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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (146 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥31,159
￥52,050 total
includes taxes & fees
Oct 8 - Oct 9
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
9.8 out of 10, Exceptional, (13 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is ￥19,834
￥63,827 total
includes taxes & fees
Oct 1 - Oct 2
House on the Babbling Brook- Quiet 2BR + King Bed!
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥18,102
￥48,304 total
includes taxes & fees
Oct 1 - Oct 2
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Living area

4. 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 ￥22,148
￥38,405 total
includes taxes & fees
Oct 28 - Oct 29
Cozy 1-bedroom retreat minutes from West Point!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

5. 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 ￥21,726
￥70,770 total
includes taxes & fees
Oct 6 - Oct 7
Local Artist Inspired | Walk to WestPoint + King Bed
A hallway with a wooden door, a black table with a sign, and large green plants.

6. 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 ￥19,047
￥63,051 total
includes taxes & fees
Oct 6 - Oct 7
3BR Near West Point | Coffee Bar | Sleeps 6
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 and modern with good amenities. Would stay here again. "
United States
Daniel C.
The price is ￥43,303
￥64,952 total
includes taxes & fees
Oct 28 - Oct 29
Walk to WP Gate + Free Parking!
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

8. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
The price is ￥22,195
￥67,375 total
includes taxes & fees
Oct 6 - Oct 7
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

9. 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 ￥39,171
￥60,018 total
includes taxes & fees
Oct 28 - Oct 29
Beautiful First Flr, 2-Bedroom Apt w/ Free 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 ￥26,032
￥51,723 total
includes taxes & fees
Oct 1 - Oct 2
Lovely 3BR Home with parking-Walk to WP Gate!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

11. 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 ￥35,408
￥66,057 total
includes taxes & fees
Oct 6 - Oct 7
Contemporary Cozy Cottage
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

12. 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 ￥45,287
￥70,762 total
includes taxes & fees
Oct 28 - Oct 29
Fabulous 3bdrm Home w/parking!
A living room with a fireplace, a painting, shelves with decorative items, and a television.

13. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (50 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 ￥21,250
￥44,518 total
includes taxes & fees
Oct 5 - Oct 6
Grant - A Tranquil One Bedroom Steps from River
A deck with Adirondack chairs, a fire pit, and a grill.

14. 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, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is ￥33,371
￥63,035 total
includes taxes & fees
Oct 6 - Oct 7
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
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.

15. '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, (3 reviews)
"Great stay!"
United States
Ann S.
The price is ￥23,423
￥47,312 total
includes taxes & fees
Oct 4 - Oct 5
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A wooden cabin with large windows, a wooden bench, and a view of the forest.

16. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is ￥30,845
￥35,753 total
includes taxes & fees
Oct 13 - Oct 14
Harriman Outdoor Center - Mountain Laurel Cabin
The exterior of Highland Falls Library with a white facade, two wooden benches in front, and a sign above the entrance.

17. 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 ￥78,548
￥123,265 total
includes taxes & fees
Oct 11 - Oct 12
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

18. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (9 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is ￥30,978
￥57,574 total
includes taxes & fees
Oct 1 - Oct 2
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A stone staircase leading to a house with a stone wall and a metal gate.

19. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is ￥39,353
￥62,834 total
includes taxes & fees
Oct 3 - Oct 4
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

20. 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.
The price is ￥26,256
￥54,154 total
includes taxes & fees
Oct 4 - Oct 5
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
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

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent
"Hello. Everything in this Hotel its great. Amazing Attention, cleaning everywhere. Excellent breakfast. Bedroom clean, and comfortable. Thank you Sleep Inn."
Benjamin 1-night trip
Posted 2 hours ago
Sleep Inn & Suites Monroe - Woodbury

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:

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

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.