Family-Friendly Vacation Rentals in Applewood Winery, NY: Compare 10+ Sites & Save

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  6.  Applewood Winery

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57 Best Family Vacation Rentals in Applewood Winery (Starting from $148)

Craftsman Hideaway at the 1841 Farmhouse
Craftsman Hideaway at the 1841 Farmhouse
Apartment
Chester, NY, USA
2.9k from Applewood Winery center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom2 Guests
9.2

Superb

5 reviews

$229
Average price / night
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Mountain Luxury: Pool, Theater & Outdoor Kitchen
Mountain Luxury: Pool, Theater & Outdoor Kitchen
Ski Chalet
Warwick, NY, 10990, United States
2.4k from Applewood Winery center

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

6 Bedrooms10 Guests
10.0

Exceptional

13 reviews

$1208
Average price / night
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Millionare Mansion with Grill, Spa, Huge Deck,Views, Game Room, Hiking, More
Millionare Mansion with Grill, Spa, Huge Deck,Views, Game Room, Hiking, More
Apartment
Chester, NY, USA
5.8k from Applewood Winery center

Child Friendly, Parking, Kitchen, Breakfast, Balcony/Terrace, Internet, Smoking

4 Bedrooms10 Guests
New to Booking
$894
Average price / night
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Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
Apartment
Chester, NY, 10918, United States
3.2k from Applewood Winery center

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

2 Bedrooms6 Guests
10.0

Exceptional

55 reviews

$229
Average price / night
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Family Home Close to Warwick, 5 Mi to Lake!
Family Home Close to Warwick, 5 Mi to Lake!
House
Monroe, NY, USA
5.9k from Applewood Winery center

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

4 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$492
Average price / night
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Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
House
Warwick, NY, 10990, United States
3.4k from Applewood Winery center

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

4 Bedrooms8 Guests
9.8

Exceptional

18 reviews

$688
Average price / night
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KW homes
KW homes
House
NY, USA
6.0k from Applewood Winery center

B&bs, Accommodations, Parking, Guest houses, Homestays, Pet-friendly, Lodgings, Places to stay, Family

3 Bedrooms10 Guests
New to Booking
$374
Average price / night
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Mountain View Retreat w/ Hot Tub, Theater, and Gym
Mountain View Retreat w/ Hot Tub, Theater, and Gym
Ski Chalet
Warwick, NY, 10990, United States
3.8k from Applewood Winery center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1286
Average price / night
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Secluded 9BR Getaway, Pool, Hot Tub & Huge Deck
Secluded 9BR Getaway, Pool, Hot Tub & Huge Deck
Villa
Chester, NY, USA
6.3k from Applewood Winery center

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

9 Bedrooms28 Guests
New to Booking
$1991
Average price / night
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“Warwick Retreat Haven  Cozy, Quiet & Scenic”
“Warwick Retreat Haven Cozy, Quiet & Scenic”
House
Warwick, NY, 10990, United States
4.9k from Applewood Winery center

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

4 Bedrooms8 Guests
9.8

Exceptional

7 reviews

$444
Average price / night
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Hudson Valley Retreat with Pool Near Greenwood Lake
Hudson Valley Retreat with Pool Near Greenwood Lake
House
Monroe, NY, USA
6.4k from Applewood Winery center

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

2 Bedrooms4 Guests
New to Booking
$387
Average price / night
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Waterfall Cottage - Romantic Luxury Escape - nearby hiking, wineries and skiing
Waterfall Cottage - Romantic Luxury Escape - nearby hiking, wineries and skiing
House
Warwick, NY, 10990, United States
4.9k from Applewood Winery center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

1 Bedroom2 Guests
10.0

Exceptional

155 reviews

$249
Average price / night
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Huge Retreat w Alaska King, Pool & Jacuzzi Tub Indoor
Huge Retreat w Alaska King, Pool & Jacuzzi Tub Indoor
Villa
Goshen, NY, USA
6.6k from Applewood Winery center

Air Conditioner, Parking, Pet Friendly, Internet, Pool, Balcony/Terrace, Security/Safety

1 Bedroom13 Guests
New to Booking
$789
Average price / night
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Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Villa
Chester, NY, 10918, United States
5.9k from Applewood Winery center

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

7 Bedrooms16 Guests
9.6

Exceptional

13 reviews

$1676
Average price / night
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Elegant Home 7BRs, Game Room, Luxury Yard, Pool
Elegant Home 7BRs, Game Room, Luxury Yard, Pool
Apartment
Chester, NY, USA
6.7k from Applewood Winery center

Apartments, Luxury, Accommodations, Pools, Parking, Lodgings, Places to stay, Family

2 Bedrooms16 Guests
New to Booking
$882
Average price / night
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Grand 10BR Retreat w/Pool & Hot Tub
Grand 10BR Retreat w/Pool & Hot Tub
Villa
Chester, NY, 10918, United States
6.5k from Applewood Winery center

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

10 Bedrooms23 Guests
2.0

Review score

1 reviews

$2210
Average price / night
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Walton Lake Mountain Lodge
Walton Lake Mountain Lodge
House
Monroe, NY, USA
6.9k from Applewood Winery center

Laundry, Wheelchair Accessible, Pool, Hot Tub, Parking, Internet, Child Friendly

4 Bedrooms10 Guests
New to Booking
$498
Average price / night
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Amazing  Home Near West Point,  Shopping,  Skiing and Legoland
Amazing Home Near West Point, Shopping, Skiing and Legoland
House
Monroe, NY, 10950, United States
6.6k from Applewood Winery center

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

3 Bedrooms9 Guests
10.0

Exceptional

14 reviews

$593
Average price / night
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Relaxing New York Home with Boat Dock and Lake View!
Relaxing New York Home with Boat Dock and Lake View!
House
Monroe, NY, USA
7.1k from Applewood Winery center

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

4 Bedrooms6 Guests
7.5

Good

2 reviews

$289
Average price / night
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Stylish 3-Bedroom Home in the Village of Warwick
Stylish 3-Bedroom Home in the Village of Warwick
House
Warwick, NY, 10990, United States
6.6k from Applewood Winery center

AC, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$363
Average price / night
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Colonial-Style Warwick Retreat - 1 Hour to NYC!
Colonial-Style Warwick Retreat - 1 Hour to NYC!
House
Warwick, NY, USA
7.4k from Applewood Winery center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$432
Average price / night
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Charming  house surrounded lakes and the fresh air of the mountains
Charming house surrounded lakes and the fresh air of the mountains
House
Monroe, NY, 10950, United States
6.9k from Applewood Winery center

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

1 Bedroom6 Guests
9.6

Exceptional

19 reviews

$148
Average price / night
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11BR Retreat w Pool & Game Room
11BR Retreat w Pool & Game Room
Villa
Chester, NY, 10918, United States
7.2k from Applewood Winery center

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

11 Bedrooms28 Guests
New to Booking
$2617
Average price / night
Check Availability
NEW – TWO Side-by-Side Lake Homes Sleep 17 - 2 Private Docks -1 hr NYC pets ok
NEW – TWO Side-by-Side Lake Homes Sleep 17 - 2 Private Docks -1 hr NYC pets ok
House
Monroe, NY, 10950, United States
7.4k from Applewood Winery center

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

7 Bedrooms17 Guests
10.0

Exceptional

12 reviews

$2686
Average price / night
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Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
House
Greenwood Lake, NY, 10925, United States
7.7k from Applewood Winery center

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

3 Bedrooms6 Guests
9.8

Exceptional

37 reviews

$521
Average price / night
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Spectacular Historic Mansion w/Pool&Tennis
Spectacular Historic Mansion w/Pool&Tennis
House
Goshen, NY, 10924, United States
7.9k from Applewood Winery center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Heater, Hot Tub, Internet

10 Bedrooms25 Guests
10.0

Exceptional

18 reviews

$2382
Average price / night
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Lakefront Oasis 50mi from NYC. Game Room, Kayaks, Dock, Hot Tub Soon.
Lakefront Oasis 50mi from NYC. Game Room, Kayaks, Dock, Hot Tub Soon.
House
Greenwood Lake, NY, 10925, United States
7.9k from Applewood Winery center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$746
Average price / night
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Other accommodation types in Applewood 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 Applewood Winery.

Applewood Winery Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 57 verified family-friendly vacation rentals in Applewood Winery. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Applewood Winery vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $148 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Applewood 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 Applewood 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 Applewood Winery often include amenities such as Child Friendly, Fireplace/Heating, 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.