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Dog-Friendly Ranch Cottage w/ Yard ~ 13 Mi to Bend

A peaceful, private retreat awaits in rural Bend at the Honest Dog Ranch! ‘The Bunkhouse’ is a 3-bedroom, 1-bath cottage nestled beside the Oregon Badlands Wilderness, offering direct access to marked trails, natural sites and abundant wildlife. The ranch is rich in history and art, with authentic architecture and one-of-a-kind paintings. Enjoy Cascade Mountain views and serene surroundings at this high-desert hideaway, only 30 minutes from the breweries, boutiques and eateries in Downtown Bend!

Quiet central Oregon desert retreat with a view!

Bright and cheery cottage on five acres with a view! Bathrooms completely renovated in 2019 with tile and modern barn decor. Premium linens and duvets. Fully stocked kitchen with Nespresso machine. Gas BBQ on the deck! Relax in this extraordinary high desert setting or hike right out your front door. Located in a rural area 50 minutes north of Bend, between the Deschutes and Crooked Rivers, you will have access to climbing, fishing, kayaking. Come visit the craft breweries in nearby Redmond!

The Blackberry Cottage

This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.

Painted Hills Cottage - Perfect Getaway/Sanctuary

The Painted Hills Cottage is a lovely private 2.5 bedroom house surrounded by a lush floral garden. This unique and charming cottage is perfect for a family vacation or a gathering of friends. Free wifi, AC, outdoor BBQ, whimsical nooks and corners, art, flowers, magic, and only 15 minutes away from the famous Painted Hills! Pets?? We welcome pets but REQUIRE a $25/dog/night PET FEE (regardless of size) to be paid via cash on the day of arrival! All pets must be declared prior to arriving!

Immaculate, secluded Downtown Cottage-EV charger

25 time Airbnb "Super Host" award. 2017/2019 Winner of a "Certificate of Excellence" Rated as “Exceptional” 5 Star reviews for all vacation rentals in the Bend area. The Cottage is constantly being updated including new furniture, appliances, paint, and even painting of the cabinets. A new mini split A/C and Heating system will be installed in August, 2025.These significant investments keep the Cottage fresh and like it was new. City of Bend Short Term Rental Operating License: STR-20-

Old Town Bend Cottage | Walk to the Best of Bend

Experience the "Sweet Spot" of Bend. This 110-year-old logging-era cottage is perfectly tucked into Old Bend, offering a rare blend of historic soul and modern luxury. A 1/2 block from the Bend Surf Park and a short, scenic stroll from the Old Mill District and Downtown shopping & dining. Whether walking the famous Bend River Trail or to Drake Park, catching a concert at the Amphitheater, or hopping on the Mt. Bachelor bus, this heritage home is the ultimate basecamp for the best of Bend.

Contemporary Chic, Walk Downtown, Gourmet Kitchen

Featuring classic cottage charm with a contemporary modern twist, The Modern Mill Cottage perfectly embodies the spirit of Bend. This charming two bedroom, one bathroom vacation home is ideal for those Bend explorers who wish to be in the heart of it all. This house is located on a vibrant and eclectic street, situated just two blocks from downtown Bend. You are just a short stroll to all the superb dining, infamous breweries, art galleries, and festivals that make our town so unique.

Blossom Cottage Studio

Keep it simple and take it easy at this peaceful and centrally-located, unique, cozy getaway. The Blossom Cottage Studio is located in a beautiful garden setting. ~The space~ • One Room Studio • 1 Bathroom • Full sized bed (additional cot if needed) •Kitchenette (Refrigerator w/small Freezer, Toaster Oven, Microwave, Blender, Kuerig, etc) •Short walk to the heart of downtown Redmond. The cottage is private and located on the back property of a Gift Boutique Shop and Bakery/Cafe.

Historic Old Bend Cottage & Carriage House Spa

This historic Old Town Bend cottage boasts a relaxing setting for unwinding with a lovely cedar hot tub & sauna in its restored carriage house. Walk to the attractions: 0.2 mi. to the best shops and restaurants, and 0.4 mi. to Mirror Pond & Drake Park! Split heating in each room, snow gear storage, boot warmer, grill, and new washer/dryer. Driveway and extra street parking (free). Fast WiFi and a smart TV. The kitchen is fully stocked, and we look forward to hosting you!

Vintage Pink Hot Tub✓ Walkable✓

Our 105 year-old lovingly restored 1920 cottage is 3 blocks from First Street River Rapids, 25 minutes to Bachelor & 10 minute walk to Town. Centrally located urban setting on a main street. Step back in time, the original charm was painstakingly preserved, with original claw foot with shower and bathtub (which requires adequate mobility) and wood floors. Comforts include: Hot Tub, Gas fireplace, Dishwasher, W/D.

Adorable West Side Cottage, Pet Friendly!

Enjoy a cozy and comfortable stay in my 1-bedroom, 2-bathroom home, complete with a bonus room that offers plenty of privacy when needed and a plush futon that allows for two additional guests (best for up to 3 adults or 2 adults and 2 kids, or two couples would work as a well ) Conveniently located within walking distance of Newport Market, Backporch Coffee, Chow, and Spork, it's just five blocks from downtown

Stylish Downtown Cottage, Walk Everywhere

Escape to our newly renovated, pet-friendly historic cottage, just one block from Downtown Bend! This stylish 2-bedroom retreat comfortably sleeps four and blends old-world charm with modern luxury. Features include a gourmet kitchen, ultra-fast Wi-Fi, and AC. Enjoy the convenience of walking to Bend's best shops, restaurants, and breweries from your private getaway with free parking.