See all properties
Condo

Historic Drake Cottage - Walk to Downtown Bend - Drake Park Across the Street - Perfect for Couples

Condo with kitchen, near Old Mill District

Photo gallery for Historic Drake Cottage - Walk to Downtown Bend - Drake Park Across the Street - Perfect for Couples

Efficient and functional living space with great flow. Kickback and watch the game, snacks are just a few steps away!
A great night's sleep is what it's all about after a day of exploring Central Oregon.
This cute little patio set and grill sit right outside the front of your cottage
Exterior
Your view across the street of the Deschutes River

Reviews

9.6 out of 10
Exceptional
1 bedroom1 bathroomSleeps 246.5 sq m

Popular amenities

  • Air conditioning
  • Outdoor space
  • Fireplace
  • Barbecue grill
  • Kitchen

Explore the area

View map
Bend, OR
  • Place, Downtown Bend Business Association
    ‪10 min walk‬
  • Place, Old Mill District
    ‪15 min walk‬
  • Place, Hayden Homes Amphitheater
    ‪15 min walk‬
  • Airport, Redmond, OR (RDM-Robert's Field)
    ‪25 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Master

1 King Bed

1 bathroom

Full Bathroom #1

Spaces

Deck or patio
Kitchen

About this property

Historic Drake Cottage - Walk to Downtown Bend - Drake Park Across the Street - Perfect for Couples

Drake Cottage 311 – A Charming Downtown Bend Getaway

Welcome to Drake Cottage 311, an adorable one-bedroom retreat in the heart of historic downtown Bend. Nestled in a beautifully restored 1930s fourplex, this cozy 500-square-foot apartment is perfect for couples or solo travelers looking to experience everything Bend has to offer—all within walking distance!



Unbeatable Location & Walkability

With a Walk Score® of 86, this prime location puts you at the crossroads of all things happening in Bend:

✔ Across the street from Drake Park, where you can stroll the riverfront, catch a free Munch ‘n Music event, or watch tubers float down the Deschutes River

✔ Just a couple of blocks from downtown, where you’ll find award-winning restaurants, boutique shopping, art galleries, and craft breweries

✔ Steps from street festivals, live music, art fairs, and Tower Theater events happening year-round

✔ First in line for the downtown farmer’s market in the summer



Cozy & Inviting Space

Drake Cottage 311 is the mirror twin of Drake Cottage 307, but designed to sleep two comfortably. Thoughtfully updated while maintaining its historic charm, this cottage blends modern comforts with vintage character—offering the perfect Bend retreat after a day of adventures.



Explore the Galveston Corridor & Beyond

Just one block from the Galveston Bridge, you’re moments from Bend’s most vibrant food and drink scene:

✔ Brewpubs & food carts serving up local flavors

✔ Cozy coffee shops perfect for a morning pick-me-up

✔ Easy access to the Deschutes River, hiking trails, and the Old Mill District



Your Home Base for Bend Adventures

Whether you're sipping craft beer, biking along scenic trails, or enjoying live music, Drake Cottage 311 puts you in the center of it all while offering a peaceful, stylish retreat to come home to.



Book your stay today and experience the best of Bend from this perfectly located downtown gem!



Patio

- Gas Grill

- Outside seating looking out at Drake Park. Dining table & chairs, plus Adirondack chairs



Kitchen

- Fully equipped kitchen with new appliances

- Fully stocked with utensils for both the cook and the baker

- Eat-in kitchen with dining table

- Cold water filtration system



What Else?

★ Located on the downtown end of Galveston corridor

★ Masterfully updated living space, blending vintage charm with modern convenience

★ Free wifi access

★ Outdoor fire table

★ Efficient wall-mounted heat pump for more heat in the winter and A/C in the summer

★ Infra-red fireplace

★ HD SmartTV and BluRay with streaming content (no cable)

★ Updated bathroom with shower and tub

★ Off-street parking for one vehicle

★ Fantastic Historic Downtown Bend location: Walk Everywhere!

★ Locked storage available for your gear



Location:

★ 1 Block from Deschutes River Trail and Deschutes River

★ 4-5 Blocks to Old Mill restaurants, shopping, and entertainment

★ 3/4 Mile to Hayden Homes Amphitheater

★ 1.5 Miles to Drake Park

★ 15 Miles to Sunriver

★ 20 Miles to Mt.Bachelor



ACTIVITIES

- Hiking

- Biking

- Skiing & Snowboarding

- Sledding

- Snowmobiling

- Paddle Boarding

- Tennis

- Kayaking

- Golf

- Canoeing

- Floating/Tubing

- Wave-riding

- Bird Watching

- Fishing

- Ale Trail

- Shopping

- Dining

- Cascade Lake Byway

- Concerts

- Brewery Tours & Tasting

- Wine Tasting

- And More!



Additional Property Information:

Keep in mind this is a multi-unit building. Each of the apartments in this wonderful fourplex home feels quite private but they do have some shared walls. Please be aware that some noise may travel between apartments, especially if doors and window are open. City of Bend quiet hours are from 10pm to 8am and are enforced as are Bend's Good Neighbor Guidelines. Thank you for respecting our neighbors and helping everyone enjoy this peaceful retreat in Bend. The Good Neighbor Guidelines are in the binder.



NO SMOKING allowed at this property.

NO PETS allowed at this property.

No on-site laundry.



Maximum occupancy: 2 Occupants – Children must be counted within the maximum occupancy unless they are under the age of two and are sleeping in a crib.



Tenant Requirements: Tenant stated on the Agreement/Booking must be at least twenty-five (25) years of age and acknowledge that they will occupy the Property during the entire tenancy.

Add dates for prices

Amenities

Kitchen
Air conditioning
Outdoor space
Barbecue
Fireplace

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Home sweet home. Private entrance with your own grill. Patio looks out onto Drake Park with the Deschutes River running alongside.
Perfect Couples Getaway! Walk to Dwntwn, Galveston Corridor & Drake Park, Parking, Air Conditioning
  • Kitchen
  • Air conditioning
  • Outdoor space
  • Barbecue grill
9.8 out of 10, (105 reviews)
Perfect Couples Getaway! Walk to Dwntwn, Galveston Corridor & Drake Park, Parking, Air Conditioning

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Noise-free guestrooms cannot be guaranteed
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Bend

Located in Old Bend, a neighbourhood in Bend, this condo is in the mountains. Deschutes Brewery and Regal Old Mill are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Sun Mountain Fun Center and Bend Rock Gym. High Desert Museum and Petersen Rock Garden are also worth visiting. Canoeing offers a great chance to get out on the surrounding water, or you can seek out an adventure with cycling, mountain climbing and hiking/biking trails nearby.
Map
Bend, OR

What's nearby

  • Drake Park - 1 min walk - 0.0 km
  • Downtown Bend Business Association - 10 min walk - 0.8 km
  • Old Mill District - 15 min walk - 1.3 km
  • Hayden Homes Amphitheater - 15 min walk - 1.3 km
  • Deschutes Brewery - 15 min walk - 1.3 km

Getting around

  • Sunriver Station - 24 min drive
  • Redmond, OR (RDM-Robert's Field) - 24 min drive

Restaurants

  • ‪McMenamins Old St Francis School - ‬10 min walk
  • ‪French Bread Rack At Newport Market - ‬13 min walk
  • ‪Westside Tavern - ‬3 min walk
  • ‪Taco Salsa - ‬8 min walk
  • ‪Pizza Mondo - ‬10 min walk

Frequently asked questions

Is Historic Drake Cottage - Walk to Downtown Bend - Drake Park Across the Street - Perfect for Couples pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Historic Drake Cottage - Walk to Downtown Bend - Drake Park Across the Street - Perfect for Couples?

Check-in begins at 4:00 PM.

What time is check-out at Historic Drake Cottage - Walk to Downtown Bend - Drake Park Across the Street - Perfect for Couples?

Checkout is at 10:00 AM.

Where is Historic Drake Cottage - Walk to Downtown Bend - Drake Park Across the Street - Perfect for Couples located?

Located in Old Bend, this condo building is within a 15-minute walk of Drake Park and Old Mill District. Deschutes River and Des Chutes Historical Museum are also within 10 minutes.

Reviews

9.6

Exceptional

9.6/10

Cleanliness

6.0/10

Amenities

8.0/10

Property conditions & facilities

10/10

Check-in

9.6/10

Communication

10/10

Location

9.8/10

Listing accuracy
Rating 10 - Excellent. 69 out of 83 reviews
Rating 8 - Good. 8 out of 83 reviews
Rating 6 - Okay. 4 out of 83 reviews
Rating 4 - Poor. 1 out of 83 reviews
Rating 2 - Terrible. 1 out of 83 reviews

Reviews

10/10 Excellent

Diane M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Loved Drake Cottage and Drake Park!
Stayed 4 nights in Jun 2025

8/10 Good

Randy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

June '25

Drake Cottage 311 was very good for a weekend stay. Location excellent. Only small problem was a slow drain in one sink
Stayed 3 nights in Jun 2025

10/10 Excellent

Michelle F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location / Great space!

We had a great stay, the location was fantastic - walkable to everything and a beautiful view out of the front door. It was clean and comfortable and we would definitely stay here again!
Stayed 3 nights in May 2023

10/10 Excellent

Margaret Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Booked it again!!

Wonderful location!
Stayed 7 nights in Jun 2024

10/10 Excellent

Daniel S., Indian Rocks Beach

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect central spot for Bend OR, great host

Can't say enough, place was ideal for a couple. Central to everything, clean, comfy, all you'd want.
Stayed 5 nights in Jul 2023

10/10 Excellent

Kris M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place in a great location!

Super clean and very easy check-in/check-out. Great location with proximity to Drake Park. Due to the location, expect some level of car noise throughout the night, but it's a breeze to enjoy Old Bend while staying here. Overall a great place to stay.
Stayed 2 nights in Jul 2024

10/10 Excellent

Bonita K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect escape

A fantastic weekend in Bend! It was an easy walk to the shops and restaurants. Drake Park is stunning and the riverwalk trail is amazing. It was easy to pop home if we needed something- it was a cozy stay. Thanks!
Stayed 2 nights in Mar 2025

10/10 Excellent

Dennis D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location of this rental is perfect for being walkable to downtown, Old Mill, Galveston corridor...everything great about Bend actually. If you want monastery quiet, this isn't the place for you. It does sit on a busy road and you get the noise you would expect from a road central to all things great about Bend. The house tempered that noise enough that I had no problem sleeping. Everything was comfortable, and despite some communication problems surrounding some scheduled construction on the property that caused some minor parking headaches, that is an unusual circumstance and wouldn't stop me from staying here again.
Stayed 12 nights in Sep 2025

10/10 Excellent

Hannah S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute!

What a sweet little property. Perfect for access to Drake Park and fun restaurants nearby.
Stayed 2 nights in May 2024

10/10 Excellent

Tom B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Bend and Mt. Bachelor for a week

The property was perfect for 1 or 2 people. The separate and large sitting room was very comfortable. The bed was nice and bedroom had plenty of drawer space for clothes. The kitchen worked well for me as a cooked
Stayed 7 nights in Dec 2024

10/10 Excellent

Steve F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Place, Parking is a little difficult

The house is really nice, in a convenient location. It would have been nice to be informed about how to park before arrival.
Stayed 3 nights in Apr 2024

10/10 Excellent

Christopher C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

October at Drake Cottage

We were very happy with our stay at Drake Cottage. Although on a fairly busy street, the proximity to Drake Park, the river trail and downtown made it worth it. We were able to walk and ride our bikes to these places with ease, and having access to the storage shed was essential when we weren’t on our bikes.
Stayed 4 nights in Oct 2024

6/10 Okay

Anne Marie F.

Liked: Check-in, communication, location, listing accuracy

Bend

Location was fantastic! An easy walk to the shops, etc in Bend. A few issues with the accommodations which were addressed with the property management company.
Stayed 4 nights in Apr 2024

10/10 Excellent

Vincent M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pink Martini concert

Great little bungalow, clean and comfortable, albeit it's location makes hanging outside a little noisier than desired. Pleasant walk to old Bend along the river. We didn't use the kitchen much, but it was well-stocked. Comfortable bed and nice linens. Check-in/out was a breeze. We would rent again.
Stayed 3 nights in Aug 2023

10/10 Excellent

Kris D., Phoenix, AZ

Liked: Cleanliness, check-in, communication, location, listing accuracy

8 days in Bend

This was a great little spot for my husband and me to get to know Bend. We really enjoyed being close to Drake park and the water. Being able to walk to downtown was also perfect. The only drawback is that it is a bit noisy with traffic since the bedroom window is right on the street. But other than that we loved this place.
Stayed 8 nights in Jun 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

claire k.

311 Drake Cottage

Great spot! Close to downtown bend and right across from a beautiful park. Everything was in walking distance. Clean!

10/10 Excellent

John J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay.
Stayed 3 nights in Sep 2025

2/10 Terrible

Cynthia M.

Liked: Check-in, location
Disliked: Cleanliness, communication

Itrip management not responsive

Great location near park and town. Construction noise started early and was loud. . Comfortable living room. But other preventable issues. Missing and dirty linens! Had to send repeated requests for them. Then the items were delivered twice. The second one at 10:30 pm. Seems the property has a management company named iTrip. Very poor service
Stayed 2 nights in May 2025

10/10 Excellent

Jenna W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very sweet

Great location, and everything we needed!
Stayed 7 nights in Mar 2025

10/10 Excellent

Erik M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great choice for a stay in Bend

Great location. Easy and short walk to downtown Bend.Comfortable living room furniture. Bed frame was a bit rickety but mattress was comfortable. Some road noice from the street in front of the complex but not too intrusive. Small parking area on side might be a bit tight for larger vehicles.Overall a wonderful stay and would not hesitate to book again.
Stayed 4 nights in Jan 2025

6/10 Okay

Christine J.

Liked: Cleanliness, location, listing accuracy

Cute cottage

Exactly what I needed. Small cozy cottage on the river, walking distance to town.
Stayed 3 nights in Sep 2024

8/10 Good

Stacey D.

Liked: Cleanliness, check-in, communication

Cute and cozy but loud

This cottage was comfortable and cozy. However, the bedroom window faces a busy street and I could hear traffic easily. The first night they were paving/doing road work all night (would have been nice to know, I would have selected a different location as I was on a working trip.) The hot water is very slow to come in the bathroom sink. Parking was a nightmare - one night I had to park two block away, maybe there are more cottages than spaces. It was very clean and the furnishings were comfortable, and I really appreciated the iron and ironing board!
Stayed 4 nights in Sep 2024

10/10 Excellent

Michael S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Thank you for a clean and wonderful vacation!
Stayed 2 nights in Aug 2024

10/10 Excellent

Kayla J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Review

Parking was difficult with our truck and other quest parking inappropriately, otherwise we enjoyed our stay and loved the closeness to drake park for the river float
Stayed 2 nights in Jul 2024

10/10 Excellent

Nola M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful short stay!

The location of this property could not be better! Small sweet space that had everything we needed for two nights, nothing fancy, but the basics were covered. Would recommend this space others and would absolutely book again.
Stayed 2 nights in Jul 2024

About the host

Hosted by iTrip Vacations - Central Oregon

Host profile image

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback

Hotels

Holiday Rentals