Holiday rentals with breakfast in Bend

4.99 out of 5 average rating, 185 reviews

Guest suite 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.

4.97 out of 5 average rating, 216 reviews

Midtown Mid-Century With Hot Tub Near Downtown

POWDER SKI SPECIAL - SAVE 20+% NOW This fully updated 1940s, stocked and furnished home perfectly fits everyone. (Please read rave the reviews.) Central Oregon is the ultimate vacation destination with 25 golf courses, 22 breweries, 14 lakes, Mt. Bachelor, Deschutes River, Newberry Crater, Badlands Wilderness, hiking, waterfalls, wildlife, fishing, skiing, music, festivals, numerous activities, arts/culture, shopping, dining experiences, family-friendly, dog friendly...the options are endless!

4.95 out of 5 average rating, 1,179 reviews

Flat in Bend

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

Brand new remodeled apt January 2024! 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, 20 minutes to winter sports. NOTE-28 steps up from street! NO pets allowed!

4.99 out of 5 average rating, 252 reviews

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!

5 out of 5 average rating, 127 reviews

Flat in Bend

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

4.94 out of 5 average rating, 248 reviews

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.

Superhost

Townhouse in Bend

5 out of 5 average rating, 3 reviews

3 Townhome Apts, 1 Bldg. Modern, Updated, Clean!

Fantastic for large groups, family events and gatherings! 3 separate apartments in same building. 2 level townhomes, each w/ 2 bedrooms and 2.5 baths for a total of 6 bedrooms, 6 full baths and 3 half baths. Plenty of parking with 3 garage spaces, 3 driveway spaces along with street parking. Each unit has 2 br's upstairs, with en suite baths. All 3 units are virtually identical in layout, with similar decor. Located in Boyd Acres, just minutes to downtown and everything Bend has to offer.

4.96 out of 5 average rating, 106 reviews

Home With Mountain View

Experience Bend in comfort. New, modern Yosemite inspired guest house with full kitchen that comfortably sleeps 4. 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+)

5 out of 5 average rating, 47 reviews

Cabin in Bend

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.

Superhost

4.88 out of 5 average rating, 181 reviews

King Bed - Pet Friendly - 3 Bedrooms 2 Bathrooms

Jameson's Place is located minutes from the Old Mill District, the Hayden Homes Amphitheater, Deschutes Brewery, and the Mount Bachelor ski area. The Smith Rock State Park is a short 45 min drive to the North and Crater Lake National Park is a 2-hour drive to the south. Jameson's Place (named after my son) is a great space for families with small children and/or pets. The private fully fenced backyard is a wonderful space to play cornhole after a long day of exploring Central Oregon.

4.97 out of 5 average rating, 192 reviews

Flat in Bend

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!