Holiday rentals with breakfast in Bend

Luxurious Private Tumalo Suite Nestled in Trees

The Treehouse Guest Suite is nestled in the trees in the beautiful community of Tumalo, Oregon! Tumalo, a short 10 minute drive west of Bend, is well known for its beauty to include easy access to hiking and biking trails. Your second floor craftsman style guest suite is surrounded by trees and includes a private entrance, garage, and deck. Our farm has scenic views of the Cascade Mountains. During the summer, guests can enjoy our English Country Garden, swimming pond, and Alpacas in the field.

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!

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.

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!

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.

Villa77: Renovated Stay Near Downtown & Old Mill

Newly renovated and thoughtfully designed, our airy apartment in Bend’s Midtown offers a 5-star experience. Enjoy crisp linens, plush towels, and fresh-ground local coffee brewed just the way you like it. Perfectly located near Downtown, the Old Mill District, and Bend’s best shops and eateries, our apartment is a cozy and stylish retreat. After a day of adventure, unwind in comfort at this charming home base! Owned by locals, this is the perfect launch pad for your Bend adventures!

Spotless Home w/ Mountain View & Private Garage

Experience Bend in comfort. Spotless, modern Yosemite inspired guest house that sleeps 4 with full kitchen, private driveway and garage, and gorgeous landscaping. Close to downtown, rivers, skiing, breweries, mountain biking, fishing, hiking, and all the outdoor fun Bend is famous for. Gorgeous view of the mountains and close to the lake basin. Perfect for a romantic getaway, outdoor enthusiasts, tele-workers, or families. Long term guests welcomed September-May up to 2 guests.

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.

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