99 out of 5 average rating, 153 reviews

Creekside Studio

This Studio is nestled in the forest along side Tumalo Creek, 10 minutes west of beautiful Bend, Oregon.This is an upstairs studio. Come to unplug, unwind, and relax in this serene retreat! We are Creekside and a Studio. Animals are welcome BUT MAY NOT STAY IN THE ROOM UNATTENDED, THANK YOU. Winter months YOU MUST HAVE 4 wheel drive and studs or chains. Bring your cross country skis or snowshoes as you can play right outside your door. This is an Art Studio for local artist to show their work.

ValueFamilyWifi

4.99 out of 5 average rating, 373 reviews

A cozy living area features a comfortable gray sofa with colorful cushions and a wooden coffee table. Natural light fills the space through large windows, highlighting warm wooden accents. A flat-screen TV and bookshelf are positioned against the wall, offering convenience for relaxation and entertainment.

Guest suite 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!

LocationFamilyWalkability

A two-story apartment building is set against a vibrant blue sky, surrounded by lush greenery and landscaping. The structure features a warm color palette, with large windows and a wooden deck. A landscaped garden with various plants is visible in the foreground.

4.95 out of 5 average rating, 1254 reviews

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

Brand new remodeled apt 2025! 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 westside location. Walking easy to NW Crossing, Newport Market, Galveston, downtown Bend. Cycling routes just outside front door. Phils trails 2 miles. NOTE-28 steps up from street! NO pets allowed!

LocationFamilyLayout

Guest favourite

Apartment in Sunriver

Room With a View Condo, Sharc passes included.

Room With A View Condo has a rustic feel with exposed wood beams, tall ceilings, an open floor plan and a large cozy stone fireplace. This is the feel you want when you vacation to Sun River. Stunning views of the rolling hills, and the Oregon Cascade Range including Mt. Bachelor and Broken Top are visible from the living room, deck, and your king size bed. Conveniently located a short walking path to Sun River Lodge, and The Village. Wifi, cable, smart TV, and DVD provided. Fully stocked.

FamilyValueHot tub

4.93 out of 5 average rating, 190 reviews

Superhost

The home is located in a serene wooded setting, featuring a charming exterior with a metal roof. A paved driveway leads up to the front entrance, which is surrounded by a landscaped yard with gravel and natural elements.

4.85 out of 5 average rating, 171 reviews

Old Mill Cottage In Deschutes River Woods

A little piece of Bend's history in Deschutes River Woods. This adorable Mill Home was moved and remodeled in 2014. 2 bedroom 1 bath 1040 sq ft home. Kitchen is well equipped for cooking, baking, bbq, or take-out. The back yard paver patio has generous seating, bbq, table and umbrella for enjoying summer evenings. Garage has been converted to a game room with a pool table, ping pong, darts and bar style seating. 40 minute drive to Mt Bachelor ski resort and 10 minutes to downtown Bend.

LocationValueOutdoor spaces

4.98 out of 5 average rating, 127 reviews

A living area is presented with comfortable seating arrangements, including a sectional couch and a leather sofa. A large coffee table sits in the center, and a stone fireplace adds a rustic touch. A large screen TV is positioned nearby, with aquatic decor visible through a glass enclosure.

Guest suite in Bend

The Bird Pond

The guest suite is in the center of town, close to most everything. The space 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) 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.

ValueLocationShared spaces

4.97 out of 5 average rating, 312 reviews

Private 2Bd Duplex Family Friendly, Dog, 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

FamilyLocationLaundry

The exterior of the two-story apartment is framed by tall pine trees, showcasing a robust wooden structure. A private entrance and garage are visible, while a deck extends from the second story, offering an inviting extension of the living space.

4.97 out of 5 average rating, 124 reviews

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.

ValueFamilySleep quality

5.0 out of 5 average rating, 21 reviews

EV Charging*Private Hot tub*New Decor*

*New Management *EV Charging *Updated Furniture & Decor *Brand New (December 2025) Balconies *Brand New (December 2025) Hot Tub Forget your worries in this serene space overlooking the Deschutes River. The Mount Bachelor Village Resort has all the amenities. Access to the resort outdoor pool and hot tubs, in addition to your own private hot tub. Access to the River Trail. Drive Times: 5 mins to the Old Mill District 25 mins to Mt. Bachelor 45 mins to Smith Rock

FamilyLocationHospitality

Guest favourite

An inviting outdoor seating area features a modern fire pit surrounded by cushioned chairs, offering a cozy spot for gathering. A dining table is set for outdoor meals, and thoughtful lighting enhances the space under the covered patio, framed by lush trees.

4.97 out of 5 average rating, 127 reviews

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.

LocationFamilyLayout

A modern kitchen and dining area are highlighted, featuring stainless steel appliances and sleek cabinetry. A wooden dining table accommodates four, positioned near a comfortable sofa. Natural light enters through windowed walls, enhancing the spacious layout and creating a welcoming environment.

4.97 out of 5 average rating, 119 reviews

Close to Downtown, Sparkling House with a View

Experience Bend in comfort. Spotless, modern Yosemite inspired guest house with full kitchen, private driveway/garage, and gorgeous landscaping. Close to downtown, rivers, skiing, breweries, mountain biking, fishing, hiking, and all the outdoor fun Bend is famous for. Winter view of the mountains. Perfect for a romantic getaway, outdoor enthusiasts, tele-workers, or families. Long term guests welcomed, up to 2 people and 2 vehicles.

FamilyLocationAccess

A spacious bedroom features a black metal bed frame with crisp white linens and layered decorative pillows. Nightstands with lamps are positioned on either side of the bed, and artwork adorns the walls. Natural light spills in from a nearby window, creating a bright atmosphere.