Family-Friendly Vacation Rentals in Jackson-Triggs Winery, ON: Compare 10+ Sites & Save

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81 Best Family Vacation Rentals in Jackson-Triggs Winery (Starting from $119)

The Little White Haus
The Little White Haus
House
Niagara on the Lake, Canada
0.6k from Jackson-Triggs Winery center

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

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$351
Average price / night
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Luxury Old Town Winter Retreat- Hot Tub and Games
Luxury Old Town Winter Retreat- Hot Tub and Games
Villa
Niagara-on-the-Lake, Canada
0.8k from Jackson-Triggs Winery center

Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs

1 Bedroom10 Guests
7.5

Good

2 reviews

$482
Average price / night
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Spacious House - GREAT LOCATION in Old Town NOTL with HOT TUB & Univ. EV CHARGER
Spacious House - GREAT LOCATION in Old Town NOTL with HOT TUB & Univ. EV CHARGER
House
Niagara-on-the-Lake, L0S 1J0, Canada
0.7k from Jackson-Triggs Winery center

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

4 Bedrooms8 Guests
9.8

Exceptional

19 reviews

$582
Average price / night
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Dorchester Cottage Licence 044-2022
Dorchester Cottage Licence 044-2022
House
Niagara on the Lake, Canada
1.1k from Jackson-Triggs Winery center

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

3 Bedrooms8 Guests
9.2

Superb

17 reviews

$635
Average price / night
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 The Maplewood House - Walk to old town Niagara-on-the-Lake
The Maplewood House - Walk to old town Niagara-on-the-Lake
House
Niagara-on-the-Lake, L0S1J0, Canada
0.7k from Jackson-Triggs Winery center

AC, Arcade, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms8 Guests
10.0

Exceptional

236 reviews

$354
Average price / night
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Walk to Lake - Old Town Retreat
Walk to Lake - Old Town Retreat
Villa
Niagara-on-the-Lake, Canada
1.2k from Jackson-Triggs Winery center

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

4 Bedrooms8 Guests
8.4

Very Good

7 reviews

$433
Average price / night
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The Homestead - Luxury Cottage with Heated Pool in Historic Old Town NOTL
The Homestead - Luxury Cottage with Heated Pool in Historic Old Town NOTL
House
Niagara-on-the-Lake, L0S 1J0, Canada
0.8k from Jackson-Triggs Winery center

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

4 Bedrooms9 Guests
9.8

Exceptional

153 reviews

$438
Average price / night
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Canterbury Inn
Canterbury Inn
House
Jackson-Triggs Winery, Niagara-on-the-Lake, Ontario, Canada
1.2k from Jackson-Triggs Winery center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Romantic, Lodgings, Vacation rentals

6 Bedrooms14 Guests
8.9

Fabulous

559 reviews

$119
Average price / night
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The Pines, Circa 1850 in Old Town NOTL, with Heated Pool, Sleeps 10
The Pines, Circa 1850 in Old Town NOTL, with Heated Pool, Sleeps 10
House
Niagara-on-the-Lake, L0S 1J0, Canada
0.9k from Jackson-Triggs Winery center

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

4 Bedrooms10 Guests
9.8

Exceptional

35 reviews

$644
Average price / night
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Maple Tree Cottage License # 058-2022
Maple Tree Cottage License # 058-2022
House
Niagara on the Lake, Canada
1.2k from Jackson-Triggs Winery center

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

3 Bedrooms6 Guests
9.4

Superb

23 reviews

$281
Average price / night
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The Orchard House, 3 bedroom house in NOTL
The Orchard House, 3 bedroom house in NOTL
House
Niagara-on-the-Lake, L0S 1J0, Canada
0.9k from Jackson-Triggs Winery center

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

4 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$417
Average price / night
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Arrowstone Farmhouse in Historic Old Town
Arrowstone Farmhouse in Historic Old Town
House
Niagara on the Lake, Canada
1.2k from Jackson-Triggs Winery center

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

3 Bedrooms8 Guests
New to Booking
$442
Average price / night
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Happy House w/In-Ground Private Pool in NOTL
Happy House w/In-Ground Private Pool in NOTL
House
Niagara-on-the-Lake, L0S 1J0, Canada
1.0k from Jackson-Triggs Winery center

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

3 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$524
Average price / night
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Cozy Home in Niagara-on-the-Lake
Cozy Home in Niagara-on-the-Lake
House
Niagara on the Lake, Canada
1.3k from Jackson-Triggs Winery center

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

3 Bedrooms6 Guests
9.2

Superb

43 reviews

$288
Average price / night
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Mid-Century Cottage in Historic Old Town Niagara on the Lake, walk to amenities.
Mid-Century Cottage in Historic Old Town Niagara on the Lake, walk to amenities.
House
Niagara-on-the-Lake, L0S 1J0, Canada
1.1k from Jackson-Triggs Winery center

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

3 Bedrooms8 Guests
10.0

Exceptional

39 reviews

$445
Average price / night
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The Promenade Cottage License # 002-2023
The Promenade Cottage License # 002-2023
House
Niagara on the Lake, Canada
1.4k from Jackson-Triggs Winery center

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

3 Bedrooms6 Guests
9.1

Superb

30 reviews

$362
Average price / night
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Charming Old Town Cottage - Walk to Queen St & Wineries
Charming Old Town Cottage - Walk to Queen St & Wineries
House
Niagara-on-the-Lake, L0S 1J0, Canada
1.1k from Jackson-Triggs Winery center

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

2 Bedrooms5 Guests
10.0

Exceptional

27 reviews

$289
Average price / night
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Centre Gate House Licence# 117-2023
Centre Gate House Licence# 117-2023
Villa
Niagara on the Lake, Canada
1.5k from Jackson-Triggs Winery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1332
Average price / night
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Secret Garden Cottage in Old Town Niagara-on-the-Lake
Secret Garden Cottage in Old Town Niagara-on-the-Lake
House
Niagara-on-the-Lake, L0S 1J0, Canada
1.2k from Jackson-Triggs Winery center

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

2 Bedrooms7 Guests
10.0

Exceptional

69 reviews

$351
Average price / night
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Cellar House NOTL - Entire Home in the Heart of Niagara-on-the-Lake
Cellar House NOTL - Entire Home in the Heart of Niagara-on-the-Lake
House
Niagara on the Lake, Canada
1.5k from Jackson-Triggs Winery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Jacuzzis

4 Bedrooms8 Guests
9.8

Exceptional

5 reviews

$382
Average price / night
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A 4 Bedroom Vacation Rental with Heated Pool in Old Town Niagara on the Lake.
A 4 Bedroom Vacation Rental with Heated Pool in Old Town Niagara on the Lake.
House
Niagara-on-the-Lake, L0S 1J0, Canada
1.2k from Jackson-Triggs Winery center

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

4 Bedrooms10 Guests
9.8

Exceptional

67 reviews

$624
Average price / night
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FREE bottle of local Niagara On The Lake wine with every 3 or more nights booked
FREE bottle of local Niagara On The Lake wine with every 3 or more nights booked
House
Niagara-on-the-Lake, L0S1J0, Canada
1.4k from Jackson-Triggs Winery center

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

3 Bedrooms6 Guests
9.4

Superb

42 reviews

$304
Average price / night
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Top 1% Old Town Family Single Level Home  6 ppl
Top 1% Old Town Family Single Level Home 6 ppl
Apartment
Niagara-on-the-Lake, L0S 1J0, Canada
1.5k from Jackson-Triggs Winery center

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

3 Bedrooms6 Guests
New to Booking
$490
Average price / night
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Entire House Walking distance to downtown Niagara on the Lake
Entire House Walking distance to downtown Niagara on the Lake
House
Niagara-on-the-Lake, L0S 1J0, Canada
1.5k from Jackson-Triggs Winery center

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

3 Bedrooms7 Guests
9.6

Exceptional

82 reviews

$318
Average price / night
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Private spacious Home in the heart of Niagara-on-the-Lake's Historic District.
Private spacious Home in the heart of Niagara-on-the-Lake's Historic District.
House
Niagara-on-the-Lake, L0S 1J0, Canada
1.5k from Jackson-Triggs Winery center

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

3 Bedrooms8 Guests
9.8

Exceptional

8 reviews

$1045
Average price / night
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Cali House\nOld Town Niagara-on-The-Lake close to downtown
Cali House\nOld Town Niagara-on-The-Lake close to downtown
House
Niagara-on-the-Lake, L0S 1J0, Canada
1.6k from Jackson-Triggs Winery center

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

3 Bedrooms8 Guests
9.8

Exceptional

10 reviews

$429
Average price / night
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Charming Historic Cottage in Old Town Niagara-on-the-Lake
Charming Historic Cottage in Old Town Niagara-on-the-Lake
House
Niagara-on-the-Lake, L0S 1J0, Canada
1.6k from Jackson-Triggs Winery center

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

2 Bedrooms3 Guests
9.2

Superb

52 reviews

$331
Average price / night
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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 Jackson-Triggs Winery.

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Frequently Asked Questions

You can explore 81 verified family-friendly vacation rentals in Jackson-Triggs Winery. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Jackson-Triggs Winery vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $119 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Jackson-Triggs 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 Jackson-Triggs 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 Jackson-Triggs Winery often include amenities such as Child Friendly, Balcony/Terrace, and Internet. 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.