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

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  6.  Oswego Hills Vineyard and Winery

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103 Best Family Vacation Rentals in Oswego Hills Vineyard and Winery (Starting from $92)

Lake Oswego Home with Covered Patio Near Portland!
Lake Oswego Home with Covered Patio Near Portland!
House
Lake Oswego, OR, USA
2.6k from Oswego Hills Vineyard and Winery center

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

3 Bedrooms8 Guests
7.0

Good

1 reviews

$360
Average price / night
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Countryside pet-friendly bungalow with a pool, just 20 minutes from Portland
Countryside pet-friendly bungalow with a pool, just 20 minutes from Portland
House
West Linn, OR, 97068, United States
1.1k from Oswego Hills Vineyard and Winery center

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

2 Bedrooms6 Guests
10.0

Exceptional

11 reviews

$342
Average price / night
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Riverside at the Riverhouse
Riverside at the Riverhouse
House
Milwaukie, OR, USA
2.9k from Oswego Hills Vineyard and Winery center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$328
Average price / night
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The TreeHouse Too - 2 BR Attached In-Law Flat/Apt. w/ Spa & Mucho Amenities .
The TreeHouse Too - 2 BR Attached In-Law Flat/Apt. w/ Spa & Mucho Amenities .
Apartment
West Linn, OR, 97068, United States
1.7k from Oswego Hills Vineyard and Winery center

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

3 Bedrooms8 Guests
4.8

Review score

13 reviews

$251
Average price / night
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Cozy River Forest Retreat
Cozy River Forest Retreat
House
Oak Grove, OR, USA
3.1k from Oswego Hills Vineyard and Winery center

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

3 Bedrooms6 Guests
New to Booking
$382
Average price / night
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Stafford River House
Stafford River House
House
West Linn, OR, 97068, United States
2.1k from Oswego Hills Vineyard and Winery center

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

3 Bedrooms7 Guests
9.0

Fabulous

53 reviews

$370
Average price / night
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Apollo Heights
Apollo Heights
House
West Linn, OR, USA
3.2k from Oswego Hills Vineyard and Winery center

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

4 Bedrooms12 Guests
5.0

Review score

1 reviews

$226
Average price / night
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Riverfront Garden House with private river access
Riverfront Garden House with private river access
House
West Linn, OR, 97068, United States
2.5k from Oswego Hills Vineyard and Winery center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
9.6

Exceptional

20 reviews

$455
Average price / night
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Dog-Friendly Milwaukie Home 9 Mi to Dtwn Portland
Dog-Friendly Milwaukie Home 9 Mi to Dtwn Portland
House
Milwaukie, OR, USA
3.4k from Oswego Hills Vineyard and Winery center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$274
Average price / night
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Rare Riverside Retreat
Rare Riverside Retreat
House
Oak Grove, OR, 97267, United States
3.2k from Oswego Hills Vineyard and Winery center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub

1 Bedroom3 Guests
9.8

Exceptional

20 reviews

$169
Average price / night
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Milwaukie Home with Covered Porch Dogs Welcome!
Milwaukie Home with Covered Porch Dogs Welcome!
House
Milwaukie, OR, USA
3.4k from Oswego Hills Vineyard and Winery center

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

3 Bedrooms6 Guests
New to Booking
$274
Average price / night
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West Linn modern 2 rooms, EV charger, patio, fire pit, forest view, deer glazing
West Linn modern 2 rooms, EV charger, patio, fire pit, forest view, deer glazing
House
West Linn, OR, 97068, United States
3.3k from Oswego Hills Vineyard and Winery center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
8.6

Fabulous

23 reviews

$220
Average price / night
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Riverwood Retreat
Riverwood Retreat
House
West Linn, OR, USA
3.4k from Oswego Hills Vineyard and Winery center

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

1 Bedroom6 Guests
New to Booking
$511
Average price / night
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Tanner Basin Retreat
Tanner Basin Retreat
House
West Linn, OR, USA
3.5k from Oswego Hills Vineyard and Winery center

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

1 Bedroom14 Guests
9.0

Fabulous

1 reviews

$965
Average price / night
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Beautiful Italian-style Villa in Lake Oswego
Beautiful Italian-style Villa in Lake Oswego
House
Lake Oswego, OR, 97035, United States
3.5k from Oswego Hills Vineyard and Winery center

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

3 Bedrooms6 Guests
New to Booking
$403
Average price / night
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Goat Shed
Goat Shed
House
West Linn, OR, USA
3.5k from Oswego Hills Vineyard and Winery center

Pet Friendly, Security/Safety, Parking, Barbecue/Outdoor Cooking, Child Friendly

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$404
Average price / night
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Captivating and Charming Retreat, Game Rooms, Pool Table, Pop a Shot, Foosball, 20 Min to Portland
Captivating and Charming Retreat, Game Rooms, Pool Table, Pop a Shot, Foosball, 20 Min to Portland
House
West Linn, OR, 97068, United States
3.5k from Oswego Hills Vineyard and Winery center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet

6 Bedrooms14 Guests
9.6

Exceptional

62 reviews

$715
Average price / night
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Marv's Place
Marv's Place
House
West Linn, OR, USA
3.5k from Oswego Hills Vineyard and Winery center

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

1 Bedroom2 Guests
New to Booking
$290
Average price / night
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Cowboy Cabana! Hot Tub and Ping Pong! Cozy 3 bedroom home.
Cowboy Cabana! Hot Tub and Ping Pong! Cozy 3 bedroom home.
House
Milwaukie, OR, 97267, United States
3.6k from Oswego Hills Vineyard and Winery center

AC, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.6

Exceptional

12 reviews

$371
Average price / night
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River Forest Retreat
River Forest Retreat
House
Milwaukie, OR, USA
3.5k from Oswego Hills Vineyard and Winery center

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

1 Bedroom12 Guests
New to Booking
$748
Average price / night
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Oswego Lake Country Club's 9th Fairway   \nAn ADU for 31+ days - \"The Bentley\"
Oswego Lake Country Club's 9th Fairway \nAn ADU for 31+ days - \"The Bentley\"
House
Lake Oswego, OR, 97034, United States
3.6k from Oswego Hills Vineyard and Winery center

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

1 Bedroom2 Guests
9.8

Exceptional

7 reviews

$92
Average price / night
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Portland Home w/ Private Hot Tub: 9 Mi to Downtown
Portland Home w/ Private Hot Tub: 9 Mi to Downtown
House
Milwaukie, OR, 97267, United States
4.0k from Oswego Hills Vineyard and Winery center

AC, Arcade, Barbecue, Crib, Extra Bed, Free Parking, Heater, Hot Tub, Kitchen

4 Bedrooms8 Guests
9.2

Superb

56 reviews

$341
Average price / night
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Newly Renovated Lake Oswego Home for the Summer ! Central and Walkable
Newly Renovated Lake Oswego Home for the Summer ! Central and Walkable
House
Lake Oswego, OR, 97035, United States
4.3k from Oswego Hills Vineyard and Winery center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms9 Guests
9.8

Exceptional

10 reviews

$697
Average price / night
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Pool and Hot Tub House West Linn, OR
Pool and Hot Tub House West Linn, OR
House
West Linn, OR, 97068, United States
4.3k from Oswego Hills Vineyard and Winery center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave

3 Bedrooms5 Guests
9.4

Superb

23 reviews

$231
Average price / night
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Premium 30+ Day Stay - Corporate & Insurance
Premium 30+ Day Stay - Corporate & Insurance
House
Lake Oswego, OR, 97035, United States
4.7k from Oswego Hills Vineyard and Winery center

AC, Crib, Dryer, Extra Bed, Free Parking, Heater, Kitchen, Living Area, Microwave

3 Bedrooms8 Guests
New to Booking
$227
Average price / night
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Extended Stay • Walk to Restaurants Cafés & Food Carts  • Patio Large Yard • Pet
Extended Stay • Walk to Restaurants Cafés & Food Carts • Patio Large Yard • Pet
House
West Linn, OR, 97068, United States
4.8k from Oswego Hills Vineyard and Winery center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
8.4

Very Good

11 reviews

$211
Average price / night
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Blue Heron Sanctuary · Private Riverfront Cottage Retreat
Blue Heron Sanctuary · Private Riverfront Cottage Retreat
Cottage
West Linn, OR, 97068, United States
5.1k from Oswego Hills Vineyard and Winery center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater

1 Bedroom4 Guests
9.8

Exceptional

17 reviews

$256
Average price / night
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Other accommodation types in Oswego Hills 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 Oswego Hills Vineyard and Winery.

Where to stay in Oswego Hills Vineyard and Winery? Best neighborhoods & areas

Oswego Hills Vineyard and Winery Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 103 verified family-friendly vacation rentals in Oswego Hills Vineyard and Winery. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Oswego Hills Vineyard and Winery vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $92 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Oswego Hills 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 Oswego Hills 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 Oswego Hills Vineyard and Winery often include amenities such as Child Friendly, Fireplace/Heating, and Laundry. 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.