Fort Montgomery Vacation Rentals from AED 287: Search Short-Term Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

Fort Montgomery

Jasmine

AED 1,115 total

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Highland Falls

AED 1,747 total

includes taxes & fees

8 Dec - 9 Dec

A hallway with a wooden door, a black table with a sign, and large green plants.

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

Highland Falls

mario b.

AED 1,539 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Highland Falls

Andrew L.

AED 1,076 total

includes taxes & fees

15 Nov - 16 Nov

A house with a white front door, a small porch with a white railing, and a window with a green curtain.

5. Fabulous 3bdrm Home w/parking!

Highland Falls

Beth M.

AED 1,324 total

includes taxes & fees

8 Dec - 9 Dec

A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

6. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Highland Falls

Maria L.

AED 1,169 total

includes taxes & fees

17 Nov - 18 Nov

A wooden coffee table with two decorative planters in a living room.

7. Walk to WP Gate + Free Parking!

Highland Falls

Jerell T.

AED 1,224 total

includes taxes & fees

8 Dec - 9 Dec

A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

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

Highland Falls

Morgan S.

AED 1,522 total

includes taxes & fees

15 Nov - 16 Nov

A room with a wooden floor, a white door with a number, and a window with blinds.

9. Lovely 3BR Home with parking-Walk to WP Gate!

Highland Falls

Briana T.

AED 1,303 total

includes taxes & fees

8 Dec - 9 Dec

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

Highland Falls

Zack C.

AED 733 total

includes taxes & fees

8 Dec - 9 Dec

A blue house with a white porch, a welcome sign, and a mailbox.

11. 3BR West Point Retreat-3min to Back Gate+ King Bed

Highland Falls

Christine T.

A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

12. Mountain-View 2BR Steps from Thayer Gate

Highland Falls

AED 1,238 total

includes taxes & fees

15 Nov - 16 Nov

A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

13. Perfect 2BR with Free Parking! Walk to West Point!

Highland Falls

AED 1,184 total

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

14. Contemporary Cozy Cottage

Lake Peekskill

Heather M.

AED 1,420 total

includes taxes & fees

16 Nov - 17 Nov

A deck with Adirondack chairs, a fire pit, and a grill.

15. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

Cornwall

Elisabeth

AED 1,610 total

includes taxes & fees

16 Nov - 17 Nov

A spacious living area with a black leather sofa, a coffee table, a ceiling fan, and a blue cabinet.

16. Spacious 4-bedroom house in northern Westchester with sweeping views

Montrose

AED 2,260 total

includes taxes & fees

13 Nov - 14 Nov

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

Lake Peekskill

Karen W.

AED 2,451 total

includes taxes & fees

16 Nov - 17 Nov

A living room with a fireplace, a blue armchair, a wooden coffee table, and a sofa with cushions.

18. Bright Cornwall-On-Hudson Vacation Rental!

Cornwall-On-Hudson

Betty B.

AED 2,495 total

includes taxes & fees

22 Nov - 23 Nov

A living room with a fireplace, a painting, shelves with decorative items, and a television.

19. Grant - A Tranquil One Bedroom Steps from River

Newburgh

Martha Z.

View all properties

Find vacation rentals that suit your style

Top Fort Montgomery Hotel Reviews

A large, multi-story stone building with a prominent arched entrance and multiple windows.

Overlook Lodge at Bear Mountain

Bear Mountain

10/10 Excellent

Giuseppe

A buffet with various food items, including omelets and baked goods, served in metal containers.

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Peekskill

10/10 Excellent

David Allen

A lobby with a grand chandelier, two large arched windows, and a central fireplace with a portrait above it.

The Thayer Hotel at West Point

West Point

10/10 Excellent

Amy

A hotel entrance with stone pillars, a covered walkway, and a bench.

Sleep Inn & Suites Monroe - Woodbury

Monroe

10/10 Excellent

Lisyani

A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.

Homewood Suites Stewart Airport

New Windsor

10/10 Excellent

Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.

Anonymous traveler

An outdoor patio area with a stone fire pit, seating, and a Marriott sign in the background.

SpringHill Suites by Marriott Fishkill

Fishkill

10/10 Excellent

MICHELLE

A Holiday Inn Express hotel with a covered entrance, a parking lot, and a well-lit facade.

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

10/10 Excellent

Jeris

A hotel room with a green sofa, a small table, a bed with a headboard, a desk with a lamp, and a framed picture on the wall.

Quality Inn & Suites Fishkill South near I-84

Fishkill

10/10 Excellent

Lynn

A patio area with outdoor seating and a fire pit, surrounded by buildings with a brick facade and a covered seating area.

Best Western Fishkill Inn & Suites

Fishkill

10/10 Excellent

MHD Amar

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.

Fort Montgomery Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Fort Montgomery vacation rentals

1. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

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

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

5. Fabulous 3bdrm Home w/parking!

6. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

7. Walk to WP Gate + Free Parking!

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

9. Lovely 3BR Home with parking-Walk to WP Gate!

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

11. 3BR West Point Retreat-3min to Back Gate+ King Bed

12. Mountain-View 2BR Steps from Thayer Gate

13. Perfect 2BR with Free Parking! Walk to West Point!

14. Contemporary Cozy Cottage

15. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

16. Spacious 4-bedroom house in northern Westchester with sweeping views

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

18. Bright Cornwall-On-Hudson Vacation Rental!

19. Grant - A Tranquil One Bedroom Steps from River

Find vacation rentals that suit your style

Top Fort Montgomery Hotel Reviews

Overlook Lodge at Bear Mountain

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Fort Montgomery?

What are some of the best vacation rentals that Fort Montgomery has to offer?

What’s there to see and do in Fort Montgomery?

What’s a vacation rental in Fort Montgomery like?