Top Winter Vacations - Vacation Rentals in Fort Montgomery

Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point! From US $1,057
         

Charming Highland Falls Home Less Than 2 Mi to West Point! From US $344
         

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10.0 (1 Review)
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Updated Home w/Patio Half Mile to West Point From US $367
         

Bear Mountain House. From US $661
         

10.0 (14 Reviews)
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Luxury Places to Stay in Fort Montgomery

Over 59+ Luxury Places to Stay in or Near Fort Montgomery
West Point Mountain House From US $937
         

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West Point Family Retreat, 5 min walk to Thayer! From US $554
         

Modern Farmhouse Walking Distance to West Point From US $537
         

9.4 (10 Reviews)
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Charming 4 bedroom home close to West Point From US $509
         

Top-Rated Vacation Rentals with a Pool in Fort Montgomery

Over 5+ Top-Rated Vacation Rentals with a Pool in or Near Fort Montgomery
Holiday Inn Express West Point by IHG From US $127
         

9.2 (216 Reviews)
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Overlook Lodge at Bear Mountain From US $113
         

8.4 (1004 Reviews)
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Overlook Lodge and Stone Cottages at Bear Mountain From US $179
         

8.0 (249 Reviews)
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Pet-Friendly Vacation Rentals in Fort Montgomery

Over 14+ Pet-Friendly Vacation Rentals in or Near Fort Montgomery
Beautiful First Flr, 2-Bedroom Apt w/Free Parking From US $272
         

10.0 (5 Reviews)
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Luxury Townhouse Near West Point From US $410
         

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Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi From US $355
         

Walk to WP Gate + Free Parking! From US $302
         

9.8 (20 Reviews)
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Discover Nature’s Glory! Perfect Family Home From US $297
         

8.4 (5 Reviews)
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Highland Falls home on West Point Fence-line From US $483
         

10.0 (14 Reviews)
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Large Vacation Homes & Villas in Fort Montgomery

Over 4+ Large Vacation Homes & Villas in or Near Fort Montgomery
Walk 2mins to West Point Academy! Free private parking WiFi From US $293
         

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8.6 (5 Reviews)
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Less than a mile from West Point! Lovely Cape Cod alongside a rolling brook. From US $959
         

Restored Historic Home 1 Mile from West Point From US $573
         

10.0 (11 Reviews)
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Wheelchair Accessible Vacation Homes in Fort Montgomery

Over 1+ Wheelchair Accessible Vacation Homes in or Near Fort Montgomery

Fort Montgomery Varoom and Airbnb Places to Stay Under $200

Over 10+ Fort Montgomery Varoom and Airbnb Places to Stay Under $200
Cozy 1-bedroom retreat minutes from West Point! From US $191
         

West Point Motel From US $113
         

8.6 (657 Reviews)
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Local Artist Inspired | Walk to WestPoint + King Bed From US $168
         

Cozy 1-bedroom retreat minutes from West Point! From US $116
         

8.8 (3 Reviews)
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Bear Mountain Bridge Motel Regular Room From US $140
         

9.4 (35 Reviews)
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Nature Lovers' Sanctuary Yet Close to Amenities From US $125
         

Instantly Bookable Vacation Homes in Fort Montgomery

Over 12+ Instantly Bookable Vacation Homes in or Near Fort Montgomery
Quiet Apt with Coffee Bar, 1/2 Mile to West Point! From US $275
         

Cozy House 3 Blocks From West Pt From US $385
         

9.8 (11 Reviews)
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Fabulous 3bdrm Home w/parking! From US $312
         

9.0 (4 Reviews)
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About Fort Montgomery Vacation Rentals

With more than 68 Fort Montgomery vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Topwintervacations and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Fort Montgomery.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Topwintervacations Fort Montgomery, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Fort Montgomery. Places to stay near Fort Montgomery are 804.77 ft² on average, with prices averaging $383 a night.

Topwintervacations makes it easy and safe to find and compare vacation rentals in Fort Montgomery with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Fort Montgomery

Type Count
Vacation Homes 40
Holiday Apartments 17
Hotels with Suites 8
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Fort Montgomery

Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Fort Montgomery.

Weather in Fort Montgomery

View the weather forecast for Fort Montgomery before booking your Fort Montgomery Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Fort Montgomery, NY