We are local iin Sunrver You Will Appreciate The Difference - Sunriver Vacation Rentals Sunriver Vacation Rentals - Coffee Appreciate The Difference

Sunriver Vacation Rental Management


WELCOME TO BENNINGTON! We are so glad you chose Sunriver as the location for your second home. We have a team of Owner Services and maintenance associates standing by to assist you.  Our team is available 7 days a week to assist you and 24 hours a day for emergencies. Please stop by our office to meet our team of professionals.  Enjoy a complimentary drink while you relax by the fireplace in our living room.

Got questions?  Contact us by any of the channels below.

Call us at 800.313.5242
Text us at 541.705.2267
Email us

The Bennington Difference


Protect your investment

You have worked hard to own a second home.  You need, and deserve, to have the best company watching after and protecting your investment. 


Exceptional Communication

You want it and we will deliver it.  Timely and in the method you like.  Oh, and we live right down the street from your Sunriver property.

Highest Possible Income

We will deliver to you the highest level of income possible for a house of your quality and size.



Partnership & relationship

All decisions made with a focus on creating a strong relationship of mutual respect, trust, and success.


Management Fees

We charge a commission only; no hidden fees, no nickel-and-diming; we don't get paid until you do. Our commission is determined based on the needs and goals of the property owner.  Lower commissions WITH fees available as well.

Services We Provide

Bennington Properties is a full service vacation rental management company; handling all of the details for your home. The following is a snapshot of the services included with our commission:

•  Professional photography, no limit to # of photos
•  Marketing and reservations (including listings on Benningtonproperties.com, Sunriver Blog, VRBO, Airbnb, Facebook, Instagram Google Adwords, etc.)
•  10% commission savings on homeowner-referred reservations
•  Dedicated and local 24-7 reservation team that KNOWS your home
•  We pay all credit card fees
•  We pay all state and county lodging taxes
•  Financial assistance to upgrade your home
•  24-7, year-round care
•  Basic and preventative maintenance - All labor associated with our maintenance is complimentary and we will only charge for the cost of an item itself, ie: specialty light bulbs.
•  Property Inspections
•  Guest supplies (ie: toilet paper, soap, paper towels, sponge, trash bags)
•  Housekeeping and linens - We provide fitted/flat sheets, pillow protectors & cases, bath, hand, and kitchen towels, as well as standard bath mats.
•  Smart home security
•  24-7 temperature management and monitoring
•  Up to two seasonal deep cleans
•  Guest Damage Guarantee
•  Housekeeping Guarantee
•  Discounted SHARC & Marina for summer guests
•  Complimentary tennis and pickle-ball court access for guests
•  Complimentary Sage Springs Fitness passes for guests
•  No FEES for owner or owner guest stays
•  Discounted owner cleaning fees
•  Year end 1099 tax filing and full expense reports
•  No restrictions on owner stays
•  Company owners that live right down the street from your home and that are available to you 7 days a week

Additional Services

Summer ONLY rentals and year round security inspections available as well.

Start Up Costs

Bennington Properties has no start-up costs (with the exception of any kitchen, safety, or other supplies you might purchase at wholesale cost from Bennington Properties).

Joining is EASY!

We make joining our program EASY!  Whether you are a first time vacation rental owner or looking to switch from another management program, we make joining EASY.   We will get your home up and rocking and rolling as quickly or as slowly as you want.

•  A thoughtful and flexible agreement
•  No start-up costs
•  No SHARC expense
•  One-on-one consulting to make your property a successful vacation rental
•  Every member of our Sales Team previews your property
•  Complimentary deep clean
•  Professional photography
•  Unlimited webpage updates
•  A full inventory of your property
•  A full maintenance inspection
•  A full safety inspection

What marketing will you do for my home?

The goal of marketing in the vacation rental industry is to produce a large number of people interested in staying at your home (leads).  In Sunriver, Google is the number one source for vacation rental leads.  Bing, Yahoo, Airbnb.com, and VRBO.com are distant seconds.  We market effectively and extensively on these websites and more.  Our Sales Team generates leads by continually marketing, by phone and email, relevant and personalized information to people interested in Sunriver.  If someone is interested in staying in your home we will continue to follow up with them until they book.  No lead left behind!  Bennington Properties is leading the industry in converting leads into reservations using four unique ways; reputation, relationship-focused sales, web presence and technology.

Reputation.  Bennington Properties has effectively, since our start in 1998, taken great care of our guests.  This care has translated into a strong reputation of service excellence resulting in the highest percentage of return guests in the industry.

Relationship-Focused Sales.  By focusing on getting to know the guest and their individual needs our team is able to build relationships of loyalty and trust that has resulted in one of the highest lead conversion rates in the industry.

Web Presence.  Using the same philosophy and model that has made Amazon.com a success, we are continually improving and enhancing our website with the latest web technology resulting in a higher than industry average online booking rate.

Technology.  We use multiple forms of technology to market to guests. For email marketing we use a web based platform called REACH (Real-Time CRM Data Marketing System) that sends the right message to our clients at the right time to drive direct demand and increase revenue. Our Bennington smartphone App has become very popular among our guests and allows us to stay in contact before, during, and after their stay. Through the app we can let our clients know of special offers, promotions, and to encourage them to re-book your home for their next Sunriver vacation.

What type of expenses can I expect?

The following estimates are based on the ANNUAL expenses for properties in Sunriver.

SROA Fees
(depends on SHARC assessment)
$1600
Sunriver Water $900
Hot Tub Service
(through a local hot tub service provider)
$1400
Garbage $400
Cascade Natural Gas $700
Midstate Electric
(depends if electric only)
$1500
Ongoing Maintenance
(Misc supplies, vendors, etc.)
$3000
Snow Plowing
(depends on season - based on an average of 8 plows)
$440
Total Expenses: $9940

What gross rent can I expect?

Gross rent for a vacation rental depends on many factors including amount of owner use, location, amenities, age, online reviews, appearance, and more.  We have included an average gross rent for each property and the range of rent that the properties make within that category.

  Average Range
1 Bedroom $20,409 $14,931 - $28,206
2 Bedroom $25,494 $14,188 - $40,831
3 Bedroom $24,943 $15,107 - $36,912
4 Bedroom $32,928 $24,038 - $67,779
5 Bedroom $43,457 $34,213 - $58,922
6 Bedroom $83,012 $57,647 - $116,554

Contact Us With Your Questions

Contact us to confirm why partnering with Bennington Properties is the BEST CHOICE for your Sunriver / Caldera Springs investment.


Jessica Pritchard ♦ Shannon Gleasman 

Owner Services Manager ♦ Sales Manager & Broker
Email ♦ Jessica (541.594.0407) ♦ Shannon (541.326.2184)
Learn more about Jessica ♦ Learn more about Shannon 


Robert W. Bennington

CEO, Owner
Email ♦ Call or text (541.948.0214)
Learn more about Robert 

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