A mountainous landscape with a bridge in the distance.

Fort Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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, (141 reviews)
"We had a great stay!!"
United States
Jasmine
$284 nightly
The price is $335
Sep 1 - Sep 2
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

2. 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)
"Visiting West Point for ring weekend. Location was great and the reason we chose the place. Property itself could really use some TLC, but it met our needs. Communication with the owner was good and gaining access to the property was straightforward. Would consider staying here again just based on the close proximity to West Point."
United States
Kevin
$229 nightly
The price is $254
Sep 2 - Sep 3
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

3. 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.
$297 nightly
The price is $327
Aug 31 - Sep 1
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

4. 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.
$289 nightly
The price is $325
Aug 31 - Sep 1
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

5. 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.
$360 nightly
The price is $402
Sep 1 - Sep 2
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A wooden coffee table with two decorative planters in a living room.

6. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (25 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
$404 nightly
The price is $452
Sep 29 - Sep 30
Total with taxes and fees
Walk to WP Gate + Free Parking!
The exterior of Highland Falls Library with a white facade, two wooden benches in front, and a sign above the entrance.

7. 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.
$474 nightly
The price is $584
Aug 31 - Sep 1
Total with taxes and fees
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
A deck with Adirondack chairs, a fire pit, and a grill.

8. 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
$355 nightly
The price is $419
Aug 31 - Sep 1
Total with taxes and fees
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.

9. 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.
$400 nightly
The price is $458
Sep 28 - Sep 29
Total with taxes and fees
Contemporary Cozy Cottage

10. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (24 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$436 nightly
The price is $481
Aug 31 - Sep 1
Total with taxes and fees
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

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

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
$565 nightly
The price is $624
Sep 8 - Sep 9
Total with taxes and fees
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

12. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
$298 nightly
The price is $341
Sep 2 - Sep 3
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A wooden cabin with large windows, a wooden bench, and a view of the forest.

13. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
$224 nightly
The price is $227
Aug 31 - Sep 1
Total with taxes and fees
Harriman Outdoor Center - Mountain Laurel Cabin
A living room with a fireplace, a painting, shelves with decorative items, and a television.

14. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (47 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.
$257 nightly
The price is $291
Aug 31 - Sep 1
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A brick building with a sign reading 'Lobby' in front.

15. 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 traveler
$82 nightly
The price is $94
Sep 2 - Sep 3
Total with taxes and fees
1 Queen Bed | Non-Smoking, Kitchen
A deck with wicker furniture, a bench, and a table.

16. River Views & Deck | River Suite on Washington

River Views & Deck | River Suite on Washington
Newburgh
$361 nightly
The price is $424
Sep 2 - Sep 3
Total with taxes and fees
River Views & Deck | River Suite on Washington
A modern kitchen with grey cabinets, a central island, bar stools, and a stainless steel range hood.

17. Perfect and Spacious Hudson Valley Escape!

Perfect and Spacious Hudson Valley Escape!
Cornwall
8.0 out of 10, Very Good, (2 reviews)
"Great host, very responsive and accommodating. The house was very clean and comfortable."
United States
Joseph S.
$691 nightly
The price is $816
Sep 7 - Sep 8
Total with taxes and fees
Perfect and Spacious Hudson Valley Escape!
A wooden cabin with large windows, a wooden bench, and a view of the forest.

18. Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
$278 nightly
The price is $282
Sep 7 - Sep 8
Total with taxes and fees
Harriman Outdoor Center - Cranberry Cabin

19. Luxury Hudson Valley Retreat near West Point, Storm King & Beacon

Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
Cornwall
9.0 out of 10, Wonderful, (2 reviews)
"Great House, less than 15 mins to front gate at West Point, convenient location for visiting and enjoying activities at West Point, e.g. football games, cadet events for family members, etc. Hope to be able to stay there again on another visit to the "Rockbound Highland Home"!!! "
United States
Jeff M.
$886 nightly
The price is $1,047
Aug 31 - Sep 1
Total with taxes and fees
Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

20. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (18 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$74 nightly
The price is $83
Sep 16 - Sep 17
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"Great"
Jose 2-night trip
Posted 5 hours ago
Overlook Lodge at Bear Mountain

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Fort Montgomery in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $94 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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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?

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town: Visitors like this Fort Montgomery vacation home rental. It has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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

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.