Winners 38 - North Sunriver

4 bdrm, Quiet Location w/ Amazing Wrap Around Deck For Grilling Out


House : 2 Floors

Up to 10 guests

Bedrooms: 4 / sleeps 10

Bathrooms: 2.5

Sq Ft: 1900

Pet Friendly (Dogs only - 2 max)

No Smoking


  • Free Wi-Fi (100 mbps)
  • King Bed(s)
  • No Sharc Passes (See Bennington Guest Perks)


Cal King Primary Bedroom upstairs

1 King Bed

Queen Bedroom downstairs

1 Queen Bed

Queen Bedroom downstairs

1 Queen Bed

2 Bunkbeds Bedroom downstairs

2 Bunk Beds

House Rules


38 Winners, Sunriver, OR 97707


Welcome to 38 Winners Circle!

- 4 Bedrooms, 2.5 Bathrooms, Sleeps 10
- Air Conditioning, Gas Fireplace
- Private Hot Tub
- Dog Friendly
- Free High Speed WiFi (300 mbps)
- Ping Pong

Great home in north Sunriver with tons of gorgeous natural light pouring in through the many windows. This reverse living , air-conditioned home features a great room upstairs with cozy living room furnishings, dining room with seating for 8, plus 3 more at the breakfast bar and a fully stocked kitchen with a Keurig.

Upstairs you'll find the king primary bedroom with large TV, sitting area, private bath with walk-in shower plus a half guest bathroom.

Head downstairs to find 2 queen bedrooms and a bunk room with 2 sets of bunks, TV and DVD plater.

Head outside to enjoy a private hot tub, and a large wrap-around deck to enjoy dining al fresco or soaking up that wonderful Sunriver sunshine. Nearby bike pathways provide easy access to the north grocery store and Woodlands golf course.

There is ping pong in the garage so you can enjoy a friendly game with friends or family. Take a bike ride on one of the 3 adult bikes provided with this vacation rental house, Deschutes river access is a short ride from this home, or for a more ambitious ride, head north 5 miles to Benham Falls.

This home welcomes dogs, 2 max, no other pets are allowed. Fees apply


Cooking Stove
Coffee Maker
Dishware & Cookware
Keurig - Bring your own K-Cups

Adult Bikes
Ping Pong Table
Cable TV

Hair Dryer
Gas Fireplace
Shower/Tub Combo

Outdoor Grill Gas
Large Deck
Enclosed Deck

Standard Amenities
Coffee maker
Coffee Bean Grinder
Upright Blender
Bottle Opener & Corkscrew
Can Opener
Knife Set
Knife Sharpener
2+ Kitchen Tongs
2+ Cooking Spatulas
Large Spoons (solid & slotted)
Storage containers with lids (glass preferred)
Vegetable Peeler
Measuring Spoons (full set)
Measuring Cups (full set)
Cheese Grater
2+ Cutting Boards (dishwasher safe, not wood)
3+ Frying Pans (assorted sizes) .
3+ Saucepans (assorted sizes w/lids)
Large Pasta Pot
Roasting Pan
Cookie Sheets
Casserole Dishes (lids preferred)
2+ Mixing Bowls
BBQ Cooking Utensils
Dinner Plates
Salad/Dessert Plates
Coffee Mugs
Drinking Glasses (small and large tumblers)
Wine Glasses
Steak Knives
Plastic Cups (for children)
2+ Serving Bowls
2+ Serving Platters
Utensil Set
Step Ladder
Iron and ironing board
At least one hair dryer


(26 reviews)

Winners Circle winner

Katherine - Forest Grove


Great place to stay with a dog. Large deck with gate was a plus and allowed our two dogs to spend a lot of time outside with us. Yard very private and peaceful. Indoors, lots of windows to view the scenery.

Nice and quiet place

Erick - Camas


Nice and quiet place.

Love staying in this area of Sunriver

Pam - Portland


Small thing but really loved the cabinet with pulled out empty bins. Most places don’t have a space for all the food we bring.

38 winners circle

Lisa - Coos Bay


We loved the location. Nice loopwith nice houses

STEPHEN - shelton


Winner's Circle

Anne - Medford


Floor plan works well for dogs as the upper deck is completely fenced and locked off. Dogs could be outside and locked in.

Great stay at a great house

Jenae - Wood Village


This is a great place to stay with a large family. The master bedroom was fantastic. It was very roomy and the bathroom and shower were great. The other three bedrooms downstairs while small were very nice. We loved the kitchen and dining area and spent most of our time there playing games and eating. The hot tub was amazing too! We loved our stay.

Brittney - Dundee


Ted - Bend


Good location!

Stephanie - Tualatin


It was easy to work with Bennington Properties and they responded immediately to all concerns and requests. Kitchen very well stocked. House was clean. Good location. Quiet in early to mid-May. Bicycles available. Hot tub available; although we never used it. ;-/

Had a great stay!

Julia -


Had a great stay. loved the big space of the kitchen and common area (very comfortable). Would Stay again.”

38 Winners-great stay

Katy - Walnut Creek


Great location, nice and quiet Great layout Nice hot tub Easy access walking trails Liked the bikes and ping pong

Enjoyed 38 winners!

Jennifer - Coos Bay


It worked great for multiple families. It sleeps 10+ comfortably. It had nice extras and a good bbq. We enjoyed ourselves!

Family get together

Alice - Eugene


The layout of the home is great for several people. The neighborhood was quiet, we enjoyed ourselves

Great for 8

Molly - Tigard


We were a party of 8 (two families), and the house was plenty spacious for us. The wrap-around deck is great. It would be nice to have seating outside for 8-10 so we could have all eaten together on the deck. All in all, a great house rental.

It was a great stay!

Kimberly - Redmond


This was a beautiful home and was very clean and comfortable. It had a lot more kitchen items than expected so filled all my cooking needs. The deck is beautiful, hot tub was awesome. Boys enjoyed the ping pong table. We just did not give ourselves enough time to enjoy everything! We definitely want to rent this house again next year!

38 Winners

Jessica - Beaverton


Great layout and very cozy! Pots and pans are quite old / chipped. I would pack my own if I went back. Other than that, we loved it!

Hi Jessica, thank you for choosing Bennington Properties and taking the time to share your feedback, we appreciate it. I'm sorry to hear that the pots and pans were not up to par. I am going to look into it and make sure that the home is stocked up to our standards. I'm glad to hear that you enjoyed your stay regardless, and we hope to see you again soon! - Sam

Thank you! 2018-12-11

38 Winner Circle-- Good for big families

Alicia - Corvallis


38 Winners Circle was a nice place for my family to stay. There were 8 of us, 6 adults and 2 kids. We were very comfortable. There was plenty of space to spread out and the three TV's allowed people to catch up on News and Sports, without disturbing the family dynamic. The kitchen was well equipped, very well stocked with dishes, glasses, and tools. It allowed us to make food during our stay. The beds were soft but comfortable, but the pillows were too big and firm for my taste. The house stayed warm (we were there on a chilly fall weekend), but the heater ran every 90 minutes for about 10 minutes all night long. We left the gas fireplace on upstairs all night and reduced the need for the furnace to run, keeping the downstairs bedrooms cooler (my family likes to sleep cool).

Great Family Gathering

Jessica - Jacksonville


We had 3 families staying at 38 Winners Circle and we all had an amazing time. The location is ideal at the north end of Sunriver, where things are just a little quieter and more relaxing.

Winners 38 is a Winner

Patrick R. - Halsey


Our stay in 38 Winners was pleasant as usual. The property was very clean and well maintained. Kitchen/cooking facilities were well suited to our family's needs. There isn't much parking, 3 cars were very crowded, but it works. The bunk beds are not very comfortable for taller guests.

Hi Patrick, Thank your for your winning review of our 38 Winners Circle home. We are so glad to hear that another stay with us was so great and that the kitchen was stocked well for your family. We appreciate your continued business and we hope to have the pleasure to host you again in the future. -Jess Rae

Thank You 2016-03-02

Most enjoyable retreats through Bennington Properties

Pat H. - Bend


This year we rented four homes from you for our annual Women's Retreat and always enjoy our stay. Each house hostess said all guests in their homes were more than comfortable and that your information packets were very helpful. I have in the past and will continue going through your friendly, helpful, and professional group. Thanks for a great time.

Hi Pat We are so happy to hear everyone enjoyed the homes and Retreat. Can't wait till we see you again next year Bennington Properties

Response from Bennington Properties, LLC 2015-12-03

Very Lived In But Comfy

Susan K. - Vancouver


Let's start with the bad and get it over with: The house is a bit "sticky". Kitchen cupboards have a layer of stuff on them that is nasty to the touch and cannot be removed (we had housekeeping come out and try to no avail). Living room furniture is fairly worn out, you sink way in once you sit down and one chair broken so it's unusable. There is a strong dog odor from entry way into the downstairs (we do understand that pet friendly homes sometimes smell like pets but you should be forewarned). We didn't notice it upstairs at all but it was pungent upon entering the house. The windows were not clean. Once the sun shone through in the morning they showed a LOT of dirt and grease.Housekeeping came out and cleaned the lower ones but the upper ones remained dirty for the stay. This is a bummer if you like to look out and enjoy the beautiful surroundings. <br/> Now the good: This is a very livable home. The kitchen is wonderfully laid out and easy to maneuver several people in at once. The beds were all comfy. The master especially nice and HUGE. Bathrooms upstairs really nice, downstairs just okay, dated. By FAR the best part of this home is the deck! We lived out there every evening. It is huge and there is lots of comfy patio furniture. The bikes, hot tub and ping pong table all were in great shape and worked fine. We all liked the privacy of the location. All in all, if they do a couple of easy fixes, we would come back.

Hello Susan, Thank you so much for your feedback. I am sorry the house was in the shape it was in when you arrived. I will be passing these notes on to the owners and work with them to see what we can do. I am happy to hear that you were able to enjoy your time here and that the patio was comfy for your family! It's nice to be able to spend time outside during the summer months. We appreciate your business and we hope to see you again in the future. Sincerely, Kassie - The Guest Services Team.

Response from Bennington Properties, LLC 2015-10-29

Needs some updating

Gary B. -


Overall the house was nice. Furniture a little old but functional except for one chair that had something wrong with then swivel base. Kitchen cabinets where you grab to open and close need some heavy cleaning because they feel sticky to the touch. Floor plan is very functional. Hot tub layout is nice. Bedding and towels are good.

Thank you for your feedback Gary. We have addressed the swivel chair and also the kitchen cabinets, so thank you for the heads up on that. We hope to see you again soon! Christina Guest Services Manager

Response from Bennington Properties, LLC 2015-12-29

Quiet retreat

- North Platte


We stayed at the north end and loved the seclusion. It was only minutes to the village. Our house was very clean and well stocked . We were a party of two families one with a small child and dog. We enjoyed the 4 bikes but wished there would have been one with a child carrier. The only con I had about home was that it could use some updating . The office of Bennington properties were so helpful and nice .

Lisa, Thank you for your feedback, I am happy to hear that the location of the property and cleanliness worked well for you. I will pass along your suggestion of updates to the owners and thank you again for bringing the whole family to beautiful Sunriver for a week. We hope to see you again next year. Best Regards, Misty Wagner Guest Services Team.

Response from Bennington Properties, LLC 2016-01-12

Winners Circle #38

Aaron A. - Portland


It was great! Really nice house with nice cooking supplies, decor, layout, etc. Bikes worked great, ping-pong was fun, and the hot tub was hot. We had a great time and will likely rent that house again!

Thanks Aaron! We are so glad that you enjoyed your stay and we look forward to seeing you next time! Christina Guest Services Coordinator

Response from Bennington Properties, LLC 2015-04-28

It's A Winner

Jerry G. - Portland


We had a great stay. The rental was clean and well prepared for our visit. The renters seemed to have already thought of everything.

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