Holiday houses in Highland Falls

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Top-rated holiday rentals in Highland Falls

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Guest favourite

Cottage in Cortlandt

4.99 out of 5 average rating, 159 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

1–8 Aug

$255 NZD per night

Superhost

Apartment in Philipstown

4.88 out of 5 average rating, 186 reviews

Foxglove Farm

Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

6–13 Aug

$246 NZD per night

Superhost

Apartment in Peekskill

4.84 out of 5 average rating, 114 reviews

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

27 Sep – 4 Oct

$243 NZD per night

Guest favourite

Home in Highland Falls

4.95 out of 5 average rating, 169 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.

5–12 Jan

$891 NZD per night

Guest favourite

Condo in Highland Falls

4.96 out of 5 average rating, 82 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.

12–19 Sep

$297 NZD per night

Guest favourite

Home in Highland Falls

4.99 out of 5 average rating, 141 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!

27 Jul – 3 Aug

$758 NZD per night

Guest favourite

Guest suite in Haverstraw

4.95 out of 5 average rating, 292 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:)

14–21 Feb

$147 NZD per night

Guest favourite

Loft in Cornwall

4.86 out of 5 average rating, 390 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 Oct – 4 Nov

$172 NZD per night

Guest favourite

Guesthouse in Peekskill

4.94 out of 5 average rating, 206 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

28 Oct – 4 Nov

$243 NZD per night

Guest favourite

Farm stay in Fort Montgomery

4.97 out of 5 average rating, 148 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 Jul

$455 NZD per night

Guest favourite

Apartment in Highland Falls

4.84 out of 5 average rating, 98 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.

4–11 Sep

$212 NZD per night

Guest favourite

Apartment in New Windsor

4.95 out of 5 average rating, 110 reviews

Quiet/Private/Spacious Studio. Balcony. Parking.

-Perfect location for West Point visitors. Quiet. Private. Bring the family! Sleeps up to six guests comfortably. -Visit SKAC -Shop Woodbury Common Safe/secure - Perfect for single travelers Parking at door for several vehicles Coffee/Tea/Keurig Close to restaurants, NYS Thruway, Routes 9W

3–10 Oct

$218 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Highland Falls holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Highland Falls's top sights

The Thayer Hotel15 locals recommend

West Point Academy60 locals recommend

The Park11 locals recommend

Andy's11 locals recommend

American Burrito3 locals recommend

Schade's6 locals recommend

Other great holiday rentals in Highland Falls

Guest favourite

Home in Highland Falls

4.97 out of 5 average rating, 69 reviews

Bear Mountain, Westpoint, & Hikers Retreat

26 Aug – 2 Sep

$320 NZD per night

Guest favourite

Apartment in Highland Falls

5.0 out of 5 average rating, 34 reviews

Lovely 2nd FL Apt Walking Distance to West Point!

17–24 Nov

$392 NZD per night

Guest favourite

Home in Highland Falls

5.0 out of 5 average rating, 48 reviews

GRAD MOM House Walk to WP King 2 Queen

12–19 Sep

$872 NZD per night

Guest favourite

Home in Highland Falls

5.0 out of 5 average rating, 18 reviews

Highland Falls Home - 1/2 Mile to West Point

2–9 Mar

$528 NZD per night

Guest favourite

Guest suite in Fort Montgomery

4.99 out of 5 average rating, 94 reviews

West Point/Bear Mountain/Hudson Valley Getaway

2–9 May

$360 NZD per night

Guest favourite

Home in Highland Falls

5.0 out of 5 average rating, 66 reviews

Cozy House 3 Blocks From West Pt

4–11 Nov

$752 NZD per night

Guest favourite

Home in Highland Falls

5.0 out of 5 average rating, 28 reviews

Luxe West Point Retreat: 3BR/2BA w/HotTub, FirePit

8–15 Feb

$927 NZD per night

Guest favourite

Home in Highland Falls

4.96 out of 5 average rating, 91 reviews

Enjoy Walking Privileges! WestPoint Farmhouse

10–17 Sep

$833 NZD per night

Show all

Quick stats about holiday rentals in Highland Falls

Total rentals	50 properties
Rentals with dedicated workspaces	30 properties have a dedicated workspace
Pet-friendly rentals	10 properties allow pets
Family-friendly rentals	30 properties are a good fit for families
Total number of reviews	2.4K reviews
Nightly prices starting at	$85 NZD before taxes and fees

Holiday houses in Highland Falls

Top-rated holiday rentals in Highland Falls

Cottage in Cortlandt

Apartment in Philipstown

Apartment in Peekskill

Home in Highland Falls

Condo in Highland Falls

Home in Highland Falls

Guest suite in Haverstraw

Loft in Cornwall

Guesthouse in Peekskill

Farm stay in Fort Montgomery

Apartment in Highland Falls

Apartment in New Windsor

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Highland Falls holiday rentals

Stay near Highland Falls's top sights

Other great holiday rentals in Highland Falls

Home in Highland Falls

Apartment in Highland Falls

Home in Highland Falls

Home in Highland Falls

Guest suite in Fort Montgomery

Home in Highland Falls

Home in Highland Falls

Home in Highland Falls

Quick stats about holiday rentals in Highland Falls

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore