Family-friendly vacation rentals in Dundee

5.0 out of 5 average rating, 209 reviews

A spacious family room is seen, featuring a mix of comfortable seating options, including a gray sectional and a light-colored armchair. A large dining table with cross-back chairs is positioned near the windows. Decorative elements include a rustic shelf and wall-mounted antlers.

Guesthouse in Dayton

Modern Farmhouse - Country living in wine country.

Escape to Oregon Wine Country! Light and bright modern farmhouse style rental . Enjoy a private suite in a detached barn with views of a country setting. King size bed with large Master suite and private patio. Queen size bed in a beautiful 2nd bedroom. Rental has a separate entrance in its own building. A 1800sf family/ rec room. Cozy fireplace, full kitchen, washer and dryer. Outdoor dining table on the patio. Located just one mile from Stoller Family & many more. Owners on site to assist

4.97 out of 5 average rating, 428 reviews

A two-story home surrounded by verdant vineyards and orchards is powered by solar panels on its roof. The structure features spacious balconies and is integrated into the natural landscape, with well-kept gardens and trees providing a serene atmosphere.

Farm stay in Newberg

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. Note that while the photos show our house when it was green, it has recently been repainted blue.

4.99 out of 5 average rating, 213 reviews

A charming yellow house is surrounded by vibrant gardens, featuring a variety of plants and flowers. Two red chairs are positioned outside, offering a peaceful spot to enjoy the greenery. Sunlight filters through the trees, illuminating the inviting exterior of the home.

Loft in Newberg

Friends' Cottage

Comfortable, well lit upstairs living area over our home. Currently we have 2 bedrooms available, plus a full bath with corner shower, sitting area, dining table, microwave, full size fridge. Windows look out onto a quiet neighborhood, backyard and gardens. Located near the heart of Newberg's rich downtown district, close to parks, coffee shops, beer and wine tasting, farm to table restaurants, antique stores, movie theater, grocery store and Cultural Center. Garden-fresh breakfast included.

4.93 out of 5 average rating, 152 reviews

A cozy seating area is highlighted by a warm brown sofa, complemented by a patterned armchair and a small side table. An open kitchen space is visible in the background, featuring a bar with three stools and natural light streaming through large windows.

Farm stay in Newberg

The Cellar @Lively Farm

Enjoy our little slice of hobby farm heaven nestled among the old-growth forest along Chehalem Creek. You'll experience the beauty of nature, the antics of our goats, chickens, rabbits, geese, ducks, and quail, and the charm of downtown Newberg. Our secluded neighborhood offers the perfect area for walking, running, or bike riding, and the wineries of Dundee are so close! Be warned that we live on the edge of the forest. Owls, deer, raccoons, squirrels, possums, and foxes frequent our yard.

4.92 out of 5 average rating, 235 reviews

A charming farmhouse is set amidst lush greenery, featuring a sloped roof and front porch. Surrounding the house are well-maintained trees and shrubs, complementing the vibrant lawn. The setting is tranquil, offering a serene escape in a natural environment.

Guest suite in Dundee

Pinot Paradise in Dundee Hills

Beautiful wine country guest suite and property in a stunning setting. 2 bedroom / 1 bath, sleeps 5. Located in the heart of Dundee Hills on 3 acres of picturesque farmland, offering a peaceful getaway and quick access to local wineries and restaurants. Private entrance, parking, wifi, fire pit (wood and smores kit provided!) , goats, creek, and much more to enjoy. Great for a couple's getaway, girls/guys weekend, family vacation, or personal retreat. A slice of heaven in wine country!

An outdoor space features a stone patio illuminated by string lights overhead. Four chairs surround a fire pit, inviting relaxation. A wooden bench extends along one side, and planters with greenery adorn the perimeter, enhancing the cozy atmosphere.

4.95 out of 5 average rating, 153 reviews

Closest to Town• Firepit •Deck •BBQ• Custom Design

👣 Effortlessly walk to premier wineries, local breweries and celebrated dining locations. We're in the heart of Dundee. Features: • Walk to tasting rooms, restaurants & Red Hills Market • 3 bedrooms (& den), 2 baths, sleeps 8 • Private backyard with fire pit, deck, canopy & BBQ • Single-level layout, self check-in, parking for 3 cars • Resort style outdoor area; couches, umbrella's, canopy, gas BBQ & Firepit • High Speed Wifi • Fully stocked kitchen Tip: ❤️ us to easily find again.

4.98 out of 5 average rating, 393 reviews

Buena Vista Farmhouse | Dundee Hills Guesthouse

WELCOME Tucked up among the vineyards of Dundee Hills, our modern vintage farmhouse guesthouse offers a peaceful wine country escape just steps from world-class tasting rooms. Three exceptional wineries are a short-five minute walk away—Lange Estate Winery, Torii Mor Winery and Elevee Winegrowers making this the perfect getaway. Director of guest experiences 🐾 Our friendly rescue dog Sequoia lives on the property and may stop by to say hello. Throwing her tennis ball optional.

A charming home is framed by vibrant bushes of blue flowers, with a large tree providing shade in the foreground. Lush greenery surrounds the property, complementing the inviting exterior of the house under a clear blue sky.

4.94 out of 5 average rating, 266 reviews

Chateau Lesieutre atop Dundee Hills’ Highest Point

Wake up above the Willamette Valley, surrounded by Oregon’s most celebrated wineries. Located at the highest point in Dundee, this serene retreat offers exquisite views. Sip your morning coffee on the terrace, enjoying the fresh country air and feeling as though you’re floating above the hills. With more than 10 wineries within two miles, it’s an ideal base for exploring wine country. After a day out, return home to unwind with evening stargazing in the courtyard or on the terrace.

4.92 out of 5 average rating, 748 reviews

The building, featuring the word 'MARKET' prominently, is framed by vibrant trees displaying autumn leaves. A welcoming entrance is complemented by outdoor seating arrangements, adding to the inviting atmosphere of the space.

Loft in Dundee

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!

4.97 out of 5 average rating, 281 reviews

The exterior of a Victorian-style home features a gray façade with a centered red door. Symmetrical windows flank the entrance, surrounded by manicured shrubbery and a well-kept lawn. Tall trees provide a lush backdrop under a clear blue sky.

Home in Dayton

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.

The exterior of a two-story white cottage is shown, featuring a double garage and a welcoming front porch. Lush green grass and landscaped flower beds enhance the curb appeal. Clear blue skies complement the inviting atmosphere created by the vibrant foliage on either side.

4.97 out of 5 average rating, 158 reviews

Charming Wine Retreat w/ Kid + Dog Perks

Come check out the Cloud Wine Cottage. Easily WALK to 8 different wineries (all in less than 10 minutes) and drive to more than 600+ more! Live like a local in wine country as you enjoy downtown Dundee with a park view. With 4 bedrooms, 2.5 bathrooms, and 7 beds, this beautiful vacation home is perfect for a group of friends or a family with kids. The property is pet-friendly with no extra fees.

4.94 out of 5 average rating, 1135 reviews

An inviting living area features floor-to-ceiling windows that offer views of the surrounding forest. Minimalist furniture includes a wooden table, lounge chairs, and a futon, creating a comfortable space to relax or entertain. Natural light enhances the cozy atmosphere.

Apartment in Newberg

Bright, Unique Apartment in Heart of Wine Country

*4 Min to George Fox University *10 Min walk to wine tasting rooms & restaurants *50+ wineries within 10 min drive This adorable daylight basement apartment is like walking into a storybook oasis. You’ll love the forest views from the floor to ceiling windows. Enjoy your morning coffee (or evening wine) from the private seating area and take in the sounds of chirping birds and babbling brook.

Popular amenities for Dundee family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5.0 out of 5 average rating, 103 reviews

Chic Newberg Oasis: Mid-Century, Hot Tub, Fire Pit

A tranquil outdoor space features two wooden chairs and a round table, positioned to enjoy a breathtaking sunset. The sky is adorned with vibrant purple and orange clouds, casting a serene light over the landscape below.

4.96 out of 5 average rating, 272 reviews

Parrett Mtn Estate · Hot Tub, Sauna & Valley Views

5.0 out of 5 average rating, 734 reviews

A hot tub with bubbling water sits beside a wooden sauna structure, designed with intricate detailing. The surrounding area features a pebble pathway and lush greenery, creating a tranquil outdoor setting.

Tiny home in Newberg

Garden Spa Getaway in Wine Country-Newberg

A spacious outdoor deck features a white Adirondack chair overlooking a vast landscape. The view encompasses rolling hills and a horizon that fades into the distance under a clear sky. Hues of autumn are visible in the trees and ground, adding color to the scenery.

4.94 out of 5 average rating, 238 reviews

Spectacular Valley View in Wine Country

5.0 out of 5 average rating, 102 reviews

A charming modern farmhouse features a light-colored exterior with a welcoming blue front door. The spacious front porch is equipped with wooden railing and comfortable seating. Lush greenery and mature trees frame the property, providing a serene and inviting setting.

Home in Carlton

Modern Farmhouse - Hot Tub

4.83 out of 5 average rating, 546 reviews

Treehouse in Portland

Yeti's Tree House: Where Dreams Come True

The front exterior of a well-maintained home is showcased, featuring a combination of earthy tones in its siding. A welcoming entrance is framed by lush landscaping, including ornamental grasses and flowering plants. A covered porch is visible, complemented by comfortable seating.

5.0 out of 5 average rating, 136 reviews

La Brise (A rest along the way)

4.99 out of 5 average rating, 193 reviews

A charming craftsman home is framed by a white picket fence, with a welcoming front porch and a pergola overhead. The exterior features dark blue siding, three front-facing windows, and lush greenery surrounding the entrance.

Home in Sherwood

Old Town Retreat - Best place in Old Town Sherwood

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 125 reviews

Guest suite in Dundee

Seventh Haven: A king suite in the heart of Dundee

Superhost

The exterior of the farmhouse is depicted, showcasing a traditional style with white siding and a steeply pitched roof. A small wooden deck is featured in the backyard, accompanied by two rustic chairs. Sunlight filters through nearby trees, enhancing the serene outdoor setting.

Home in McMinnville

Farmhouse • Chef's Kitchen• Firepit • Pet Friendly

4.87 out of 5 average rating, 158 reviews

4.96 out of 5 average rating, 141 reviews

Home in Carlton

Walk to Tasting Rooms | Firepit | Dog-Friendly

4.95 out of 5 average rating, 212 reviews

The brick home is set against a clear blue sky, surrounded by a manicured lawn. A winding driveway leads to the entrance, with colorful flowerbeds and shrubs enhancing the landscape. The structure features large windows that provide scenic views of the surrounding farm.

Farm stay in McMinnville

McMinnville Farm with a view, close to town!

4.99 out of 5 average rating, 107 reviews

A bright living room features a comfortable gray sofa and a light-colored armchair, accompanied by a coffee table. A large area rug with intricate patterns is centered on the floor. Natural light enters through nearby windows, and a small plant adds a touch of greenery.

Home in Carlton

Charming Cuvée Cottage

4.95 out of 5 average rating, 185 reviews

A handcrafted yurt is nestled among lush greenery, surrounded by tall trees. The structure features a round shape with a white exterior and decorative wooden lattice windows. In the foreground, a stack of firewood is visible, indicating readiness for cozy fires.

Yurt in McMinnville

Amico Roma Year Round Yurt and Sauna

4.97 out of 5 average rating, 299 reviews

The charming round house, surrounded by lush greenery, features large windows and a spacious deck. Vibrant flowers and ferns adorn the garden, contributing to the serene setting. Tall trees provide shade, framing a glimpse of the expansive landscape beyond.

Dome in Amity

Round House Retreat in the Woods

4.98 out of 5 average rating, 239 reviews

An aerial view captures a sprawling estate surrounded by lush greenery and mature trees. The main house stands prominently among manicured lawns, while additional outbuildings are visible nearby. A winding driveway leads to the entrance, enhancing the serene country atmosphere.

Home in Wilsonville

Beautiful Dog Friendly Cottage on a 10 Acre Estate

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 526 reviews

Guesthouse in Newberg

Wine Country Spa House - Hot Tub/Sauna/Pool

Superhost

Cabin in Newberg

A Rustic, Lodge Retreat with Pool, Hot Tub & More

4.96 out of 5 average rating, 113 reviews

4.93 out of 5 average rating, 117 reviews

An oversized covered patio features comfortable seating arranged around a central firepit. Soft lighting from hanging fixtures enhances the outdoor space, which is surrounded by greenery. The area is designed for relaxation and socializing, providing a welcoming atmosphere for guests.

Home in Woodburn

An Entertainment Oasis!

Guesthouse in Southwest Portland

Casetta

4.99 out of 5 average rating, 105 reviews

4.91 out of 5 average rating, 130 reviews

A covered patio area features a modern grill adjacent to a fire pit with flames flickering over stone. Comfortable seating is arranged around the fire pit, surrounded by lush greenery and stacked firewood along the back wall.

Apartment in Beaverton

Recreational Family Fun & Adventures Await

Guesthouse in Northwest Portland

The guest house is set against a lush backdrop of greenery, featuring large windows that provide views of the surrounding nature. A pool is positioned in front, accompanied by two wooden lounge chairs and a shaded umbrella, creating a serene outdoor relaxation area.

Poolhouse of Portland Architectural Gem

4.92 out of 5 average rating, 115 reviews

4.99 out of 5 average rating, 117 reviews

A spacious living area is highlighted by a warm brown leather seating arrangement, including two armchairs and a three-seat sofa. Natural light filters through the dual windows with rolled shades, complemented by two potted plants and a contemporary area rug.

Home in Portland

Corner of Heaven