Treetop Cottage ~ Westside Bend ~ Views + Bikes

A charming craftsman cottage perched above Bend's coveted Westside — treetop views from every window, open-concept living with gas fireplace, soaking tub, and natural gas BBQ. Walk to local favorite eateries, shops, and parks within minutes. 3 bedrooms, 2.5 baths, complimentary cruiser bikes included. This is your quintessential Bend retreat.

Tucked into the treetops of Bend's beloved Westside, Treetop Cottage is a charming craftsman home where sweeping southern treetop views, a cozy gas fireplace, and a soaking bathtub set the tone for a genuine Bend escape. Three bedrooms, two and a half baths, complimentary cruiser bikes, and a walkable location that puts Bend's best restaurants, coffee shops, and breweries right outside your door. Classic Pacific Northwest charm — with every modern comfort already taken care of.

The Space
At 1,744 square feet across three stories, the home has been thoughtfully updated by a local designer who understood the assignment: honor the Pacific Northwest cottage character while bringing it fully into the modern era. Hardwood floors, handmade pottery curated by the owners, a gas insert fireplace, and a sliding glass door that opens to a deck with treetop views — it all adds up to a space that genuinely feels like a retreat, not a rental.

Living Room & Kitchen: The heart of the home is an open-concept second floor where the living room, dining area, and kitchen flow together without interruption. Hardwood floors run throughout, the kitchen is stocked for real cooking with stone tile countertops and locally made pottery details, and the dining table seats six comfortably. The living room anchors around a gas insert fireplace and a flat-screen TV (app access only, no cable)— but honestly, the sliding glass door to the treetop deck is the real focal point. That view never gets old.

Primary Suite: The third floor primary suite is an oversized, light-filled sanctuary with soaring treetop views, a massive walk-in closet, built-in bookshelves, and a plush club chair and ottoman that were clearly designed for long afternoons with a good book. Two rollaway cots with memory foam mattresses are available for extra guests — just request them in advance. The ensuite spa bathroom features a dual vanity, deep soaking tub with jets, and a separate walk-in shower.

Bedroom 2: A charming queen bedroom on the third floor with a pine bed frame, closet, and views to the side and backyard.

Bedroom 3: A queen bedroom on the second floor — convenient, comfortable, and ideal for guests who prefer easy access to the main living areas.

Bathrooms: The ensuite primary bath anchors the third floor with its soaking tub and walk-in shower. A full tub/shower combo bath also sits on the third floor adjacent to the laundry room. A powder room on the second floor keeps morning routines running smoothly for the whole group.

Outdoor Living

The Front Deck: Step outside and you immediately understand the Treetop Cottage name. This deck offers sweeping southern views over a canopy of trees with two cushioned chairs — the kind of spot that turns a morning coffee into a full hour and a sunset drink into something worth remembering.

Backyard: The back patio is ready for a proper Bend evening — natural gas BBQ, outdoor dining table, and café string lights overhead. The backyard has a wild, wooded Pacific Northwest feel: no manicured lawn, just natural terrain, mature trees, and a peaceful quiet that reminds you why you left home in the first place. It is fully fenced to keep your kids nearby.

Prime Westside Bend Location

Treetop Cottage sits a couple of quiet residential blocks above the action — close enough to walk everywhere, far enough to feel like a genuine escape. Leave the car parked and explore on foot:
- Chow (Bend's iconic brunch spot) — 0.2 miles / 4-min walk
- Nancy P's Bakery & Cafe — 5-min walk
- Newport Market (beloved local grocery) — 5-min walk
- 10 Barrel Brewing — 0.7 miles / 13-min walk
- Galveston & Newport Corridors — 5–15 min walk (breweries, boutiques, gear shops, coffee & more)
- Downtown Bend — 0.9 miles / 18-min walk
- Old Mill District — 2.5 miles / short drive or bike
- Mt. Bachelor (skiing, snowboarding, mountain biking) — 30 min / 21.8 miles
- Redmond Airport (RDM) — 23 min / 17 miles
Two complimentary cruiser bikes (bring your own helmets) with lock and pump are waiting in the garage — ideal for exploring without using a drop of gas.


Why Families Love Treetop Cottage
Treetop Cottage has a way of working for everyone in the group, especially families with young travelers.

The bedroom arrangement allows for privacy, while still keeping the kids close. The rollaway cots (must request in advance) with memory foam mattresses in the primary suite mean you can bring the littlest ones in without sacrificing comfort.

The open second floor is made for togetherness. Movie nights by the fireplace, board games at the dining table, big breakfasts cooked in a kitchen that naturally brings everyone into the same space without it ever feeling cramped.
The Westside location is a family's dream. Newport Market is a five-minute walk for forgotten items and impromptu snack runs. Chow is four minutes away for an amazing brunch. The Galveston corridor has ice cream, coffee, and every kind of takeout you could want. And when adventure calls, Mt. Bachelor is 30 minutes away and the Deschutes River Trail is an easy bike or drive.
The backyard gives kids room to breathe. The wooded, natural terrain is a genuine Pacific Northwest outdoor experience — not a groomed lawn, but the kind of wild backyard that sparks imagination.

Perfect for:
Families with kids looking for a walkable, character-filled Bend home base
Couples or small groups seeking a peaceful Westside retreat
Foodies and coffee lovers — Some of Bend’s best restaurants and coffee shops are steps away
Ski and snowboard trips to Mt. Bachelor (30 minutes away)
Remote workers who want a beautiful, quiet space with fast WiFi
Longer stays — in-unit laundry, a fully stocked kitchen, and a layout built for living comfortably

What’s Included:
- 3 bedrooms — king primary suite + 2 queens (plus 2 rollaway cots with memory foam, on request)
- 2.5 bathrooms — soaking jetted bathtub, walk-in shower, dual vanity in primary ensuite
- Gas insert fireplace in the living room
- Fully stocked kitchen — cookware, dishes, glassware, utensils
- Natural gas BBQ + outdoor dining under café lights
- 2 complimentary cruiser bikes with lock and pump (bring your own helmets)
- In-unit washer and dryer with detergent + drying rack
- Flat-screen TV with app access
- Central heat and A/C
- All bed and bath linens, towels, and soaps
- Professionally managed by Sojourn Homes — local, responsive, and available 24/7
Every Sojourn Homes property is professionally cleaned, inspected before each stay, and backed by a local team that genuinely cares about your experience. If something comes up during your trip, we're always just a message away.

Book Your Westside Bend Getaway
Whether you're planning a family ski weekend, a long overdue friend trip, or a slow week in one of Oregon's most beloved cities, this is the Westside Bend retreat that will make you want to come back every year.
Reserve your dates and come see why Treetop Cottage guests keep returning. Bend is better from up here.

Good To Know:
- No pets allowed.
- This is a shoe-free home, please leave shoes in the tiled entry
- Steep driveway from Quincy Ave: low-clearance vehicles may bottom out on entry. All guests must park inside the garage (shared driveway — parking on driveway blocks neighbor access). Or free street parking readily available nearby.
- Multi-level craftsman with two interior flights of stairs plus entry steps — not recommended for guests with significant mobility limitations.
- Completion of a Rental Agreement, including guest verification, is required for all bookings before check-in instructions are released.