Family-Friendly Vacation Rentals in Highlands Country Club, NY: Compare 10+ Sites & Save

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29 Best Family Vacation Rentals in Highlands Country Club (Starting from $98)

Walk 2mins to West Point Academy! Free private parking WiFi
Walk 2mins to West Point Academy! Free private parking WiFi
Apartment
Highland Falls, NY, USA
1.7k from Highlands Country Club center

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

4 Bedrooms10 Guests
8.6

Fabulous

5 reviews

$293
Average price / night
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Updated Home w/ Patio Half Mile to West Point
Updated Home w/ Patio Half Mile to West Point
House
Highland Falls, NY, 10928, United States
1.9k from Highlands Country Club center

AC, Crib, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

32 reviews

$380
Average price / night
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WALK to West Point Academy! Charming 2 bdrm Apt overlooking Main Street!
WALK to West Point Academy! Charming 2 bdrm Apt overlooking Main Street!
Apartment
Highland Falls, NY, USA
1.7k from Highlands Country Club center

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

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$325
Average price / night
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Garrison Getaway | Pool, Sauna & Gym
Garrison Getaway | Pool, Sauna & Gym
House
Garrison, NY, 10524, United States
2.0k from Highlands Country Club center

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

3 Bedrooms6 Guests
New to Booking
$1956
Average price / night
Check Availability
Beautiful 2BR Apartment-, Walk To West Point, Free Parking!
Beautiful 2BR Apartment-, Walk To West Point, Free Parking!
Apartment
Highland Falls, NY, USA
1.7k from Highlands Country Club center

Security/Safety, Air Conditioner, Fireplace/Heating, Parking, Balcony/Terrace, Guest Services, Internet

2 Bedrooms6 Guests
8.5

Very Good

2 reviews

$310
Average price / night
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Luxury home near West Point
Luxury home near West Point
House
Highland Falls, NY, 10928, United States
2.0k from Highlands Country Club center

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

10.0

Exceptional

2 reviews

$231
Average price / night
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Fabulous 3bdrm Home With Parking
Fabulous 3bdrm Home With Parking
House
Highland Falls, NY, USA
1.7k from Highlands Country Club center

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

1 Bedroom8 Guests
New to Booking
$359
Average price / night
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Walk to WP Gate and Free Parking
Walk to WP Gate and Free Parking
Apartment
Highland Falls, NY, USA
1.7k from Highlands Country Club center

Security/Safety, Air Conditioner, Parking, Internet, Pet Friendly, Child Friendly

1 Bedroom6 Guests
New to Booking
$295
Average price / night
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Luxury Townhouse Near West Point
Luxury Townhouse Near West Point
House
Highland Falls, NY, 10928, United States
2.0k from Highlands Country Club center

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

New to Booking
$323
Average price / night
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Updated Home with Patio Half Mile to West Point
Updated Home with Patio Half Mile to West Point
House
Highland Falls, NY, USA
1.9k from Highlands Country Club center

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

3 Bedrooms6 Guests
7.5

Good

2 reviews

$295
Average price / night
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West Point Mountain House
West Point Mountain House
House
West Point, NY, 10928, United States
2.7k from Highlands Country Club center

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

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$906
Average price / night
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Charming Highland Falls Home Less Than 2 Mi to West Point!
Charming Highland Falls Home Less Than 2 Mi to West Point!
House
Highland Falls, NY, USA
3.0k from Highlands Country Club center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$344
Average price / night
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Charming Highland Falls Home < 2 Mi to West Point!
Charming Highland Falls Home < 2 Mi to West Point!
House
Highland Falls, NY, 10928, United States
3.0k from Highlands Country Club center

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

4 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$481
Average price / night
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Home 2 Mi to Thayer Gate at U S Military Academy
Home 2 Mi to Thayer Gate at U S Military Academy
House
Highland Falls, NY, USA
3.3k from Highlands Country Club center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$299
Average price / night
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Bear Mountain House.
Bear Mountain House.
House
Philipstown, NY, 10524, United States
5.0k from Highlands Country Club center

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

3 Bedrooms8 Guests
10.0

Exceptional

15 reviews

$736
Average price / night
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The Glabin Garrison Gem with Deck and Fire Pit!
The Glabin Garrison Gem with Deck and Fire Pit!
House
Garrison, NY, USA
4.7k from Highlands Country Club center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$580
Average price / night
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Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cottage
Fort Montgomery, NY, 10922, United States
5.6k from Highlands Country Club center

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

1 Bedroom4 Guests
9.8

Exceptional

134 reviews

$269
Average price / night
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The Farmhouse at Fort Hill
The Farmhouse at Fort Hill
House
Peekskill, NY, USA
8.7k from Highlands Country Club center

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

1 Bedroom6 Guests
New to Booking
$252
Average price / night
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Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Cottage
Putnam Valley, NY, 10537, United States
6.1k from Highlands Country Club center

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

3 Bedrooms8 Guests
9.6

Exceptional

15 reviews

$844
Average price / night
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Cape by the Lake
Cape by the Lake
House
Putnam Valley, NY, USA
8.8k from Highlands Country Club center

Internet, Air Conditioner, Child Friendly, Parking, Balcony/Terrace, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$260
Average price / night
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Sunny House on Lake Oscawana
Sunny House on Lake Oscawana
House
Putnam Valley, NY, 10579, United States
8.2k from Highlands Country Club center

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

3 Bedrooms6 Guests
10.0

Exceptional

30 reviews

$538
Average price / night
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Two King Beds and washer drier
Two King Beds and washer drier
Apartment
Peekskill, NY, USA
9.0k from Highlands Country Club center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom5 Guests
4.7

Review score

3 reviews

$98
Average price / night
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Charming Forest Getaway near West Point & Storm King
Charming Forest Getaway near West Point & Storm King
Cabin
Cornwall, NY, 12518, United States
9.3k from Highlands Country Club center

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

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$724
Average price / night
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Putnam Valley Estate 4BR - Hot Tub Fireplace
Putnam Valley Estate 4BR - Hot Tub Fireplace
Apartment
Highlands Country Club, Garrison, New York, USA
9.8k from Highlands Country Club center

Internet, Air Conditioner, Parking, Breakfast, Hot Tub, Pet Friendly, Kitchen

4 Bedrooms8 Guests
New to Booking
$630
Average price / night
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Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
House
Cortlandt Manor, NY, 10567, United States
9.3k from Highlands Country Club center

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

2 Bedrooms4 Guests
9.2

Superb

29 reviews

$324
Average price / night
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Cozy Cottage minutes to West Point
Cozy Cottage minutes to West Point
House
Cornwall-On-Hudson, NY, 12520, United States
9.7k from Highlands Country Club center

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

3 Bedrooms8 Guests
10.0

Exceptional

65 reviews

$578
Average price / night
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Historic 1800s Cornwall-On-Hudson Cottage!
Historic 1800s Cornwall-On-Hudson Cottage!
Cottage
Cornwall-On-Hudson, NY, 12520, United States
9.9k from Highlands Country Club center

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

2 Bedrooms4 Guests
10.0

Exceptional

33 reviews

$544
Average price / night
Check Availability

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 Highlands Country Club.

Highlands Country Club Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 29 verified family-friendly vacation rentals in Highlands Country Club. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Highlands Country Club vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $98 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Highlands Country Club 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 Highlands Country Club 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 Highlands Country Club often include amenities such as Child Friendly, Internet, 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.