Downtown Condo with Park Views, Outdoor Seating & Historic Charm

Drake Cottage 309 offers a distinctive Bend experience—nestled in a restored 1930s fourplex in the heart of downtown, this condo blends historic character with today’s conveniences. Enjoy immediate access to boutique shops, dining, arts, and Drake Park, all just steps from your door. Inside, you’ll find a thoughtfully updated retreat with plush furnishings, modern kitchen amenities, and high-speed WiFi. Private outdoor seating with park views and a fire pit table creates your own city sanctuary. Please note: as part of a vibrant multi-unit building at a bustling intersection, you may experience some urban energy and ambient noise, but city quiet hours and Good Neighbor Guidelines are in place to ensure a peaceful stay. Some amenities, such as laundry, are shared, and interim cleaning applies for longer stays—offering full transparency for a comfortable, memorable visit.

4 4 guests
2 2 bedrooms
1 1 bathroom
Bend Bend, Oregon
The image showcases the charming exterior of a lovingly restored 1930s fourplex in downtown Bend, Oregon. An arched trellis frames the inviting front steps, leading to a cozy porch perfect for morning coffee. The well-maintained, landscaped garden adds a touch of tranquility, with greenery and flowers enhancing the cottage's curb appeal.
Begin your Bend adventure at Drake Cottage 309—where a charming arched trellis, lush gardens, and a cozy porch invite you to relax and soak up the historic heart of downtown.

Prime downtown location with Drake Park views, historic charm blended with modern updates, private outdoor seating with fire pit and grill, fully equipped kitchen, free high-speed WiFi, and convenient shared laundry.

Historic Heartbeat: The Living & Dining Sanctuary

Features

  • • Plush seating
  • • Infrared fireplace
  • • High-speed WiFi
  • • Dining table
  • • Open to kitchen
  • • Adjacent to bedrooms

Step into a living space that hums with the spirit of 1930s Bend—gracefully restored to marry vintage character with modern comfort. The open-plan living and dining area is a cozy haven for unwinding after days spent exploring the city or the wilds beyond. Sink into plush seating by the flickering infrared fireplace, share stories over a home-cooked meal at the dining table, or stream your favorite show using the high-speed WiFi. The thoughtful layout and tasteful decor create a welcoming retreat that feels both historic and refreshingly up-to-date. While the urban energy of downtown Bend may pulse outside, inside you’ll find a calm, comfortable cocoon—your perfect base in the city.

A cozy living room featuring a comfortable sofa set around a coffee table, with a television, floor lamp, and a window letting in natural light. The decor blends vintage charm with contemporary touches, creating a space perfect for relaxing or socializing.
Relax in plush comfort by the window—perfect for cozy evenings and movie nights.
A warm dining area with a wooden table and chairs, viewed through an arched doorway that offers a glimpse of the adjoining living space. Natural light floods in, enhancing the inviting feel and sense of openness.
Share memorable meals in the inviting dining area, seamlessly connected to the living space.
A cozy dining table with chairs set under an arched doorway, adjacent to the kitchen with a refrigerator and a red microwave. The scene is ready for family meals or entertaining guests, exuding warmth and hospitality.
Gather around for stories and laughter at the welcoming dining table—ideal for meals and game nights.

Chef’s Nook: The Modern Vintage Kitchen

Features

  • • Refrigerator
  • • Stove
  • • Dishwasher
  • • Microwave
  • • Toaster
  • • Coffee maker
  • • Open to living and dining area

Channel your inner chef in a kitchen that respects the past while serving up every contemporary convenience. The fully equipped space comes with a refrigerator, stove, dishwasher, microwave, toaster, and coffee maker—everything you need to fuel your adventures or savor leisurely mornings. Whether you’re packing a trail lunch or prepping an intimate dinner, the kitchen’s efficient layout and thoughtful amenities make cooking a pleasure. And with groceries, cafes, and eateries just steps away, you’re always at the center of taste and convenience.

This image captures the heart of the kitchen, featuring a prominent refrigerator, a distinctive red microwave, and a countertop with a sink. The scene conveys a welcoming, functional space suitable for preparing meals, baking, and family gatherings. The setup highlights modern appliances integrated into a warm, vintage-inspired design.
A cheerful kitchen with modern appliances ready for your culinary adventures.
This image focuses on the stove and kitchen sink set against a wooden countertop. The mood is cozy and homely, with an emphasis on meal preparation and the warmth of sharing food with others. The vintage feel is enhanced by the classic design elements and muted tones.
A cozy kitchen nook perfect for savoring home-cooked meals.
A bright kitchen corner featuring a well-lit sink under a window with a small plant, a checkered backsplash, a wooden countertop, and a clock. The scene suggests morning routines, such as brewing coffee, and conveys warmth and thoughtfulness in design.
Start your day in a sunlit kitchen corner designed for comfort and convenience.

Private Retreats: Restful Bedrooms & Bath

Features

  • • King bed
  • • Queen bed
  • • Streaming TV
  • • Dresser
  • • Closet
  • • Bathroom with shower
  • • Separated from living area for privacy

After a day soaking in Bend’s lively downtown or conquering mountain trails, two restful bedrooms await. Each is thoughtfully appointed—one with a plush king bed and streaming TV, the other with a comfy queen, dresser, and ample closet space. Crisp linens, calming decor, and restorative vibes ensure a deep night’s sleep. The conveniently located bathroom offers a refreshing shower and all the essentials, so you start and end every adventure in comfort. Tucked away from the main living area, these spaces offer a welcome sense of privacy—even within the vibrant heart of the fourplex.

A cozy bedroom featuring a bed with geometric patterned bedding, a nightstand with a lamp, and a wooden dresser. Soft, warm lighting and minimal yet soothing decor create an inviting and restful atmosphere. The ample dresser and nightstand highlight practical storage features.
Unwind in a welcoming bedroom with plush bedding, calming decor, and ample storage for a restful night’s sleep.
A bright bedroom with patterned bedding, bedside tables with matching lamps, and a mirror on the door. Sunlight streams into the room, enhancing the comfortable and warm mood, perfect for relaxing or reading before bed.
Wake up to gentle sunlight in a peaceful bedroom designed for comfort and relaxation.
A bathroom with a clean bathtub, vanity, shower curtain, and fresh towels arranged neatly. The setting is calm and rejuvenating, conveying cleanliness and comfort—ideal for a refreshing shower or a relaxing bath after a day of adventure.
Start and end your adventure days with a refreshing shower or relaxing bath in the tranquil bathroom.

Bend at Your Doorstep: Outdoor Escape & Urban Vibe

Features

  • • Private outdoor seating
  • • Dining table
  • • Gas grill
  • • Fire pit table
  • • Shared laundry
  • • Accessible from main living area
  • • Shared amenities with fourplex

Step outside to your private seating area, where Adirondack chairs and a dining table invite you to linger with coffee or bask in the sun. Enjoy direct views of Drake Park and the river in downtown Bend. Fire up the gas grill for an alfresco meal, or gather round the fire pit table in the evening, swapping stories and enjoying the fresh air. While the fourplex’s shared laundry and community spirit connect you to local life, your outdoor space remains your personal vantage point for both tranquility and the buzz of city living. Expect a vibrant ambiance from the downtown location—embrace the energy, but rest assured: quiet hours keep things peaceful at night.

A tranquil view of a calm water surface bordered by colorful autumn trees, a walking path, and a green railing. The scene captures the essence of Drake Park, inviting visitors to enjoy peaceful moments by the water within the heart of downtown Bend.
Direct views of Drake Park and the river offer peaceful moments right outside your door.
A practical laundry area featuring a washing machine, dryer, and a utility shelf for organizing household items. The space is functional and conveniently accessible for everyday needs.
Shared laundry facilities add convenience while connecting you to the local community.
An inviting outdoor area with a shed, a tree, and a pathway, suggesting a tranquil, private space for relaxation or hosting small gatherings. The setting is peaceful, surrounded by nature.
Private outdoor seating lets you relax or entertain in your own peaceful corner of Bend.

Explore the Area

This exterior image features a couple walking beside two bicycles under tall trees, suggesting both the pedestrian and cycling-friendly nature of the area. The background hints at a vibrant, accessible community setting that aligns well with Bend’s walkable downtown experience.
Strolling and cycling through Bend’s lively, walkable downtown neighborhoods.
The scene shows two kayakers navigating a river framed by lush trees, capturing the adventurous spirit and access to outdoor recreation that defines Bend. The playful mood and connection to nature emphasize Bend’s blend of city energy and natural beauty.
Adventure awaits just steps from downtown—kayak the nearby river for unforgettable moments.
This image showcases the cottage’s entrance area with large windows, a door leading outside, wooden furniture, and soft natural lighting. The inviting setup connects the cozy retreat to the vibrant world just outside the door.
A welcoming entrance sets the stage for downtown adventures and cozy evenings in.

Downtown Bend at Your Doorstep

Immerse yourself in the vibrant, walkable heart of Bend! From Drake Cottage 309, you're just steps from a variety of boutique shops, art galleries, and renowned restaurants. Browse Main Street’s independent retailers, discover local art at At Liberty Arts Collaborative, or catch a concert at the Tower Theatre. In the evenings, the Galveston corridor comes alive with fantastic brewpubs, live music, and wine bars—ideal for craft beer and wine tasting enthusiasts. The unit’s prime location and historic charm offer both the energy of city life and a cozy, thoughtfully updated retreat to unwind in after a night out. Note: While the urban setting brings lively city vibes, Bend’s Good Neighbor Guidelines and quiet hours help ensure peaceful evenings.

A breathtaking winter landscape featuring a snow-covered mountain, a lone hiker traversing the frosted terrain, and a dramatic sunset sky overhead. The scene captures the possibility of outdoor adventure and serene moments in nature.
Experience tranquil winter walks and stunning mountain views just steps from Drake Park.
A serene lake bordered by pine trees, with majestic mountains rising in the background and a soft sky above. The environment is peaceful, inviting activities like hiking, birdwatching, or simply soaking in the view.
Immerse yourself in the serenity of mountain lakes and scenic trails near the Deschutes River.

Drake Park Adventures and Deschutes River Fun

Step outside and experience Bend’s outdoor playground! Drake Cottage 309 sits just across from Drake Park and the Deschutes River, providing easy access to hiking, biking, paddle boarding, and canoeing nearby. Start your morning with a stroll along the scenic river trail or launch a float from the nearby drop-in point. Festival season brings lively music and food trucks to Drake Park—perfect for spontaneous fun. The outside seating area overlooking the park is ideal for people-watching, bird spotting, or simply soaking up the mountain air after a day of adventure. Explore nearby trailheads for hiking and biking, or make the quick drive to the Old Mill District for more outdoor experiences. The park’s proximity means you can easily transition from urban excitement to natural beauty, all while enjoying the unique character of your historic home base.

This interior image features the cottage's inviting front door area, a large window for natural light, a comfortable sofa, a table lamp, and a stylish rug. The space is bright, cozy, and conducive to both relaxation and work, hinting at the ease of transitioning between productivity and downtime.
Bright, cozy entryway perfect for starting your workday or unwinding after hours.
Pictured is a tidy dining area with a wooden table, several chairs, eye-catching wall art, and an air conditioning unit. The setup is ideal for meals, informal work sessions, or reading, fostering a versatile environment well-suited to remote work needs.
Versatile dining table doubles as a productive workspace for remote professionals.
An exterior action shot captures a snowboarder mid-air against a snow-capped mountain and vibrant blue sky. The scene is lively and outdoorsy, evoking the spirit of exploration and adventure accessible near the cottage.
Outdoor adventure awaits just beyond your doorstep in scenic Bend, Oregon.

Work Remotely in Style & Comfort

For digital nomads and remote workers, Drake Cottage 309 combines historic ambiance with modern essentials. Enjoy free, reliable WiFi and a peaceful, comfortable space to focus—plus, you're just blocks from creative coffee shops like Lone Pine and Palate for productive work sessions or energizing breaks. Need a change of scenery? Drake Park offers tranquil spots for outdoor brainstorming or a quick midday recharge. The fully equipped kitchen and shared laundry access make extended stays effortless, while Bend’s downtown amenities are always within reach for after-work relaxation. Please note, some urban energy and ambient noise may be present due to the property’s prime central location and multi-unit setting. For longer stays (30+ days), interim cleaning is required to keep your workspace fresh and inviting.

A skier in a bright green jacket carves down a pristine snowy slope beneath a vivid blue sky, with distant mountain peaks adding dramatic scenery. The image conveys the excitement of winter sports and the natural beauty accessible from Bend.
Chase adventure at Mt. Bachelor's snowy slopes—just 21 miles from your doorstep.
A bright, inviting living room featuring a sofa, cozy rug, lamps, and a large window letting in natural light. The space feels welcoming, perfect for relaxing or socializing after a day of outdoor adventure.
Unwind in comfort—your cozy Bend retreat awaits after every adventure.

Year-Round Bend Experiences

No matter the season, Drake Cottage 309 is your launchpad for adventure. In summer, enjoy floating the Deschutes River, outdoor concerts, and exploring the famous Ale Trail. During winter, access skiing, snowboarding, and sledding at Mt. Bachelor just 21 miles away—then return to a cozy retreat with an infra-red fireplace and efficient heat pump. Fall and spring bring hiking, biking, and golf, with stunning foliage and mild temperatures. The property’s outdoor seating and fire pit table make for memorable evenings outside, any time of year. Embrace the unique blend of urban convenience and outdoor enthusiasm that makes Bend truly special!

Property Amenities

Facilities & Security

Fire Extinguisher

Outdoor Space: Patio

Fire Pit

Comfort & Lifestyle

Hair Dryer

Ice-maker

Dishwasher

Toaster

Clothes Washing Machine

Clothes Dryer

Stove

BBQ Grill

TV

Laundry Basics: Clothes Dryer, Clothes Washing Machine

Oven

Standard Essentials

Towels

Climate Control

Cooking Basics

Smoke alarm

Carbon Monoxide Detector

Bed Linens

High-Speed Internet

Shower/Bathtub

Cooking Space: Full Kitchen

Kitchen Basics: Basic Dishes & Silverware, Microwave/Convection Oven, Refrigerator

Ready to Book Your Stay?

Discover the unique blend of historic charm, downtown energy, and outdoor adventure at Drake Cottage 309—book your Bend getaway today!

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Cancellation Policy: Strict

Cancelation Policy

You can cancel this Vacay and get a Full refund up to 60 days prior to arrival

Important Information

Check-in and Check-out Procedures

  • City of Bend quiet hours are from 10pm to 8am and are enforced as are Bend's Good Neighbor Guidelines.
  • The Good Neighbor Guidelines are in the binder.

Property Access

  • This is a multi-unit building (fourplex) with some shared walls between apartments.
  • Some noise may travel between apartments, especially if doors and windows are open.
  • The property is situated on a busy intersection.
  • Access to shared washer and dryer provided.

Policies and Rules

  • No smoking allowed.
  • No pets allowed.
  • Maximum occupancy: 4 occupants. Children must be counted within the maximum occupancy unless they are under the age of two and are sleeping in a crib.
  • Minimum age: 25 years. The tenant named on the agreement/booking must be at least 25 years of age and will occupy the property during the entire tenancy.
  • Children allowed.
  • No events allowed.

Fees and Payments

  • For stays longer than 30 days, interim cleaning will be required at the renter’s expense (this charge is not included in the reservation price).

Utilities and Amenities Access

  • Utilities included.
  • Complimentary wifi access (high-speed internet).
  • Shared washer and dryer available.
  • Kitchen equipped with refrigerator, dishwasher, stove, oven, microwave, toaster, coffee maker, ice-maker, cooking basics, and basic dishes & silverware.
  • Outdoor fire pit table available.
  • Efficient wall-mounted heat pump for heat and air conditioning.
  • Infra-red fireplace is available.
  • BBQ grill available.
  • Patio and outdoor seating with dining table and chairs, plus Adirondack chairs.
  • Bed linens and towels provided.
  • Hair dryer included.
  • Shower and bathtub combination available.

Safety and Emergency Information

  • Smoke alarm and carbon monoxide detector present.
  • Fire extinguisher available.
  • The Good Neighbor Guidelines are in the binder.

Other Critical Details

  • Located on the downtown end of the Galveston corridor.
  • One block from the Galveston Bridge overlooking the river.
  • Across from Drake Park (Deschutes River float drop, festivals, and music).
  • 0.5 mile to Downtown Bend.
  • 1 mile to Old Mill District.
  • 18 miles to Redmond.
  • 21 miles to Mt. Bachelor.