Holiday houses in Highland Falls

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Top-rated holiday rentals in Highland Falls

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in Cortlandt

4.99 out of 5 average rating, 160 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

24–31 Oct

$240 NZD per night

Guest favourite

Home in Highland Falls

4.95 out of 5 average rating, 176 reviews

Luxury home near West Point

Fully furnished luxury townhouse right outside the gate of West Point, Bear Mountain and commuting distance to NYC. The Unit is SPACIOUS, BRIGHT, OPEN, AIRY with Ample STORAGE, HARDWOOD floors on First level, fully carpeted on 2nd level with Central Air. Master Bedroom-En-Suite, Two Additional Good-Size Bedrooms with Huge Closets and Washer/Dryer On 2nd Floor. Beautiful Tiled Kitchen with SS Appliances: Refrigerator, Dishwasher, Stove. 2 assigned parking spots. Level Backyard.

6–13 Nov

$886 NZD per night

Guest favourite

Apartment in Highland Falls

5.0 out of 5 average rating, 35 reviews

Lovely 2nd FL Apt Walking Distance to West Point!

Welcome To The Heart Of West Point. Beautifully Furnished Apartment. Located Steps Away from West Point. Walking Distance to Restaurants, & The Best Landmarks The Town Has To Offer. We Are Minutes Away From Hiking,Swimming, Fishing, & Much More! We are Ideally Located Near Bear Mountain State Park, Woodbury Commons & More! Apartment Includes 2 Full Size Bed, 1 Roll out Twin Bed. Comfortable Couches, Smart Tv, Wifi, & Much More. NO Parties. Family Living on 1st Floor Apartment.

28 Jan – 4 Feb

$372 NZD per night

Guest favourite

Condo in Highland Falls

4.96 out of 5 average rating, 85 reviews

❤️😍 Cozy studio apartment in quiet neighborhood 🥰❤️

Newly renovated basement space in a very quiet secluded neighborhood with a full kitchen, full size bathroom, Fast WiFi, Smart TV, Separate parking, walking distance to Hudson River, Main Street, Bear Mountain State Park, West Point Military Academy and several adventurous hiking trails. For those who like to shop we are located only 20 minutes to the Woodbury Commons and only a 45 minute drive to NYC. Also Stuart International Airport is only a short drive from here.

24–31 Jan

$295 NZD per night

Guest favourite

Apartment in New Windsor

4.95 out of 5 average rating, 118 reviews

Private/Spacious Studio. Guest Loyalty Program

LOYALTY PROGRAM for repeat bookings. $30 off of your second night stay ((dbl occ rates and extra guest fees apply) OR a 3rd guest stays free with your one night stay. Discount will be applied upon your inquiry. - Perfect location for your West Point visit. - SKAC -Woodbury Common Sleeps up to six guests comfortably. Safe/secure - Perfect for single travelers Parking at door for several vehicles Coffee/Tea/Keurig Close to restaurants, NYS Thruway, Routes 9W

1–8 Dec

$216 NZD per night

Guest favourite

Home in Highland Falls

4.99 out of 5 average rating, 142 reviews

Spacious, bright 5 bedroom house near West Point

Newly renovated 5 bedroom house located 4.3 miles from the Thayer Gate at historic West Point Military Academy. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park and many historic sites.Woodbury Commons premium outlets are 20 minute drive. The house is comfortable with many upgrades- full oven and microwave, large fridge/freezer, USB ports .Come and see an Army game - and relax here afterwards!

19–26 Jul

$772 NZD per night

Guest favourite

Guest suite in Haverstraw

4.95 out of 5 average rating, 298 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

12–19 Dec

$146 NZD per night

Guest favourite

Loft in Cornwall

4.86 out of 5 average rating, 395 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and flat screen Roku TV with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have their own parking space, a private first-floor entrance, full bathroom, patio, BBQ and fire pit!

28 Nov – 5 Dec

$171 NZD per night

Guest favourite

Guesthouse in Peekskill

4.94 out of 5 average rating, 212 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

9–16 Nov

$243 NZD per night

Guest favourite

Farm stay in Fort Montgomery

4.97 out of 5 average rating, 149 reviews

Secluded overlook cottage near West Point

This quaint little house trailer is located on a secluded horse farm in the beautiful Hudson Valley only 50 minutes from NYC and less than 10 minutes from West Pt. Situated on a mountain top, this private little space is a nature lovers paradise. Come, recline on the new outdoor deck, relax by the fire pit and hike/explore the forest trails right out the front door.

1–8 Aug

$452 NZD per night

Guest favourite

Home in Highland Falls

4.97 out of 5 average rating, 72 reviews

Bear Mountain, Westpoint, & Hikers Retreat

The Fort @Fort Montgomery, Westpoint/Bear Mountain New to the rental market! This recently renovated 900 Square foot single story home located 5 miles/7 mins from West Point Military Academy and 3 miles/ 3min from Bear Mountain is the ideal spot for friends and family to convene for a weekend visit in the Hudson Valley.

6–13 Sep

$332 NZD per night

Guest favourite

Apartment in Highland Falls

4.84 out of 5 average rating, 101 reviews

Cozy 1-bedroom retreat minutes from West Point!

Enjoy easy access to everything from this perfectly located home base. Explore the beautiful Hudson Valley, shop the outlets at Woodbury Commons or cheer for your favorite team at Army home games! You will be on a quiet street in the quaint town of Highland Falls the perfect place for work or play.

30 Sep – 7 Oct

$210 NZD per night