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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (149 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥31,033
￥52,210 total
includes taxes & fees
Oct 27 - Oct 28
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Living area

2. 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 ￥18,283
￥34,561 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 1-bedroom retreat minutes from West Point!
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
9.2 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 ￥18,040
￥45,434 total
includes taxes & fees
Oct 25 - Oct 26
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

4. 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, (14 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 ￥19,591
￥63,953 total
includes taxes & fees
Oct 27 - Oct 28
House on the Babbling Brook- Quiet 2BR + King Bed!
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 ￥22,459
￥68,050 total
includes taxes & fees
Oct 26 - Oct 27
Local Artist Inspired | Walk to WestPoint + King Bed
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is ￥35,705
￥65,722 total
includes taxes & fees
Oct 26 - Oct 27
Hudson Valley/West Point Retreat w/ parking!
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

7. 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 ￥27,609
￥78,234 total
includes taxes & fees
Nov 1 - Nov 2
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A blue house with a white porch, a welcome sign, and a mailbox.

8. 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 ￥24,629
￥80,304 total
includes taxes & fees
Oct 26 - Oct 27
3BR West Point Retreat-3min to Back Gate+ King Bed
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 ￥31,131
￥53,447 total
includes taxes & fees
Nov 17 - Nov 18
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

10. 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 ￥36,237
￥63,601 total
includes taxes & fees
Nov 17 - Nov 18
Fabulous 3bdrm Home w/parking!
A wooden coffee table with two decorative planters in a living room.

11. 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 ￥34,919
￥58,373 total
includes taxes & fees
Nov 17 - Nov 18
Walk to WP Gate + Free Parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

12. 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 ￥33,602
￥61,873 total
includes taxes & fees
Nov 17 - Nov 18
Lovely 3BR Home with parking-Walk to WP Gate!
A hallway with a wooden door, a black table with a sign, and large green plants.

13. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"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 ￥23,666
￥72,690 total
includes taxes & fees
Oct 25 - Oct 26
3BR Near West Point | Coffee Bar | Sleeps 6
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, (41 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 ￥35,264
￥66,326 total
includes taxes & fees
Oct 25 - Oct 26
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 ￥35,923
￥70,601 total
includes taxes & fees
Nov 2 - Nov 3
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Step up to a warm welcome - our charming entryway, complete with a hanging birdhouse, sets the tone for a peaceful stay.

16. 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, (25 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥49,635
￥108,366 total
includes taxes & fees
Oct 31 - Nov 1
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.

17. 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 ￥38,151
￥85,221 total
includes taxes & fees
Nov 4 - Nov 5
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A living room with a fireplace, a painting, shelves with decorative items, and a television.

18. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (52 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 ￥21,159
￥45,035 total
includes taxes & fees
Nov 9 - Nov 10
Grant - A Tranquil One Bedroom Steps from River
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.

19. '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 ￥26,143
￥50,693 total
includes taxes & fees
Nov 1 - Nov 2
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

20. 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 ￥58,199
￥109,550 total
includes taxes & fees
Nov 22 - Nov 23
Bright Cornwall-on-hudson Vacation Rental!
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

Inn on the Hudson

Inn on the Hudson

8/10 Good
"Bathroom needed updating, tub peeling, ceiling peeling. Bed comfortable, location perfect, parking easy. Ice machine was not where welcome book indicated."
Deborah 1-night trip
Posted 16 hours ago
Inn on the Hudson

Find out more about Fort Montgomery

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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.