The Quandary Vineyards Estate

7 BR
7 Baths
Sleeps 14
5,600 sq ft.

About

Welcome to The Quandary Estate—a truly one-of-a-kind private vineyard retreat in the heart of Oregon’s Willamette Valley. Set across 80+ acres of rolling vines, valley views, and open skies, this exclusive estate combines two stunning homes into one unforgettable experience—perfect for elevated group getaways, corporate retreats, celebrations, and wine country escapes.

Together, the estate offers 7 king suites, 7+ baths, multiple gathering spaces, and expansive indoor-outdoor living, all designed with intention, luxury, and connection in mind.

-Two Homes. One Incredible Estate.-

The Farmhouse – A single-level modern retreat featuring:

★ 3 king suites, each with private en suite bathrooms

★ Open-concept living with high-end finishes and a chef’s kitchen

★ Expansive deck with sweeping vineyard and sunset views

★ Heated/cooled garage lounge with ping pong and media space

The Gables – A spacious, multi-level luxury home offering:

★ 4 king suites with en suite baths and incredible valley views

★ Multiple living areas for gathering, relaxing, and entertaining

★ Massive elevated deck, firepit, and outdoor dining spaces

★ Game room, fireplace, and beautifully designed interiors throughout

Just a short walk apart, the homes create a private compound feel—ideal for groups who want to be together, yet still enjoy space and privacy.

-Designed for Connection & Experience-

This estate was built for moments that matter:

★ Morning coffee overlooking the vines

★ Long dinners with local wine and unforgettable sunsets

★ Fireside conversations under the stars

★ Friendly ping pong tournaments and relaxed evenings indoors

With multiple kitchens, dining areas, decks, patios, and living spaces, your group will always have room to gather—or spread out.

Sleeping Arrangements

Primary with En Suite: King
Primary with En Suite: King
Primary with En Suite: King
Primary with En Suite: King
Primary with En suite: King
with En Suite: King
with En Suite: King
Game Room: Sofa Full

Bathroom Configuration

Primary En Suite: Shower, Toilet, Tub
En Suite: Shower, Toilet, Tub
En Suite: Shower, Toilet
En Suite: Shower, Toilet
Half Bathroom: Toilet
Primary En Suite: Shower, Toilet
En Suite: Combo Tub Shower, Toilet
En Suite: Shower, Toilet
Half Bathroom: Toilet

Property Rules

Check In: After 4pm
Check Out: Before 10am
Smoking: Not Allowed

Amenities

Air Conditioning
Amazing Views
BBQ Grill
Balcony
Bathtub
Bird Watching
Body soap
Business Travel Ready
Cable
Carbon Monoxide Detector
Clothes Dryer
Clothing storage
Coffee Maker
Conditioner
Cooking Basics
Covered Patio
Dedicated Workspace
Desk
Desk Chair
Dining Table
Dishes And Silverware
Dishes Utensils
Dishwasher
Essentials
Family
Fire Extinguisher
Fireplace
Free Wifi
Hair Dryer
Hangers
Heating
Hot Water
Ice Maker
Initial paper products
Internet
Internet Access
Iron
Iron Board
Kitchen
Kitchen Island
Linens
Living Room
Long Term Stays Allowed
Microwave
Mini Refrigerator
Minimum Age Limit
Near Vineyard
Outdoor Furniture
Parking
Patio
Patio or Balcony
Ping pong table
Private Entrance
Refrigerator
Restaurants
Satellite or Cable
Self Check-In
Self Checkin Checkout
Shampoo
Shopping
Smoke Detector
Stereo
Stove
TV
Toaster
Towels
Vineyard Views
WIFI
Washing Machine
Wireless Internet
Bed

Map

Frequently Asked Questions

RULES AND REGULATIONS
1  Tenant agrees to leave the premises and its contents in the same condition, neat and tidy, as Tenant found the premises to be upon move-in, normal wear and tear expected. 
2  All dishes are to be washed and all garbage removed from the premises and placed in outside receptacles. 
3  No glitter or confetti is to be used or dispersed on the property. Failure to comply will result in extra cleaning fees of at least $300.00 at a minimum.
4  The maximum number of occupants shall not exceed the advertised number stated on the listing.
5  Furnishings are not to be removed from the premises for use outside or in other properties.
6  If Pets are allowed on Property a $100 per pet fee is required. Let us know if you will be bringing pets so we can send a $100 request per pet. Please pick up after your pets. If feces are left behind an extra charge of $50 applied clean up. If it is marked as "No pets" this policy must be observed and pets are not allowed on premises.
7  Smoking is not allowed in the unit. $500 fine if evidence of smoking is found in the unit.
8  Reservations are not made by or for a minor, defined as any person under the age of twenty-five (25).
9  Tenant and any guest of Tenant shall obey all laws of the state the rental vacation rental property resides in, as well as local laws, at all times while they are on the premises. Failure to abide by the laws of the state or the above rules may cause tenant to be asked to vacate the premises and forfeit all rents and security/damage deposits.
10  There shall be no noise that can be heard outside the home between the hours of 10pm - 7am. If noise is an issue, you will get a written warning text message to the number that booked the reservation and/or a phone call. If noise does not stop, you will be fined up to $300 or possibly evicted immediately.
11  Any items left that a guest leaves and wishes to be returned and shipped will incur a $30 fee plus shipping. 
12. Commercial use of the property, including filming, is prohibited unless approved with a signed location release form. Any unauthorized filming for commercial use will result in immediate eviction and possible legal action.

SLEEPING CAPACITY/DISTURBANCES
Tenant and all other 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 of the listings advertised guests, 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.

Violations of our noise rules or maximum number of guests agreed to at the time of booking will result in possible fines or immediate eviction with all loss of all rents.  Depending on severity if there is a noise situation we may call and issue a warning or proceed with a $300 fine. If we cannot reach the guest that booked the property someone will show up to at a minimum issue a $300 fine and/or evict the entire group immediately. Any delay will result in us involving the authorities and trespassing every person on the property as well as the loss of all rents. Additional fines or damages may be assessed after removal. 

HOLD HARMLESS
iTrip or the Owner, does not assume any liability for loss, damage or injury to persons or their personal property. Neither does owner accept any liability for any inconveniences, damage, loss or injury arising from any temporary defects or stoppage in supply of water, gas, cable service, electricity or plumbing, as well as due to weather conditions, natural disasters, acts of God, or other reasons beyond its control.
 
ADDITIONAL TERMS AND CONDITIONS
The undersigned Tenant, for himself/herself, his/her heirs, assignors, executors, and administrators, fully releases and discharges Owner from any and all liabilities, claims, demands, and causes of action by reason of any injury, loss of damage by whatever nature which has or have occurred, or may occur to the undersigned, or any of his/her guests as a result, or in connection with the occupancy of the premises and agrees to hold Owner free and harmless of any claim or suit arising there from. In any action concerning the rights, duties or liabilities of the parties to this agreement, their principals, agents, successors or assignees the prevailing party shall be entitled to recover any reasonable attorneys fees and costs. Owner reserves the right to terminate this Agreement upon their discretion at any time.

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Toll Free (833) 464-8747