Family-friendly holiday rentals in Dundee

A cozy sleeping area is featured, with a white bed neatly arranged with patterned pillows. A vintage-style side table holds a tray with glasses and a bottle, alongside a small pot of blooming flowers. Soft light from a lamp provides a warm glow.

4.98 out of 5 average rating, 384 reviews

The Farmhouse at Red Hills|Dundee Wine Country

WELCOME Tucked up among the vineyards of Dundee Hills, our modern vintage farmhouse studio 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 Olenik Vineyards-making this the perfect getaway. Resident Greeter🐾 Our friendly rescue dog Sequoia lives on the property and may stop by to say hello if she is outside. She believes every guest is her new best friend.

KitchenIndoor spacesNearby

5.0 out of 5 average rating, 206 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

KitchenIndoor spacesBreakfast

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, 271 reviews

Parrett Mtn Estate · Hot Tub, Sauna & Valley Views

8 private acres atop Parrett Mountain — sweeping Pinot Noir vineyard & valley views, Tempur-Pedic suites & heated stone floors. The only estate in Willamette Valley with an Oregon Red Cedar sauna, cold plunge, starlit hot tub & Universal EV Charging. Two full chef's kitchens, Egyptian cotton linens, Dyson air purifiers & hair tools, 4 bedrooms, sleeps 12. Optional add-ons available: private chef, Sommelier wine tasting & concierge services. 5 min to Newberg · 30 min to Portland · 40 min to PDX.

Indoor spacesKitchenNearby

4.97 out of 5 average rating, 423 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.

FamilyKitchenComfort

4.91 out of 5 average rating, 374 reviews

Guest suite in Newberg

Red Hills Retreat — Lower Carriage House

Welcome to our cozy studio apartment, a refined and serene sanctuary nestled amid the beauty of Oregon's Willamette Valley wine country. This elegant, generously proportioned suite offers a full private bathroom and a fully equipped kitchenette, thoughtfully designed for comfort and convenience during your stay. The apartment sits on our 10-acre hobby farm at the end of a mile-long lane bordered by hazelnut trees, vineyards, and pastures—giving you a quiet, private spot surrounded by nature.

KitchenFamilyHospitality

4.95 out of 5 average rating, 147 reviews

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

💯 Perfectly situated in the heart of Dundee. 👣 Effortlessly walk to premier wineries, local breweries and celebrated dining locations. What to look forward to during your stay: Features: • 5 beds; 1 king en-suite, 2 queens, 2 twin trundles in den • High Speed Wifi & Bose Bar • Large, custom dining area, wainscoted walls, custom light ring • Fully stocked kitchen • Resort style outdoor area; couches, umbrella's, retractable canopy, gas BBQ & Firepit Tip: ❤️ us to easily find again.

FamilyIndoor spacesParking

4.93 out of 5 average rating, 148 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.

FamilyKitchenGetting around

4.92 out of 5 average rating, 231 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!

KitchenIndoor spacesBackyard

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.

4.93 out of 5 average rating, 259 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.

KitchenFamilyDecor

4.92 out of 5 average rating, 740 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!

Indoor spacesFamilyNearby

5.0 out of 5 average rating, 730 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

Enjoy the hot tub & sauna for relaxation! The Tiny Home is privately tucked in a garden oasis, in a quiet residential neighborhood. Only 13 blocks to downtown Newberg 's wine boutiques & restaurants, 6 blocks to George Fox University, 45 min. from PDX Airport. Spacious with 192 sq. feet of modern comfort. Complimentary specialty cheese & oatmeal cups for breakfast. Nice bikes to tour Newberg & local wine boutiques. *Two night minimum stay. *E-Bike Seated Scooters available.

KitchenIndoor spacesRiver

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, 152 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.

KitchenIndoor spacesAccess

Popular amenities for Dundee family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 132 reviews

La Brise (A rest along the way)

FamilyIndoor spacesHot tub

4.82 out of 5 average rating, 536 reviews

Treehouse in Portland

Yeti's Tree House: Where Dreams Come True

FamilyKitchenWalkability

4.95 out of 5 average rating, 735 reviews

A vibrant sunset fills the sky with shades of orange, pink, and purple, casting a warm glow over the silhouetted treetops. The horizon is lined with distant mountains, creating a serene backdrop to this stunning natural display.

Apartment in Hillsboro

Wine country retreat with amazing views

Indoor spacesKitchenAccess

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, 234 reviews

Spectacular Valley View in Wine Country

Indoor spacesFamilyBarbecue

4.98 out of 5 average rating, 235 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

KitchenIndoor spacesHiking

Home in Southwest Portland

A mid-century living space features high vaulted wood ceilings and large windows that invite natural light. A leather sofa and patterned rug provide comfort, while a kitchen island with bar stools enhances functionality. Artwork adorns the wall, adding a touch of character to the room.

4.96 out of 5 average rating, 160 reviews

Portland Modern

KitchenIndoor spacesHospitality

4.99 out of 5 average rating, 189 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

Indoor spacesKitchenOutdoor spaces

Home in Southwest Portland

A spacious family room features a large L-shaped couch with comfortable seating. A plush green ottoman rests on a striped rug, complementing a contemporary armchair. Natural light filters through multiple windows, illuminating the room, which includes a TV and a cozy gas-lit fireplace.

4.93 out of 5 average rating, 296 reviews

Spacious Forest Retreat w/ Hot Tub & Views

Indoor spacesFamilyDecor

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 279 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

FamilyIndoor spacesQuiet

4.95 out of 5 average rating, 204 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!

Indoor spacesFamilyRiver

4.99 out of 5 average rating, 100 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

KitchenIndoor spacesAccess

A welcoming living area is featured, with comfortable seating arrangements including a dark leather couch and light-colored armchairs. A wooden coffee table sits in the center of a vibrant area rug. Natural light enters through large windows, enhancing the inviting atmosphere.

4.98 out of 5 average rating, 403 reviews

College Street House

FamilyKitchenComfort

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

4.86 out of 5 average rating, 152 reviews

Farmhouse • Chef's Kitchen• Firepit • Pet Friendly

KitchenFamilyView

4.99 out of 5 average rating, 289 reviews

A century-old cottage is framed by lush gardens and tall trees. The vibrant red exterior is complemented by inviting porches and white railings. A gravel pathway leads to a cozy seating area, surrounded by an array of plants and foliage, enhancing the tranquil setting.

Home in Portland

Hidden Garden Cottage

KitchenIndoor spacesComfort

4.92 out of 5 average rating, 219 reviews

An outdoor picnic table is positioned on a bed of natural mulch, surrounded by towering trees. The tiny house, featuring a red and white exterior, is visible in the background, complemented by a small fenced area and a grill.

Tiny home in Sherwood

Winery Getaway Pets Welcome BBQ & Fresh Air Shower

FamilyKitchenParks

4.96 out of 5 average rating, 235 reviews

The exterior of the Tiny Home features a welcoming wooden deck with stairs leading up. Flower pots filled with greenery flank the steps, while large windows allow natural light to illuminate the interior. A vibrant front door adds a pop of color against the dark siding.

Tiny home in Beaverton

Beaverton Vintage Tiny Home

KitchenFamilySleep quality

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 518 reviews

Guesthouse in Newberg

Wine Country Spa House - Hot Tub/Sauna/Pool

KitchenIndoor spacesSleep quality

4.93 out of 5 average rating, 108 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!

FamilyIndoor spacesBarbecue

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.

4.92 out of 5 average rating, 108 reviews

Poolhouse of Portland Architectural Gem

KitchenIndoor spacesQuiet

4.9 out of 5 average rating, 123 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

Indoor spacesFamilyCheck-in

4.99 out of 5 average rating, 114 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

FamilyKitchenAir conditioning

4.97 out of 5 average rating, 393 reviews

A cozy sleeping space features a spacious bed adorned with various patterned pillows and a chunky knit blanket. A small yellow ottoman sits beside the bed, while artwork in soft colors is displayed on the light gray walls. A light rug adds warmth to the floor.

Cottage in Portland

Sellwood Sanctuary Guest House

FamilyIndoor spacesValue