Holiday rentals 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, 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

3–10 Aug

₹12,074 per night

Guest favourite

Flat in Philipstown

4.88 out of 5 average rating, 187 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.

24 Sep – 1 Oct

₹11,125 per night

Guest favourite

Apartment 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.

6–13 Feb

₹12,825 per night

Guest favourite

Flat in New Windsor

4.95 out of 5 average rating, 112 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

3–10 Nov

₹10,250 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

₹33,327 per night

Guest favourite

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 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:)

18–25 Apr

₹7,039 per night

Guest favourite

Guest house in Mahopac

4.96 out of 5 average rating, 110 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

28 Oct – 4 Nov

₹10,279 per night

Guest favourite

Loft in Cornwall

4.86 out of 5 average rating, 393 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!

24–31 Oct

₹7,583 per night

Guest favourite

Guest house 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

₹10,945 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.

26 Aug – 2 Sep

₹20,849 per night

Guest favourite

Flat 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.

16–23 Apr

₹9,317 per night

Guest favourite

Flat in Nelsonville

4.86 out of 5 average rating, 117 reviews

Wooded stream side Retreat

Small basement apartment nestled in the village of Cold Spring, within walking distance to Main Street (10 minutes) and train (15-20 min). Apartment borders a wooded stream that leads to the old foundry and the Hudson River. Plenty of hiking nearby. Ample parking in driveway. Privacy.

10–17 Feb

₹9,503 per night