Holiday rentals with breakfast in Deschutes River

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!

Family · Value · Long stay

Palm VlLLA on Mt Tabor ~ a/c ~ Small+Stylish!

Quality & Design in a smaller space Entirely to Yourself! Escape into your Oasis 🌴 Centrally Located in one of Portland's best Neighborhoods at an affordable price ✓ ⚜️ Includes ☕ STARBUCKS COFFEE, Tea & an Oatmeal Breakfast ⚜️ LUXURIOUS Stearns & Foster Mattress fit for a Queen 👑 ⚜️ ARRIVE ANYTIME! to your own PRIVATE ENTRANCE with 🔑 LOCK BOX ⚜️ KITCHENETTE: Refrigerator, Microwave, Mr Coffee, Water Kettle, 🥂 Wine Glasses & More! ⚜️ KOI POND in the Tranquil, Lush Tropical Gardens 🌴

Value · Location · Hiking

Country Living in a Forest Setting

Come stay in your own cozy mini apartment, a little over 25 minutes from the Portland suburbs, and about 45 minutes from downtown Portland. Our home sits on two wooded acres. You'll have a private deck, private bathroom, private entrance, and private living space. There is a queen bed in the bedroom and a futon/sofa in the living area that makes a shorter twin-size bed. Check-in time is after 4 pm. Early check-in is possible, just contact us. No Smokers! One pet on approval, up to 45lbs.

Family · Value · Indoor spaces

Luxury Glamping: Creek-side, Soaking Tub, Alpacas

Welcome to Handsfull Farm’s 'Creek-side Retreat' — private family-run glamping on a working 50-acre Oregon farm, 90 min from Portland • Heated queen bed, his-and-hers warmers, tent heat, AC • Outdoor hot soaking bathtub 10ft from Mill Creek—soak under the stars • Private flushing bathroom, outdoor shower, plush robes • Outdoor kitchen stocked: farm-fresh eggs, pancake mix, coffee • Friendly alpacas, goats, chickens, no road noise, no hidden fees *Two nights recommended for the full experience*

Value · Family · Bathroom

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!

Family · Value · View

Cozy Guest Cottage in Woodstock Neighborhood

A bright and cozy cottage located near Reed College, Woodstock's restaurants/coffeehouses, Trader Joe's and public transit. This residential neighborhood is ideal for a quiet retreat for all visitors. The private guesthouse is outfitted to make your stay comfortable including a spacious bathroom with a walk in shower and a heated floor. Plus, you may want to enjoy a cup of coffee on your patio located behind the Airbnb. As an added bonus, breakfast items and home baked treats are provided.

Location · Value · Indoor spaces

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.

Family · Value · Accuracy

Private Laurelhurst Studio With Hot Tub/Patio!

Our house is right off the Hollywood Light Rail stop in Laurelhurst, a beautiful historic neighborhood. Our studio, which is connected to our main house (still very private), steps through french doors out to a patio with barbeque and hot tub. It includes a mini fridge, Keurig with compostable cups, and microwave. We are walking distance to great restaurants, Trader Joe's, vintage, coffee shops, pubs, Laurelhurst Park, and 24 hour fitness. Catch the farmer's market on Saturday mornings!

Family · Location · Amenities

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.

Family · Location · Kitchen

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!

Location · Family · Walkability

Palmer's Cabin on Mt Hood, Hot Tub & River Access!

A cozy log cabin, nestled in a grove of Douglas Firs on the Mt. Hood Corridor. A 5 minute walk to the Sandy River, less than 1 mile to Highway 26. Covered front porch, large back deck with BBQ, firepit (seasonal). Private hot tub surrounded by woodlands. 2 full bedrooms, one bonus sleeping room with a single bed. Couch and two recliners. 1.5 Bath, full kitchen, gas fireplace. 2 tvs, WIFI, Netflix, Apple TV, a collection of DVDs board games, poker set. STR REGISTRATION # PENDING.

Value · Family · Barbecue

Luxury Guesthouse | Spa Bath + Private Patio

A private design-forward luxury guesthouse in walkable Laurelhurst, just minutes from downtown Portland. ☀ 10 Mins to downtown + Airport ☀ Free private on-site parking ☀ Luxury queen bed • premium bedding ☀ Fully stocked chef's kitchen ☀ Private covered patio + fire pit | BBQ ☀ 65” 4K Smart TV + fast Wi-Fi ☀ Spa shower + heated bathroom floors ☀ Safe, walkable restaurants, coffee & transit ☀ Bikes to explore Portland ★ Your Luxury Oasis in the city awaits you!

Value · Family · Solo travel