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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Fort Montgomery vacation rentals

Property grounds

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
The price is ￥31,165
￥52,060 total
includes taxes & fees
Aug 4 - Aug 5
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Terrace/patio

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, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥19,675
￥62,968 total
includes taxes & fees
Aug 5 - Aug 6
House on the Babbling Brook- Quiet 2BR + King Bed!
TV

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 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 ￥24,956
￥42,939 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 1-bedroom retreat minutes from West Point!
Coffee/tea maker, fridge, oven, stovetop

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
9.6 out of 10, Exceptional, (23 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥18,731
￥49,123 total
includes taxes & fees
Aug 9 - Aug 10
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Coffee/tea maker, fridge, microwave, oven

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.
The price is ￥43,301
￥68,520 total
includes taxes & fees
Sep 1 - Sep 2
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
3 bedrooms, desk, iron/ironing board, travel crib

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, (18 reviews)
"Sweet abode. Cozy, clean and amazing location. The cute coffee bar was a nice bonus. Would definitely stay there again. "
United States
Danica J.
The price is ￥26,016
￥76,030 total
includes taxes & fees
Aug 17 - Aug 18
Local Artist Inspired | Walk to WestPoint + King Bed
Property grounds

7. 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 ￥28,730
￥85,588 total
includes taxes & fees
Aug 5 - Aug 6
3BR West Point Retreat-3min to Back Gate+ King Bed
Coffee/tea maker, fridge, microwave, oven

8. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 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 ￥35,415
￥66,070 total
includes taxes & fees
Aug 2 - Aug 3
Contemporary Cozy Cottage
Exterior detail

9. Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥30,854
￥82,914 total
includes taxes & fees
Aug 4 - Aug 5
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
TV

10. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (24 reviews)
"Would definitely stay here again! It was a great experience!"
United States
Jodi P.
The price is ￥47,513
￥74,157 total
includes taxes & fees
Aug 3 - Aug 4
Walk to WP Gate + Free Parking!
Exterior detail

11. West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking

West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
Highland Falls
9.4 out of 10, Exceptional, (29 reviews)
"Our stay was excellent! Extremely clean, everything we needed. Walkable to everything in town. Great communication work h Host. We will definitely be staying again. "
United States
Joelle M.
The price is ￥51,873
￥84,502 total
includes taxes & fees
Aug 2 - Aug 3
West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
Interior

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 ￥49,746
￥82,972 total
includes taxes & fees
Sep 1 - Sep 2
Lovely 3BR Home with parking-Walk to WP Gate!
Exterior detail

13. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.2 out of 10, Wonderful, (10 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is ￥49,774
￥80,845 total
includes taxes & fees
Aug 3 - Aug 4
Fabulous 3bdrm Home w/parking!
Smart TV

14. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (46 reviews)
"This apartment was perfect for what we needed! Beautifully renovated, comfortable bed, and very close to Beacon! "
United States
Abby W.
The price is ￥21,249
￥46,830 total
includes taxes & fees
Aug 3 - Aug 4
Grant - A Tranquil One Bedroom Steps from River
Outdoor spa tub

15. 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, (11 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is ￥37,304
￥72,141 total
includes taxes & fees
Aug 3 - Aug 4
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Desk, WiFi (free), bed sheets

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 ￥21,532
￥44,969 total
includes taxes & fees
Aug 6 - Aug 7
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
1 bedroom, WiFi (free)

17. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (20 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveler
The price is ￥15,809
￥17,883 total
includes taxes & fees
Sep 1 - Sep 2
2 Queen Beds | Non-Smoking, Kitchen
Cottage (2 Bedrooms) | Interior

18. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is ￥33,837
￥82,454 total
includes taxes & fees
Aug 26 - Aug 27
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Private kitchen

19. 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.
The price is ￥55,106
￥129,613 total
includes taxes & fees
Aug 2 - Aug 3
Perfect and Spacious Hudson Valley Escape!
Exterior

20. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.4 out of 10, Exceptional, (20 reviews)
"great place tostay"
United States
Anonymous traveler
The price is ￥13,427
￥15,524 total
includes taxes & fees
Aug 30 - Aug 31
2 Full Beds | 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

Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

10/10 Excellent
"Always a great and comfortable stay"
Ruby 5-night trip
Posted 4 hours ago
Hotel Nyack, a JdV by Hyatt Hotel

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 Cabin with Sauna & Firepit!: Visitors like this Fort Montgomery vacation home rental. It offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave.

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 popular places like Woodbury Common Premium Outlets and LEGOLAND® New York.

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.