Hill St Cottage 334

Old Bend 2 Bdrm Duplex, walk to Box Factory, Old Mill, brew pubs, wine tasting. Near Downtown.

2 BR
1 Bath
Sleeps 4


You can’t find a better place than Central Oregon to escape the stress safely. River, hill, and trail welcome you and promise to help you rejuvenate.

We clean our properties in compliance with the guidance prescribed by the CDC, and we provide hand sanitizer, disinfectant spray, and wipes.

Charming 2 BR unit in quiet Old Bend neighborhood. Walk to Box Factory, and Old Mill. Easy bike ride through all of the historical Bend neighborhoods.


- BR #1: Queen Size Bed, end tables, reading lamps

- BR #2: Queen Size Bed


- Stainless steel appliances, including full-size refrigerator-freezer, 4 burner stove and oven, dishwasher, microwave, and toaster

- modern countertops

- vaulted ceiling

- custom dark wood cabinetry

- adjacent dining space

- French press coffee maker


- A/C

- Wall heating units

- Tall dining table for 4

- Peninsula seating

- Vaulted ceilings in Bedroom #1

- Hardwood floors throughout

- Shared Washer and Dryer

- Hair dryer

- Iron and ironing board

- Wi-fi

- Parking


- Hiking

- Biking

- Skiing, snowboarding

- Sledding

- Snowmobiling

- Paddle Boarding

- Tennis

- Kayaking

- Golf

- Canoeing

- Floating/Tubing

- Wave-riding

- Bird Watching

- Fishing

- Ale Trail

- Shopping

- Dining

- Cascade Lakes Byway

- Concerts

- Brewery Tours and Tasting

- Wine Tasting

- and More!

Stylishly updated 2 BR duplex in Old Bend, perfect for two couples or small family ready to explore Bend. Summer guests will be drawn to all of the walkable river and trail attractions in town. Shopping, brew pubs, wine tasting, coffee, and bakeries are leisurely strolls from your front door. Slope lovers are just blocks away from Colorado Ave, which whisks them away to Mt Bachelor.

Bedrooms have separate entrances to the custom-tiled bathroom, with tub/shower combo.

The open floor plan blends the kitchen, with its peninsula and bar stools, to the living room with its over-sized sofa and chair.

River trails are a 5 minute bike ride away. The walkable destinations are endless - Foxwood Bakery, Immersion Brewing, Spoken Moto, Bledsoe Family Winery, Podski food truck court, Market of Choice, and everything Box Factory and Old Mill. Esta Bien and Boneyard Brewing tasting room are steps away.

Dine outside on the private deck, burgers fresh off the grill. (shared grill in common area)

Please note: Reservations made with less than 48 hours notice will require photo ID and credit card validation.

NO SMOKING allowed at this property.

NO PETS allowed at this property.

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 special retreat in Bend. The Good Neighbor Guidelines are in the binder.

Maximum Occupancy: 4 Occupants - Children must be counted within the maximum occupancy unless they are under the age of two (2) 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.

We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Winter activities include admission to Juniper Swim and Fitness, Mountain Air, and XC ski/snowshoe rental. In the summer, enjoy Juniper Fitness and Mountain Air, along with bike and tube rentals. Create exciting memories, have more fun, and truly experience your destination!


Activity program not valid on stays over 28 days.

334 NW Hill St Bend, OR 97703

Sleeping Arrangements

Bedroom #1 Queen
Bedroom #2 Queen

Property Rules

Check In: After 4pm
Check Out: Before 11am
Smoking: Not Allowed


Air Conditioning
BBQ Grill
Big Screen TV
Clothes Dryer
Coffee Maker
Enhanced Cleaning
Fire Extinguisher
Full Kitchen
Hair Dryer
Internet Access
Iron & Board
Iron and Board
Linens Provided
Open Patio
Parking available
Private Entrance
Shopping & relaxation
Washing Machine
carbon monoxide detector
iron and board
smoke detector
Bed linens provided
Gear Shop
Mountain Climbing
Rock Climbing
Winery/brewery tours
Gift Shop
Jewelry Store
Movie Theater
Rock/mountain climbing
Shopping Mall



Frequently Asked Questions

No open flames are permitted on balconies or in the unit. Do not dismantle smoke detectors. Use the overhead stove fan when cooking.

Reservations made for teenagers or young single requires an accompanying adult staying in the unit at ALL times. At least one member of the party needs to be 25 (twenty-five) years of age! Any violators will be evicted according to Oregon law with forfeiture of all monies.

Any reservation obtained under false pretense will be subject to forfeiture of reservation deposit, damage deposit, and/or balance of rental payment.

No daily maid service.  Additional cleaning fees will be due in the event that cleaning involves the removal of excessive debris, excessive spillage or staining of carpets, or uncleaned cooking grease and stains.

We reserve the right to charge guests for not complying with house cleaning rules.  Specifically, we reserve the right to charge guests if all dishes have not been cleaned either in the dishwasher or by hand, if all trash is not bagged and cinched, and if all perishable food has not been disposed.  

No compensation will be given for temporary outage of electricity, gas, water, cable, or internet. Outages will be reported immediately and all efforts will be made to have them restored as soon as possible. 

If security cameras for outdoor visual monitoring are present at the property, the listing will disclose this fact.  Tenant accepts the monitoring of the outside and agrees to not tamper with the security system.
Smoking is strictly prohibited in the property AND on premises. Any evidence of smoking will result in $150 fine, plus the cost of smoke remediation.

If you are staying in a dog-friendly property and are planning to bring your dog, you must notify us.  No more than one dog is allowed unless prior arrangements have been made.  A dog fee is required, and it varies depending on the property.  You must confirm your dog is flea and tick free, and is up to date on all vaccinations.  Dogs are not allowed on the furniture or bedding.  Please notify us of any accidents that occur in the home.  Please clean up outdoors.

If you are staying in a No Pet property, we reserve the right to take any or all of the following actions if a pet or Emotional Support Animal is brought onto the property,  a) charge a pet fee, b) charge extra for cleaning or picking up behind the pet, c) charge a fee for neighbor complaints, d) charge a refundable damage deposit, e) ask tenant to vacate the premises with no refund of any fees or damage deposits paid.

All occupants will be required to vacate the premises and forfeit the rental fee and security deposit for any of the following: Occupancy exceeding the sleeping capacity, people using the premises for any illegal activity, causing damage to the premises rented or to any of the neighboring properties and any other acts which interferes with neighbors' right to quiet enjoyment of their premises.

Packages delivered by UPS and FedEX ONLY.

iTrip or the Owner are in no way responsible for bodily harm or injuries that may occur while using the bicycles provided by the property. The Guest agrees to use the bicycles at your own risk. You are responsible for wearing helmets, and for securing the bikes. The Guest is responsible for the bicycles should they be lost or stolen when not on the vacation home premises.

Please report any maintenance needs for the premises to the us and we will respond as quickly as possible. Refunds will not be made for maintenance issues including, but not limited to heating and air conditioning, appliances, televisions, and sound equipment.

The owners furnish linens and towels. Lost or damaged linens may be deducted from your deposit. An initial supply of products is provided. Extra items needed are the responsibility of the Tenant. Limited cleaning supplies may be provided. We recommend that you bring any special items that you may need.



Perfect Getaway!
5/5 stars
Perfect getaway! I had the perfect getaway at this lovely cottage in Historic Bend. It had everything I needed and more, and was such a beautiful, quiet space, especially with the vaulted ceiling and open kitchen/living area. It is a perfect walking/biking distance through peaceful Old Bend neighborhoods to all of the great places to explore and enjoy in Bend -- Downtown, Drake Park, Deschutes River Trail, Old Mill, the Box Factory, restaurants, and more renowned breweries and tasting rooms than you could visit in a week. Plus, all the mountain adventures are just a quick trip up Cascade Lakes Highway, which is very easy to access from here. This lovely cottage truly was the perfect location and served all my getaway needs. I will definitely be going back!
- Monica
Perfect location, cute little home!
5/5 stars
My boyfriend and I came down for a 3 night stay Friday-Monday. The home was easy to locate, immaculately clean, had plenty of towels and amenities, and the most comfortable bed and pillows! It was a 2 bedroom with plenty more sleeping room but we wanted a weekend away just us. We went hiking, visited family in Redmond, shopping, dined and drank and the local breweries. Packed a lot into our little get away! Quite area, super cute yard, we had the most fulfilling and wonderful weekend we’ve ever had together. We will definitely be coming back to recreate our stay!
- Ashley Myers

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Contact Manager

Phone (541) 497-8041