Fort Montgomery Holiday Rentals

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Our top choices for Fort Montgomery holiday rentals

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is AU$469
includes taxes & fees
18 Dec - 19 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Fishkill
9.6 out of 10, Exceptional, (49)
"Inside was very nice, outside could use some curb appeal. Enjoyed our stay "
United States
Karen K.
The price is AU$482
includes taxes & fees
10 Dec - 11 Dec
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large,Cozy,Bright Apartment, Business Themed.

Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is AU$735
includes taxes & fees
18 Dec - 19 Dec
Large,Cozy,Bright Apartment, Business Themed.

Hickory on Willow Lake

Fishkill
9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
The price is AU$863
includes taxes & fees
29 Dec - 30 Dec
Hickory on Willow Lake

Rustic Cabin in Fishkill!

Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is AU$693
includes taxes & fees
8 Jan - 9 Jan 2026
Rustic Cabin in Fishkill!

Modern penthouse suite in a restored grain tower with private roof deck.

Warwick
10.0 out of 10, Exceptional, (27)
"Wonderful stay!"
United States
Lisi M.
The price is AU$824
includes taxes & fees
10 Dec - 11 Dec
Modern penthouse suite in a restored grain tower with private roof deck.

Eaglefest time! Plus stunning winter views of Croton River Gorge, a birder haven

Croton-on-Hudson
9.6 out of 10, Exceptional, (15)
"We enjoyed our overnight stay at this quaint nicely appointed carriage house."
United States
Cathleen C.
Eaglefest time! Plus stunning winter views of Croton River Gorge, a birder haven

Cabin in the heart of the Hudson Valley, Cabin 2

Newburgh
9.4 out of 10, Exceptional, (30)
"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."
United States
Sara B.
The price is AU$306
includes taxes & fees
8 Jan - 9 Jan 2026
Cabin in the heart of the Hudson Valley, Cabin 2

Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

Greenwood Lake
9.8 out of 10, Exceptional, (8)
"Awesome place. Cozy and great communication with owners. "
United States
Dominick P.
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Warwick
9.2 out of 10, Wonderful, (7)
"Nice to have top notch bar/restaurant downstairs!"
United States
John E
The price is AU$226
includes taxes & fees
10 Dec - 11 Dec
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

3.0 star property
Carmel
10.0 out of 10, Exceptional, (3)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
The price is AU$341
includes taxes & fees
11 Dec - 12 Dec
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA

Beacon
9.6 out of 10, Exceptional, (11)
"The views from the property match the pictures and in a great accessible location "
United States
Isis J.
Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA

House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls
10.0 out of 10, Exceptional, (5)
The price is AU$659
includes taxes & fees
21 Dec - 22 Dec
House on the Babbling Brook- Quiet 2BR + King Bed!

Chestnut on Willow Lake

Fishkill
9.6 out of 10, Exceptional, (4)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is AU$1,068
includes taxes & fees
10 Dec - 11 Dec
Chestnut on Willow Lake

Red Cottage - Lakeside Property!

Fishkill
The price is AU$1,121
includes taxes & fees
10 Dec - 11 Dec
Red Cottage - Lakeside Property!

Luxury 9BR Retreat w/Pool & Hot Tub

Chester
7.0 out of 10, Good, (2)
"Pool was not open or usable but we were not interested in doing that "
United States
John D.
Luxury 9BR Retreat w/Pool & Hot Tub

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Newburgh
10.0 out of 10, Exceptional, (22)
"Great host, amazing area, perfect get away!"
United States
Gianna W.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Warwick
9.4 out of 10, Exceptional, (6)
"My girlfriend and I loved our stay here! We stayed for one night and it was perfect for what we needed. Very clean with easy self-check-in. The host was very responsive with all inquiries. Short walk to nice downtown area as well!"
United States
Jay D.
The price is AU$229
includes taxes & fees
12 Dec - 13 Dec
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Greenwood Lake
10.0 out of 10, Exceptional, (30)
"We loved the house. It was a perfect and much needed short getaway for my husband and I. We brought our little dog Lenny and he loved it too! "
United States
Chelsea D.
The price is AU$682
includes taxes & fees
10 Dec - 11 Dec
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Unicorn Studio - Historic Newburgh near Beacon + Hiking

Newburgh
10.0 out of 10, Exceptional, (4)
"Great location, 10 mins away from Beacon. Its located in a quiet neighborhood. They have everything you need."
United States
Anna L.
Unicorn Studio - Historic Newburgh near Beacon + Hiking
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

Find out more about Fort Montgomery

Everything you need to know about Fort Montgomery holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fort Montgomery holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Fort Montgomery holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fort Montgomery holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fort Montgomery holiday rentals we have selected for you start as low as AU$226 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Fort Montgomery rentals

At Expedia, we put the best Fort Montgomery holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Fort Montgomery?

Yes, there are holiday rentals close to the most popular sights in Fort Montgomery, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Fort Montgomery has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Fort Montgomery offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and a coffee maker, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Blue Mountain Reservation. In the wider area, you’ll find Bear Mountain State Park and Monteverde at Oldstone.

What’s a holiday rental in Fort Montgomery like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Fort Montgomery. Holiday rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip.