Vacation rentals in Highland Falls

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Top-rated vacation rentals in Highland Falls

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Top guest favorite
The exterior of a contemporary two-story home is showcased, featuring a combination of gray and wood paneling. The property is situated on a landscaped slope adorned with planters. A set of stone steps leads up to the entrance, framed by greenery and a cloudy sky above.
Home in Highland Falls
5 out of 5 average rating, 83 reviews

Modern Usma Home, Walk to West Point. Hot Tub!

Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers.

Superhost
A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.
Loft in Mountainville
4.84 out of 5 average rating, 593 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, 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 two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Superhost
A light-filled space features a well-equipped kitchen with modern appliances and a minimalist design. The wooden staircase, adorned with potted plants, leads to a cozy upper area. Natural light streams in through the window, illuminating the warm wooden flooring and vibrant area rug.
Apartment in Newburgh
4.84 out of 5 average rating, 335 reviews

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Guest favorite
A cozy living area is showcased with two accent chairs, one in a warm terracotta tone and another in vibrant red, featuring a playful design. The wooden floor complements the inviting atmosphere, while framed artwork adorns the walls, adding visual interest to the space.
Guest suite in Chester
4.96 out of 5 average rating, 348 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, French door shower, and a kitchenette with sunny breakfast nook. It's freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Top guest favorite
A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.
Guesthouse in Cold Spring
4.99 out of 5 average rating, 189 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

Top guest favorite
A two-story home is showcased with light-colored siding and vibrant red shutters. The entrance is marked by a white railing and steps leading to the front door. An American flag proudly stands on a flagpole in the front yard, bordered by a white picket fence.
Condo in Highland Falls
4.97 out of 5 average rating, 115 reviews

Cozy West Point Hide Away and Cadet’s Get Away

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.

Guest favorite
A cozy studio space includes a queen bed with a light-colored coverlet. A kitchenette features essential appliances, complemented by a dining area with wooden table and black chairs. A flat-screen TV is mounted on the wall, and natural light brightens the room.
Guest suite in Mountainville
4.95 out of 5 average rating, 129 reviews

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited.

Top guest favorite
An open dining area features a wooden table surrounded by six dark chairs. A stylish light fixture hangs above, and a modern kitchen with white cabinetry and stainless steel appliances is visible in the background. Natural light filters through nearby windows.
Home in Highland Falls
4.99 out of 5 average rating, 182 reviews

Spacious, bright 5 bedroom house near West Point

Recently renovated 5 bedroom, 2 bathroom 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!

Superhost
A comfortable living area is showcased with a neutral-colored sofa and a wooden coffee table. Patterned curtains frame the windows, and a vase of flowers sits on the table. Soft lighting from a floor lamp enhances the inviting ambiance.
Apartment in Highland Falls
4.81 out of 5 average rating, 174 reviews

2nd Fl 2BR Apt Walking distance to WestPoint

I am located in a beautiful area close to all, 3 mins or less walk to the Thayer gate at West Point, also within walking distance to all local restaurants/bars in town, mins away from the bear mountain bridge where the view is spectacular of the Hudson river and more. Beautiful mountains for hikers! This is a great location for family and friends visiting anyone at Westpoint.

Top guest favorite
A charming house trailer is shown with white trim and multiple windows, surrounded by trees. An outdoor wooden deck features a grill, purple chairs, and a small pumpkin. Steps lead up to the entrance, offering access to the inviting outdoor space.
Farm stay in Fort Montgomery
4.98 out of 5 average rating, 216 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.

Guest favorite
A dining area features a light wood table surrounded by four chairs. A cozy seating arrangement is located nearby, complemented by a bookshelf filled with books and decorative items. Natural light streams through the windows, highlighting the exposed brick wall and wooden beams.
Apartment in Cold Spring
4.94 out of 5 average rating, 622 reviews

Beautiful loft space

Located in the heart of Cold Spring, NY, this beautiful architect-designed loft space is only 2 blocks away from the Metro North train stop. It features a large single bedroom, a full kitchen, a full dining table and chairs, and a sleeper sofa.

Top guest favorite
The exterior of the guest house features a light-colored facade with a shingled roof. Two garage doors are centered on the front, flanked by planters. A paved driveway leads to the entrance, which is surrounded by trees and greenery.
Bed and breakfast in Highland Falls
4.99 out of 5 average rating, 177 reviews

Riverview B&B 2 Miles to West Point

"Rosenkavalier" is a full apartment / B&B located in Highland Falls, New York on the majestic Hudson River in the Cragston sub-community, just 2 miles south of the historic US Military Academy at West Point and 45 miles north of New York City.

Popular amenities for Highland Falls vacation rentals

When is the best time to visit Highland Falls?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR4,100 ZARR3,101 ZARR3,428 ZARR4,306 ZARR4,685 ZARR4,840 ZARR3,325 ZARR3,841 ZARR3,549 ZARR4,014 ZARR4,427 ZARR4,117 ZAR
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

Quick stats about vacation rentals in Highland Falls

  • Total rentals

    60 properties

  • Nightly prices starting at

    R861 ZAR before taxes and fees

  • Total number of reviews

    3.4K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Highland Falls?

    Four-legged friends are welcome in Highland Falls. Choose from more than 20 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in apartment rentals in Highland Falls?

    Experience the best of Highland Falls with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Highland Falls have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Highland Falls. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Highland Falls?

    Yes! Work meets play with ease at over 40 vacation rentals in Highland Falls featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Highland Falls?

    Highland Falls has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Highland Falls have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Highland Falls. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Highland Falls have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Highland Falls. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Highland Falls?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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