Trailhead Property Management - Bend and Central Oregon Property Management
Trailhead Vacation Rentals

Featured Listings
River View Contemporary Townhouse

This is a contemporary 1,740 sq. foot townhouse with hardwood floors and floor-to-ceiling windows over-looking a canyon with the Deschutes River. The home includes: “open concept” large fully-equipped gourmet kitchen / living room, dining area, fireplace, master suite, second guest bedroom and bathroom and full laundry room with state-of-the-art washer / dryer. There are flat screen tv’s in both bedrooms, living room and kitchen. There is a deck off the master, plus a larger deck with a gas bar-b-q and patio furniture accessed from the dining area. To secure sports equipment, there is a locked storage closet adjacent to the from door. This townhouse is easily accessible to the River Trail, a walking / running path along the Deschutes. - Outside amenities on Mt. Bachelor Village property include tennis courts, swimming pool (March – October), and year-around hot tub. 


BRAND NEW River Camp Home

Beautiful, family friendly, 2 story brand new house. Both bedrooms have queen beds with full sized pull out couch in the living room. A/C, outdoor area, stainless appliances, washer and dryer, garage storage. Fully stocked for all your vacation needs. Minutes to the river, close the mountain, and bike-able to downtown or the Old Mill.

(Pets accepted with pre-approval from owner and additional refundable deposit)


West Side Beauty!
Can't Get Much Closer to Mt Bachelor and Cascade Lakes Hwy

Welcome to Elder Ridge, a newer luxury home in Bend's West Side. Close to downtown and the Old Mill District, yet with easy access to Mt Bachelor, a short walk to the Deschutes River Trail, or a short ride to mountain biking on Phil’s Trails. Boasting a fabulous architectural layout, this home has an open floor plan with high ceilings, 2nd floor balcony, contemporary furnishings, and lots of windows throughout. Gorgeous light hardwood floors accent the dining and kitchen areas. An absolutely stunning natural rock enclave frames the backyard for private dining and soaking in the hot tub. This home is ideal for 2 families, an extended family get together or 3 couples. 

This is a new vacation rental and has all new furniture and furnishings. A lovely Queen Master Suite with private bath graces the first floor. The upstairs King Master Suite has it's own balcony entry, private bath and door to the backyard hot tub. A second Queen and Twin Bunk complete the third and fourth bedrooms. The second full bathroom has a deep soaking tub.

The open floor plan seamlessly melds the living, kitchen and dining room areas. High vaulted ceilings and large windows create a light, spacious sanctuary of beauty and comfort. The gorgeous gourmet kitchen is fully stocked and beautifully appointed. The dining room table easily sits eight

Enjoy outdoor grilling and soaking under the stars in the private natural rock walled back yard. Simply beautiful.


3br - 1521ft - Gorgeous west side furnished m-to-m rental

This newly renovated home is on Bend's desired west side and includes the best amenities for a relaxing adventure vacation in Oregon's top tourist destination. Two bedrooms and one bunk room, 2 bathrooms, and spacious great room. Attached two car garage. This home includes a BBQ and putting green in the back yard. It is all furnished and ready to help you entertain and make the best of your time spent in Central Oregon. Also an ideal transition home for those building and needing a place to crash until your dream home is done!


We are now offering vacation rental management services:
* Advertising
* Guest booking
* Housecleaning
* Bill pay on rental property
* State and county room tax payment
* Maintenance issues

In addition to all the traditional vacation rental management services, of special note are our guest concierge services.  Our goal with this is to provide a level of service that creates loyal customers such that repeat business is commonplace with our properties. 

Included in all room rates are:

* Arranging tee times or other recreational activities (rafting, etc.)
* Making dinner reservations
* Booking bike or ski rentals and delivering the equipment
* Grocery store and/or Costco runs to stock the refrigerator pre-arrival (guest will pay for the cost of the groceries)
* Restaurant recommendations

At an additional cost to the guest we will also provide the following services if requested:

* Party planning
* Daily cleaning
* Nightly turn-down service
* Take-out delivery
* Other specifically requested services

Call us today to see how we can turn your vacation rental into the investment property you dreamed it could be.
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