A mountainous landscape with a bridge in the distance.

Fort Montgomery Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Fort Montgomery holiday 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, (144 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AU$459
includes taxes & fees
10 Sept - 11 Sept
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

2. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (11 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AU$545
includes taxes & fees
10 Sept - 11 Sept
House on the Babbling Brook- Quiet 2BR + King Bed!

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 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 AU$267
includes taxes & fees
10 Sept - 11 Sept
Cozy 1-bedroom retreat minutes from West Point!
A blue house with a white porch, a welcome sign, and a mailbox.

4. 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 AU$645
includes taxes & fees
10 Sept - 11 Sept
3BR West Point Retreat-3min to Back Gate+ King Bed
A hallway with a wooden door, a black table with a sign, and large green plants.

5. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"We had a great stay at Joseph’s home. The property was very clean, spacious, and well prepared for guests. My work team and I felt comfortable right away, and the house had everything we needed for both a productive and relaxing stay.Joseph was always kind, professional, and quick to respond, which made a big difference. I would recommend this property without hesitation."
United States
ROHID S.
The price is AU$587
includes taxes & fees
10 Sept - 11 Sept
3BR Near West Point | Coffee Bar | Sleeps 6
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

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

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is AU$641
includes taxes & fees
29 Sept - 30 Sept
Local Artist Inspired | Walk to WestPoint + King Bed
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

7. 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 AU$315
includes taxes & fees
10 Sept - 11 Sept
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A wooden coffee table with two decorative planters in a living room.

8. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
The price is AU$610
includes taxes & fees
22 Sept - 23 Sept
Walk to WP Gate + Free Parking!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

9. 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 AU$623
includes taxes & fees
29 Sept - 30 Sept
Fabulous 3bdrm Home w/parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

10. 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 AU$631
includes taxes & fees
10 Sept - 11 Sept
Lovely 3BR Home with parking-Walk to WP Gate!
The exterior of Highland Falls Library with a white facade, two wooden benches in front, and a sign above the entrance.

11. Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi

Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
Highland Falls
9.6 out of 10, Exceptional, (36 reviews)
"Good location and had a great stay!"
United States
James M.
The price is AU$802
includes taxes & fees
10 Sept - 11 Sept
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
A deck with Adirondack chairs, a fire pit, and a grill.

12. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (13 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is AU$570
includes taxes & fees
22 Sept - 23 Sept
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

13. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (40 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is AU$611
includes taxes & fees
30 Sept - 1 Oct
Contemporary Cozy Cottage
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

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

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"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 AU$692
includes taxes & fees
22 Sept - 23 Sept
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A wooden cabin with large windows, a wooden bench, and a view of the forest.

15. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is AU$315
includes taxes & fees
14 Sept - 15 Sept
Harriman Outdoor Center - Mountain Laurel Cabin
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

16. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
The price is AU$406
includes taxes & fees
10 Sept - 11 Sept
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A living room with a fireplace, a painting, shelves with decorative items, and a television.

17. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (48 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
The price is AU$412
includes taxes & fees
14 Sept - 15 Sept
Grant - A Tranquil One Bedroom Steps from River
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!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
The price is AU$967
includes taxes & fees
13 Sept - 14 Sept
Bright Cornwall-on-hudson Vacation Rental!

19. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
8.6 out of 10, Excellent, (24 reviews)
"Worst hotel experience I have ever had. Grounds were unkept. No one was at the front desk when I first arrived. Waited 20 minutes for someone to arrive and had to leave for dinner. Came back to find out that they were overbooked."
United States
Glenn
The price is AU$128
includes taxes & fees
30 Sept - 1 Oct
2 Queen Beds | Non-Smoking, Kitchen
A brick building with a sign reading 'Lobby' in front.

20. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Nice place to stay"
United States
Anonymous traveller
The price is AU$131
includes taxes & fees
5 Oct - 6 Oct
1 Queen Bed | Non-Smoking, Kitchen
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

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"An excellent location for the purpose of our visit - clean and quiet with a very helpful staff."
mary 2-night trip
Posted 3 hours ago
Crowne Plaza Suffern - Mahwah by IHG

Find out more about Fort Montgomery

Everything you need to know about Fort Montgomery holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fort Montgomery holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Fort Montgomery holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fort Montgomery holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fort Montgomery holiday rentals we have selected for you start as low as AU$131 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Fort Montgomery rentals

At Expedia, we put the best Fort Montgomery holiday 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 holiday.

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 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Fort Montgomery offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and kitchenware, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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. In the wider area, you’ll find Bear Mountain State Park and Woodbury Common Premium Outlets.

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.