Family-Friendly Vacation Rentals in Winderlea Vineyard and Winery, OR: Compare 10+ Sites & Save

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62 Best Family Vacation Rentals in Winderlea Vineyard and Winery (Starting from $122)

Trellis at Baptista Maresh Vineyard
Trellis at Baptista Maresh Vineyard
House
Dundee, OR, USA
0.3k from Winderlea Vineyard and Winery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$958
Average price / night
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Oregon Wine Country Hillside Retreat w/4 bedrooms, 3 baths.
Oregon Wine Country Hillside Retreat w/4 bedrooms, 3 baths.
House
Dundee, OR, 97115, United States
1.7k from Winderlea Vineyard and Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
New to Booking
$551
Average price / night
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Pinot Vista
Pinot Vista
House
Dundee, OR, USA
1.0k from Winderlea Vineyard and Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom14 Guests
New to Booking
$220
Average price / night
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Lovely Dundee Home w/ Private Yard & Fire Pit!
Lovely Dundee Home w/ Private Yard & Fire Pit!
House
Dundee, OR, 97115, United States
1.9k from Winderlea Vineyard and Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
8.8

Fabulous

3 reviews

$359
Average price / night
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Courtyard Cottage
Courtyard Cottage
House
Dundee, OR, USA
1.1k from Winderlea Vineyard and Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

4 Bedrooms12 Guests
New to Booking
$1020
Average price / night
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5 Bed Private Villa in Wine Country w/ Pool, Sauna, Hot Tub
5 Bed Private Villa in Wine Country w/ Pool, Sauna, Hot Tub
Villa
Dundee, OR, 97115, United States
2.0k from Winderlea Vineyard and Winery center

AC, Balcony, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms10 Guests
New to Booking
$1376
Average price / night
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Dundee Hills Villa
Dundee Hills Villa
House
Dundee, OR, USA
1.1k from Winderlea Vineyard and Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis, Places to stay

1 Bedroom12 Guests
New to Booking
$470
Average price / night
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3 Bed Private Villa in Wine Country with Pool + Hot Tub
3 Bed Private Villa in Wine Country with Pool + Hot Tub
House
Dundee, OR, 97115, United States
2.0k from Winderlea Vineyard and Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Laundry, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

8 reviews

$1312
Average price / night
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A Taste Of Dundee
A Taste Of Dundee
House
Dundee, OR, USA
1.7k from Winderlea Vineyard and Winery center

Parking, Hot Tub, Air Conditioner, Internet, Balcony/Terrace, Child Friendly

1 Bedroom3 Guests
9.2

Superb

5 reviews

$124
Average price / night
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Sunny home with enclosed yard, grill, fast WiFi, washer/dryer, & outdoor dining
Sunny home with enclosed yard, grill, fast WiFi, washer/dryer, & outdoor dining
House
Dundee, OR, 97115, United States
2.1k from Winderlea Vineyard and Winery center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.2

Superb

25 reviews

$291
Average price / night
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Lovely Dundee Home with Private Yard and Fire Pit!
Lovely Dundee Home with Private Yard and Fire Pit!
House
Dundee, OR, USA
1.9k from Winderlea Vineyard and Winery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$421
Average price / night
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Incredible Dundee Hills Escape, Pet Friendly, Hot Tub, Covered Deck, Walk to Park, Food, and Wine
Incredible Dundee Hills Escape, Pet Friendly, Hot Tub, Covered Deck, Walk to Park, Food, and Wine
House
Dundee, OR, 97115, United States
2.3k from Winderlea Vineyard and Winery center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
9.8

Exceptional

50 reviews

$812
Average price / night
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Casa Dundee
Casa Dundee
House
Dundee, OR, USA
2.1k from Winderlea Vineyard and Winery center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
9.0

Fabulous

5 reviews

$188
Average price / night
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Escape to Wine Country, Luxurious Getaway Awaits!
Escape to Wine Country, Luxurious Getaway Awaits!
House
Dundee, OR, 97115, United States
2.3k from Winderlea Vineyard and Winery center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

6 Bedrooms18 Guests
10.0

Exceptional

21 reviews

$2240
Average price / night
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Cozy place for families, couples & friends. Hot tub awaits. Central to activity.
Cozy place for families, couples & friends. Hot tub awaits. Central to activity.
House
Dundee, OR, 97115, United States
2.9k from Winderlea Vineyard and Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$351
Average price / night
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Dundee Wine Country View
Dundee Wine Country View
House
Dundee, OR, USA
2.3k from Winderlea Vineyard and Winery center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

3 Bedrooms6 Guests
7.3

Good

3 reviews

$148
Average price / night
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Modern 3 Bedroom Farmhouse of Dundee - Amazing Views, Fire Pit and Comfort
Modern 3 Bedroom Farmhouse of Dundee - Amazing Views, Fire Pit and Comfort
House
Dundee, OR, 97115, United States
3.1k from Winderlea Vineyard and Winery center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

22 reviews

$460
Average price / night
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Dogwood Villa
Dogwood Villa
House
Dundee, OR, USA
2.3k from Winderlea Vineyard and Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis, Places to stay

5 Bedrooms12 Guests
New to Booking
$872
Average price / night
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The Wayside: New in the Heart of Town
The Wayside: New in the Heart of Town
House
Dundee, OR, 97115, United States
3.1k from Winderlea Vineyard and Winery center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.2

Superb

10 reviews

$525
Average price / night
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Kef House
Kef House
House
Dundee, OR, USA
2.3k from Winderlea Vineyard and Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis, Places to stay

1 Bedroom12 Guests
New to Booking
$1056
Average price / night
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The Cellar @Lively Farm\na Family Friendly Hobby Farm Stay
The Cellar @Lively Farm\na Family Friendly Hobby Farm Stay
House
Newberg, OR, 97132, United States
4.2k from Winderlea Vineyard and Winery center

AC, Crib, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

2 Bedrooms7 Guests
10.0

Exceptional

11 reviews

$122
Average price / night
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Breathtaking Valley Views, Pet Friendly, Huge Deck, Fire-Pit, Air Hockey, Ping Pong, Near Vineyards
Breathtaking Valley Views, Pet Friendly, Huge Deck, Fire-Pit, Air Hockey, Ping Pong, Near Vineyards
House
Newberg, OR, 97132, United States
4.3k from Winderlea Vineyard and Winery center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms12 Guests
9.8

Exceptional

72 reviews

$1002
Average price / night
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Country Luxury in Private Manor, Pet Friendly, Hot Tub, Indoor Basketball Ct, Billiards, on 2 Acres
Country Luxury in Private Manor, Pet Friendly, Hot Tub, Indoor Basketball Ct, Billiards, on 2 Acres
House
Newberg, OR, 97132, United States
4.5k from Winderlea Vineyard and Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

6 Bedrooms12 Guests
10.0

Exceptional

60 reviews

$1790
Average price / night
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Book now for new 2026 specials! Fire-pit, garage games, wine country relaxing
Book now for new 2026 specials! Fire-pit, garage games, wine country relaxing
House
Newberg, OR, 97132, United States
5.8k from Winderlea Vineyard and Winery center

AC, Arcade, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms8 Guests
10.0

Exceptional

51 reviews

$503
Average price / night
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Beautiful 4 bedroom! Hot Tub, Fabulous Downtown Newberg Location!
Beautiful 4 bedroom! Hot Tub, Fabulous Downtown Newberg Location!
House
Newberg, OR, 97132, United States
5.9k from Winderlea Vineyard and Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms14 Guests
10.0

Exceptional

3 reviews

$901
Average price / night
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Luxury Flat in Downtown Newberg - Suite #5
Luxury Flat in Downtown Newberg - Suite #5
Condo
Newberg, OR, 97132, United States
5.9k from Winderlea Vineyard and Winery center

AC, Crib, Fireplace, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
9.8

Exceptional

50 reviews

$260
Average price / night
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Victorian Secrets 1897 Home - Curious? Eclectic, convenient & ❤️ of wine country
Victorian Secrets 1897 Home - Curious? Eclectic, convenient & ❤️ of wine country
House
Newberg, OR, 97132, United States
6.0k from Winderlea Vineyard and Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

89 reviews

$372
Average price / night
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Other accommodation types in Winderlea Vineyard and Winery:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Winderlea Vineyard and Winery.

Winderlea Vineyard and Winery Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 62 verified family-friendly vacation rentals in Winderlea Vineyard and Winery. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Winderlea Vineyard and Winery vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $122 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Winderlea Vineyard and Winery offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Winderlea Vineyard and Winery are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Winderlea Vineyard and Winery often include amenities such as Child Friendly, Wellness Facilities, and Fireplace/Heating. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.