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Fort Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Fort Montgomery vacation rentals

A house with a view of a bridge and mountains.

1. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (150 reviews)
"We had a great stay!!"
United States
Jasmine
The price is CA $280
CA $429 total
includes taxes & fees
Nov 16 - Nov 17
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

2. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is CA $232
CA $443 total
includes taxes & fees
Nov 11 - Nov 12
Hudson Valley/West Point Retreat w/ parking!
A hallway with a wooden door, a black table with a sign, and large green plants.

3. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
9.6 out of 10, Exceptional, (4 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
The price is CA $165
CA $574 total
includes taxes & fees
Nov 12 - Nov 13
3BR Near West Point | Coffee Bar | Sleeps 6
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

4. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is CA $201
CA $456 total
includes taxes & fees
Nov 11 - Nov 12
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

5. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is CA $218
CA $413 total
includes taxes & fees
Nov 11 - Nov 12
Fabulous 3bdrm Home w/parking!
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

6. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is CA $194
CA $352 total
includes taxes & fees
Nov 11 - Nov 12
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A wooden coffee table with two decorative planters in a living room.

7. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean, modern, functional, comfortable. Great stay"
United States
Jerell T.
The price is CA $218
CA $383 total
includes taxes & fees
Nov 11 - Nov 12
Walk to WP Gate + Free Parking!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

8. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.6 out of 10, Exceptional, (21 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is CA $186
CA $597 total
includes taxes & fees
Nov 11 - Nov 12
Local Artist Inspired | Walk to WestPoint + King Bed
A room with a wooden floor, a white door with a number, and a window with blinds.

9. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is CA $218
CA $424 total
includes taxes & fees
Nov 11 - Nov 12
Lovely 3BR Home with parking-Walk to WP Gate!
Living area

10. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is CA $146
CA $272 total
includes taxes & fees
Nov 11 - Nov 12
Cozy 1-bedroom retreat minutes from West Point!
A blue house with a white porch, a welcome sign, and a mailbox.

11. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is CA $184
CA $647 total
includes taxes & fees
Nov 11 - Nov 12
3BR West Point Retreat-3min to Back Gate+ King Bed
A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

12. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
The price is CA $181
CA $352 total
includes taxes & fees
Nov 11 - Nov 12
Mountain-View 2BR Steps from Thayer Gate
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

13. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is CA $201
CA $377 total
includes taxes & fees
Nov 11 - Nov 12
Perfect 2BR with Free Parking! Walk to West Point!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

14. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (43 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is CA $318
CA $566 total
includes taxes & fees
Nov 11 - Nov 12
Contemporary Cozy Cottage
A deck with Adirondack chairs, a fire pit, and a grill.

15. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is CA $321
CA $619 total
includes taxes & fees
Nov 11 - Nov 12
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A spacious living area with a black leather sofa, a coffee table, a ceiling fan, and a blue cabinet.

16. Spacious 4-bedroom house in northern Westchester with sweeping views

Spacious 4-bedroom house in northern Westchester with sweeping views
Montrose
The price is CA $699
CA $869 total
includes taxes & fees
Nov 11 - Nov 12
Spacious 4-bedroom house in northern Westchester with sweeping views
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

17. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
8.0 out of 10, Very good, (3 reviews)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
The price is CA $468
CA $883 total
includes taxes & fees
Nov 16 - Nov 17
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

18. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (35 reviews)
"Very comfortable house and great location."
United States
Betty B.
The price is CA $434
CA $960 total
includes taxes & fees
Nov 22 - Nov 23
Bright Cornwall-On-Hudson Vacation Rental!
A living room with a fireplace, a painting, shelves with decorative items, and a television.

19. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (53 reviews)
"Beautiful little apartment, walking to shops and easy parking"
United States
Martha Z.
The price is CA $280
CA $508 total
includes taxes & fees
Nov 11 - Nov 12
Grant - A Tranquil One Bedroom Steps from River
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Fort Montgomery Hotel Reviews

A buffet with various food items, including omelets and baked goods, served in metal containers.
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
Peekskill

10/10 Excellent

We enjoyed our stay very much. It was lovely.
Canada
Blair
Reviewed November 6, 2025
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Find out more about Fort Montgomery

Everything you need to know about Fort Montgomery vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Fort Montgomery vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fort Montgomery vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Fort Montgomery vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Fort Montgomery. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fort Montgomery vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fort Montgomery vacation rentals we have selected for you start as low as CA $111 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Fort Montgomery rentals

At Expedia, we put the best Fort Montgomery vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Fort Montgomery rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fort Montgomery vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fort Montgomery. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Fort Montgomery?

Yes, we offer vacation rentals close to the most popular points of interest in Fort Montgomery, or you can go with a more remote option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the mountain landscape in Fort Montgomery. Make sure you have time to check out the shopping and riverfront during your trip.

What are some of the best vacation rentals that Fort Montgomery has to offer?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: Visitors like this Fort Montgomery vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Fort Montgomery?

Enjoy the area's cultural attractions such as United States Military Academy, or get outdoors into nature at a spot like Boscobel House and Gardens. Other places in town to visit include Bear Mountain State Park and Fort Montgomery State Historic Site.

What’s a vacation rental in Fort Montgomery like?

Vacation rentals are private properties you can stay in for a couple of days or more in Fort Montgomery. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a small group gathering.