A mountainous landscape with a bridge in the distance.

Fort Montgomery Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Fort Montgomery holiday rentals

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 HK$1,553
HK$2,474 total
includes taxes & fees
17 Nov - 18 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is HK$2,285
HK$3,730 total
includes taxes & fees
8 Dec - 9 Dec
Hudson Valley/West Point Retreat w/ parking!

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 HK$941
HK$3,183 total
includes taxes & fees
12 Nov - 13 Nov
3BR Near West Point | Coffee Bar | Sleeps 6

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 HK$918
HK$2,298 total
includes taxes & fees
15 Nov - 16 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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 HK$1,656
HK$2,827 total
includes taxes & fees
8 Dec - 9 Dec
Fabulous 3bdrm Home w/parking!

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 HK$1,142
HK$2,023 total
includes taxes & fees
12 Nov - 13 Nov
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

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 HK$1,208
HK$2,109 total
includes taxes & fees
12 Nov - 13 Nov
Walk to WP Gate + Free Parking!

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 HK$937
HK$3,178 total
includes taxes & fees
12 Nov - 13 Nov
Local Artist Inspired | Walk to WestPoint + King Bed

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 HK$1,557
HK$2,782 total
includes taxes & fees
8 Dec - 9 Dec
Lovely 3BR Home with parking-Walk to WP Gate!

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 HK$808
HK$1,512 total
includes taxes & fees
12 Nov - 13 Nov
Cozy 1-bedroom retreat minutes from West Point!

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 HK$1,012
HK$3,555 total
includes taxes & fees
12 Nov - 13 Nov
3BR West Point Retreat-3min to Back Gate+ King Bed

12. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
The price is HK$1,573
HK$2,644 total
includes taxes & fees
15 Nov - 16 Nov
Mountain-View 2BR Steps from Thayer Gate

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

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is HK$1,572
HK$2,527 total
includes taxes & fees
16 Nov - 17 Nov
Perfect 2BR with Free Parking! Walk to West Point!

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 HK$1,765
HK$3,032 total
includes taxes & fees
22 Nov - 23 Nov
Contemporary Cozy Cottage

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 HK$1,914
HK$3,438 total
includes taxes & fees
16 Nov - 17 Nov
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

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 HK$3,883
HK$4,827 total
includes taxes & fees
13 Nov - 14 Nov
Spacious 4-bedroom house in northern Westchester with sweeping views

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)
"This home was just as advertised and perfect for a girls weekend getaway. It was clean, cozy and a picture-perfect fall view. Would highly recommend."
United States
Karen W.
The price is HK$2,891
HK$5,235 total
includes taxes & fees
16 Nov - 17 Nov
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

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 HK$2,408
HK$5,327 total
includes taxes & fees
22 Nov - 23 Nov
Bright Cornwall-On-Hudson Vacation Rental!

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 HK$1,553
HK$2,805 total
includes taxes & fees
12 Nov - 13 Nov
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Fort Montgomery Hotel Reviews

Find out more about Fort Montgomery

Search for holiday rentals in Fort Montgomery on Expedia! You can easily find your home rentals, villas, holiday apartments in Fort Montgomery using one of the methods below:

  • View our selection of featured holiday rentals in Fort Montgomery
  • Use the map to find apartments and other holiday homes in the Fort Montgomery neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Fort Montgomery while they last

Look no further and take a look at our great range of rental properties in Fort Montgomery!

Frequently asked questions

Are there holiday rentals in Fort Montgomery?

Yes, there are holiday rentals close to the most popular sights in Fort Montgomery, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Fort Montgomery has to offer?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Fort Montgomery is located on a lake, and has a patio, a garden and a BBQ 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 holiday rental in Fort Montgomery like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Fort Montgomery. Holiday rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip.