Family-friendly holiday rentals in Willamette Valley

Luxury Wine Country Estate

Welcome to Luxury Wine Country Estate, an oasis where luxurious refinement meets the epitome of wine country indulgence. Revel in unmatched hositality, thoughtfully designed to include Tempur-Pedic suites, therapeutic hot tub, rejuvenating sauna, invigorating cold plunge, and the most stunning valley and vineyard views. Every touch is meticulously crafted, from heated stone floors and Dyson innovations to dual gourmet kitchens, Yeti picnic essentials, EV charging capabilities, and so much more.

Gorgeous Mt. Hood View, Ski, Hike or Mt.Bike

Welcome to Sandy Oregon, the Gateway to Mount Hood. This Luxurious cabin-feel home, custom built by top notch craftsman and designer, features breathtaking panoramic views of Mt. Hood and the Sandy River. The view is rated one of the best in the Northwest. Enjoy a glass of wine while sitting by the outdoor fire pit, take a short drive to Timberline Lodge for skiing or snowmobiling, go hiking in the Mt. Hood forest or Mountain Biking at world class "Sandy Ridge". Your options are unlimited!

Vineyard and Mountain View Wine Country Retreat

Our property is available to adults looking for some peaceful time. Conveniently located, our home will be a retreat to come back to after a day of exploring gastronomy and wineries in nearby towns. Numerous vineyards are in the immediate vicinity. On clear days enjoy views from our large deck of Mt Hood, St Helens, Rainier, and local vinery. We take great pride in maintaining a quality environment to share with others. Carefully read Additional Rules to decide if our home fits your needs.

Figment Farmhouse

Enjoy this charming 1950's farmhouse, situated on 150 acres of countryside. Within an easy drive of Carlton, McMinnville, and Dundee—it's an ideal location for the exploring the area's many offerings. The house is well-appointed and surrounded by abundant gardens, towering cedar and fir trees—plus, a flock of chickens, three heritage sheep, and our Bengal cats add interest to the place. We live on the property (next door) with ample privacy/gardens between our place and the farmhouse.

RiverLoft On Roaring River 20 miles to Albany

CRAVING TRANQUILITY? Find Your Escape and Forget the hustle and bustle and UNWIND AT RIVERLOFT! This is a two level Timber Frame structure. The kitchen area is downstairs. The living area, dining, bathroom, and sleeping areas are upstairs and are an open loft. This property is on a dead end road surrounded by privately owned timber tree farm. It has river frontage along the the Roaring River. It has a private picnic area along the river to enjoy the sun and shade during the day.

Luxury Wine Country Suite at the Market Lofts

Steps away from world class tasting rooms & directly above local hotspot, Red Hills Market, our loft is located in the center of it all. Decorated with a blend of rustic wine country style and industrial modern elements, our one-bedroom suite includes a separate living area with a sleeper sofa. Measuring 600+ square feet, it is perfectly sized for 2-4 people. Residing above Red Hills Market adds to the appeal & offers endless opportunities for fun...,wood fired pizza, wine & more!

The Historic Dayton Wine House

Stay in one of the top rated vacation rentals located in the heart of the Willamette Valley wine country. This majestic 1885 Victorian style home sits prominently on the charming town square of Dayton, Oregon, 30 miles from Portland, a perfect location for winery exploring! The beds and linens are of high quality for a great nights sleep. The small details are not forgotten in this large home with plenty of room for everyone to spread out.

Chef’s Kitchen + Firepit | Midcentury Wine Stay

★★★★★ “Amazing kitchen, great backyard, and fantastic location.” Welcome to your midcentury wine country escape—a designer home in the heart of McMinnville. After a day of tastings in the Willamette Valley, cook in the chef’s kitchen, sip Pinot under bistro lights, and gather by the firepit beneath the stars. This home is more than a stay—it’s a tribute to Oregon’s pioneering winemakers and the relaxed, joyful spirit of the Valley.

Fern Creek Farm Retreat

Fern Creek is a small family farm nestled in the forested hills of Yamhill County's wine country. Guests enter a captivating peace-filled space (a separate apartment in the lower level of our home), which is surrounded by forests and gardens where all kinds of life flourishes. Our sustainability practices (see below) demonstrate our commitment to helping life flourish--at Fern Creek and beyond.