Vacation rentals in Highland Falls

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Top-rated vacation rentals in Highland Falls

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

Guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 158 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

Aug 28 – Sep 4

$118 per night
Superhost

Apartment in Highland Falls

4.82 out of 5 average rating, 262 reviews

Stay in the Heart of West Point! Walk to Academy

Enjoy this huge private 2 bedroom apartment on Main Street in the heartbeat of Highland Falls and walk just 3 mins to the Military Academy. At this perfect West Point getaway you'll find the best hiking, boating, swimming, fishing & golf this central location has to offer with a short drive to Bear Mountain State Park and ZOO, Woodbury Commons Outlet, Storm King Art Center, Eisenhower Theater and Legoland!! Perfect place to kick back and relax after an Army football game or day of hiking!

Jul 19 – 26

$233 per night
Guest favorite

Home in Highland Falls

4.95 out of 5 average rating, 162 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.

Jul 12 – 19

$245 per night

Popular amenities for Highland Falls vacation rentals

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 vacation rentals in Highland Falls

Guest favorite

Home in Highland Falls

5.0 out of 5 average rating, 67 reviews

Bear Mountain, Westpoint, & Hikers Retreat

Jul 11 – 18

$145 per night
Guest favorite

Apartment in Highland Falls

5.0 out of 5 average rating, 34 reviews

Lovely 2nd FL Apt Walking Distance to West Point!

Sep 25 – Oct 2

$173 per night
Guest favorite

Home in Highland Falls

5.0 out of 5 average rating, 46 reviews

GRAD MOM House Walk to WP King 2 Queen

Jul 14 – 21

$384 per night
Guest favorite

Home in Highland Falls

4.96 out of 5 average rating, 54 reviews

Grad owned cozy 5 bd home right outside West Point

Jul 24 – 31

$300 per night
Guest favorite

Home in Highland Falls

5.0 out of 5 average rating, 16 reviews

Highland Falls Home - 1/2 Mile to West Point

Aug 1 – 8

$240 per night
Guest favorite

Home in Highland Falls

5.0 out of 5 average rating, 27 reviews

Modern West Point Retreat: 3BR, 2BA w/Hot Tub fire

Mar 5 – 12

$442 per night
Guest favorite

Home in Highland Falls

4.97 out of 5 average rating, 38 reviews

House on the Babbling Brook

Apr 8 – 13

$166 per night
Guest favorite

Home in Highland Falls

5.0 out of 5 average rating, 62 reviews

Cozy House 3 Blocks From West Pt

Feb 6 – 13

$412 per night
Guest favorite

Guest suite in Putnam Valley

4.9 out of 5 average rating, 30 reviews

Peaceful lake and woodland retreat

Feb 21 – 28

$91 per night
Guest favorite

Home in Highland Falls

4.96 out of 5 average rating, 48 reviews

West Point Mountain House

Sep 16 – 23

$537 per night
Guest favorite

Guest suite in Fort Montgomery

4.99 out of 5 average rating, 92 reviews

West Point/Bear Mountain/Hudson Valley Getaway

Jun 11 – 18

$165 per night
Guest favorite

Home in Highland Falls

4.96 out of 5 average rating, 90 reviews

Best Location to West Point, Beautiful Farmhouse

Jan 1 – 8

$413 per night

Quick stats about vacation 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

2.3K reviews

Nightly prices starting at

$50 before taxes and fees

Frequently Asked Questions

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

    Four-legged friends are welcome in Highland Falls. Choose from more than 10 vacation rentals for guests traveling with pets.

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

    Experience the best of Highland Falls with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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

    Yes! Work meets play with ease at over 30 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 30 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 30 house rentals with wifi in Highland Falls. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 30 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Highland Falls have a bbq area?

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

  • Do house rentals in Highland Falls have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Highland Falls. Enjoy a tailored experience with all the comforts you desire.

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