Vacation Rentals in Fort Montgomery, NY: Compare 10+ Sites & Save

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72 Best Vacation Rentals in Fort Montgomery (Starting from $242)

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
2.1k from Fort Montgomery 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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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
0.9k from Fort Montgomery 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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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
2.4k from Fort Montgomery 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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Family friendly 4-bedroom home, 2 miles from West Point, loaded with amenities
Family friendly 4-bedroom home, 2 miles from West Point, loaded with amenities
House
Highland Falls, NY, 10928, United States
2.0k from Fort Montgomery center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$569
Average price / night
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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
4.2k from Fort Montgomery 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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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
4.2k from Fort Montgomery 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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Bear Mountain House.
Bear Mountain House.
House
Philipstown, NY, 10524, United States
2.1k from Fort Montgomery 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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Beautiful 2BR Apartment-, Walk To West Point, Free Parking!
Beautiful 2BR Apartment-, Walk To West Point, Free Parking!
Apartment
Highland Falls, NY, USA
4.2k from Fort Montgomery 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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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
2.4k from Fort Montgomery 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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Walk to WP Gate and Free Parking
Walk to WP Gate and Free Parking
Apartment
Highland Falls, NY, USA
4.2k from Fort Montgomery 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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Historic home at West Point on Main Street. 1 mile from Thayer Gate!
Historic home at West Point on Main Street. 1 mile from Thayer Gate!
House
Highland Falls, NY, 10928, United States
3.4k from Fort Montgomery center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, No Smoking, TV

4 Bedrooms10 Guests
10.0

Exceptional

9 reviews

$1185
Average price / night
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Fabulous 3bdrm Home With Parking
Fabulous 3bdrm Home With Parking
House
Highland Falls, NY, USA
4.3k from Fort Montgomery 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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Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point!
Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point!
House
Garrison, NY, 10524, United States
3.5k from Fort Montgomery center

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

3 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$1153
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
4.3k from Fort Montgomery 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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The Mountain Muse Private Artsy Studio
The Mountain Muse Private Artsy Studio
Apartment
Highland Falls, NY, 10928, United States
3.6k from Fort Montgomery center

Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, TV

1 Bedroom4 Guests
New to Booking
$242
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
6.0k from Fort Montgomery 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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Walk to West Point from this 2-bedroom charmer
Walk to West Point from this 2-bedroom charmer
House
Highland Falls, NY, 10928, United States
3.7k from Fort Montgomery center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms4 Guests
9.8

Exceptional

13 reviews

$439
Average price / night
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The Farmhouse at Fort Hill
The Farmhouse at Fort Hill
House
Peekskill, NY, USA
7.1k from Fort Montgomery 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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5 BR West Point Family Compound- Sleeps 10!
5 BR West Point Family Compound- Sleeps 10!
House
Highland Falls, NY, 10928, United States
3.8k from Fort Montgomery center

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

5 Bedrooms10 Guests
New to Booking
$682
Average price / night
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Peekskill Guesthouse
Peekskill Guesthouse
House
Fort Montgomery, New York, USA
7.2k from Fort Montgomery center

Parking, Laundry, Kitchen, Internet, Air Conditioner

1 Bedroom1 Guest
New to Booking
$300
Average price / night
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Walk to WP Gate + Free Parking!
Walk to WP Gate + Free Parking!
Apartment
Highland Falls, NY, 10928, United States
4.2k from Fort Montgomery center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
9.8

Exceptional

22 reviews

$287
Average price / night
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Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Apartment
Highland Falls, NY, 10928, United States
4.2k from Fort Montgomery center

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

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$257
Average price / night
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Cozy 3bedroom home in Highland Falls, only a five-minute walk from West Point NY
Cozy 3bedroom home in Highland Falls, only a five-minute walk from West Point NY
House
Highland Falls, NY, 10928, United States
4.2k from Fort Montgomery center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$434
Average price / night
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Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
Apartment
Highland Falls, NY, 10928, United States
4.2k from Fort Montgomery center

AC, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
9.8

Exceptional

35 reviews

$368
Average price / night
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West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
Apartment
Highland Falls, NY, 10928, United States
4.2k from Fort Montgomery center

AC, Crib, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, TV

2 Bedrooms6 Guests
9.6

Exceptional

27 reviews

$349
Average price / night
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Modern West Point House near USMA - 3 bed, 2 bath with Hot tub & Fire pit!
Modern West Point House near USMA - 3 bed, 2 bath with Hot tub & Fire pit!
House
Highland Falls, NY, 10928, United States
4.2k from Fort Montgomery center

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

3 Bedrooms6 Guests
10.0

Exceptional

18 reviews

$840
Average price / night
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Lovely 3BR Home with parking-Walk to WP Gate!
Lovely 3BR Home with parking-Walk to WP Gate!
House
Highland Falls, NY, 10928, United States
4.3k from Fort Montgomery center

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

3 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$316
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 Vacation Rentals in Fort Montgomery.

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Frequently Asked Questions

You can explore 72 verified vacation rentals in Fort Montgomery. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Fort Montgomery vary depending on the season, property size, and location. Rates typically start from around $242 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Fort Montgomery include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Fort Montgomery welcome pets. Currently, 20 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Fort Montgomery often include amenities such as Fireplace/Heating, Internet, and Bedding/Linens. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.