Hill St Cottage 55

Romantic Stowaway. Walk Everywhere - Old Mill, Box Factory, Downtown. Quiet Bend neighborhood.

1 BR
1 Bath
Sleeps 3


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.

PLEASE inform us of your plans to bring your dog (no other pets allowed). One dog, less than 50 lbs only. Dog must be crated when left alone in unit. $75 pet fee for one dog applies. Owner must verify that dog is current on all vaccines and flea medications. Guest will pick up/clean up all pet waste and will be responsible for costs associated with remediation of fleas, or damage from dog. Dog not to be left unattended in property unless kenneled. Although we are pet-friendly please note your pet must not be left unattended at the house without you present, even if in a crate/kennel. Failure to adhere to the house rules as it pertains to pets may result in cancellation of the booking with no refund. **

Charming 1 BR standalone cottage 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

- Full-size foldout in living room


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

- Granite countertops

- custom dark wood cabinetry

- adjacent dining space

- French press coffee maker


- A/C

- Wall heating units

- Hardwood floors throughout

- Custom tile bathroom

- On site Shared Washer & Dryer (3PM-7PM)

- 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!

Creatively remodeled standalone cottage in Old Bend. Perfect for a couple with or without a youngster. 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.

Tastefully decorated bathroom, with custom tile and tub/shower combo.

Cozy sitting room with flat screen TV.

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, fire up the grill for dinner under the stars. (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.

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: 3 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.

Sleeping Arrangements

Bedroom #1 Queen
Living Area Sofa Full

Property Rules

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


BBQ Grill
Big Screen TV
Carbon monoxide detector
Clothes Dryer
Coffee Maker
Dining Table
Dishes Utensils
Dog Friendly
Enhanced Cleaning
Fire Extinguisher
Full Kitchen
Hair Dryer
Hot Water
Internet Access
Iron & Board
Iron and board
Linens Provided
Living Room
Open Patio
Parking available
Pets Considered
Private Entrance
Self Check-In
Shopping & relaxation
Smoke detector
Sojo Amenity Kit
Washing Machine
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.



Location location location
5/5 stars
The place was perfect. Location was within easy walking distance to downtown and Hayden Home Amphitheater. The cottage was clean and in a quiet neighborhood. We will definitely come back again.
- Chris
Great location
4/5 stars
Great place to stay. Small but perfect for a couple and very well equipped. Location is great and within walking distance to many popular districts in Bend. We have rented this property several times and have always been happy with it.
- Ryan
Pleasant surprise
5/5 stars
Was so lucky that the hosts accommodated a last minute reservation. And luckier to discover a cool spot. Next door to Boneyard tasting room and 5 minute walk to a restaurants and food carts. Walkable to downtown. The cottage was homey and clean. Kitchen has it all. The bathroom is huge and amazing. Locally roasted coffee waiting on the counter. I have a longer trip planned for Bend this summer and I will be back.
- Laurel
Great spot
5/5 stars
Great location! Really quiet location and just a couple minutes walk to the heart of downtown Bend. Very clean and well stocked, everything I needed for my stay. I didn't cook, but could of had there not been a great little Mexican restaurant one block over. Great communication from the host for check in and check out, they were really responsive. This was a quick trip for me for work, but if I come to Bend again, I would definitely stay here.
- Myles

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Contact Manager

Phone (503) 230-0534