Vacation rentals in Highland Falls

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Top-rated vacation rentals in Highland Falls

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Guest favorite

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

Sep 27 – Oct 4

ﺩ.ﺇ497 per night

Guest favorite

Apartment 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.

Sep 24 – Oct 1

ﺩ.ﺇ491 per night

Guest favorite

Home in Highland Falls

4.95 out of 5 average rating, 171 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.

Jan 2 – 9

ﺩ.ﺇ1,811 per night

Guest favorite

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.

Apr 11 – 18

ﺩ.ﺇ506 per night

Guest favorite

Apartment in New Windsor

4.95 out of 5 average rating, 111 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

Dec 7 – 14

ﺩ.ﺇ452 per night

Guest favorite

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!

Sep 9 – 16

ﺩ.ﺇ1,615 per night

Guest favorite

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:)

Feb 18 – 25

ﺩ.ﺇ310 per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 109 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

Nov 26 – Dec 3

ﺩ.ﺇ445 per night

Guest favorite

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!

Mar 7 – 14

ﺩ.ﺇ334 per night

Guest favorite

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

Oct 28 – Nov 4

ﺩ.ﺇ483 per night

Guest favorite

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.

Jul 21 – 28

ﺩ.ﺇ919 per night

Guest favorite

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.

Nov 11 – 18

ﺩ.ﺇ411 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Highland Falls vacation rentals

Kitchen

Wifi

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 vacation rentals in Highland Falls

Guest favorite

Home in Highland Falls

4.97 out of 5 average rating, 70 reviews

Bear Mountain, Westpoint, & Hikers Retreat

Sep 22 – 29

ﺩ.ﺇ615 per night

Guest favorite

Apartment in Highland Falls

5.0 out of 5 average rating, 35 reviews

Lovely 2nd FL Apt Walking Distance to West Point!

Feb 4 – 11

ﺩ.ﺇ731 per night

Guest favorite

Home in Highland Falls

5.0 out of 5 average rating, 49 reviews

GRAD MOM House Walk to WP King 2 Queen

Nov 12 – 19

ﺩ.ﺇ1,705 per night

Guest favorite

Guest suite in Putnam Valley

4.91 out of 5 average rating, 33 reviews

Peaceful lake and woodland retreat

Feb 9 – 16

ﺩ.ﺇ382 per night

Guest favorite

Home in Highland Falls

5.0 out of 5 average rating, 29 reviews

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

Sep 4 – 11

ﺩ.ﺇ1,535 per night

Guest favorite

Guest suite in Highland Falls

5.0 out of 5 average rating, 45 reviews

Quiet, Cozy, Private Suite ~1/2 mile to West Point

May 17 – 24

ﺩ.ﺇ876 per night

Guest favorite

Home in Highland Falls

5.0 out of 5 average rating, 67 reviews

Cozy House 3 Blocks From West Pt

Jan 22 – 29

ﺩ.ﺇ1,383 per night

Guest favorite

Guest suite in Fort Montgomery

4.99 out of 5 average rating, 94 reviews

West Point/Bear Mountain/Hudson Valley Getaway

Jul 24 – 31

ﺩ.ﺇ671 per night

Show all

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
2.4K reviews
Nightly prices starting at
ﺩ.ﺇ184 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 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.
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 wifi, over 30 homes with air conditioning, 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 apartment rentals in Highland Falls have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Highland Falls. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Highland Falls

Top-rated vacation rentals in Highland Falls

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Highland Falls vacation rentals

Stay near Highland Falls's top sights

Other great vacation rentals in Highland Falls

Home in Highland Falls

Apartment in Highland Falls

Home in Highland Falls

Guest suite in Putnam Valley

Home in Highland Falls

Guest suite in Highland Falls

Home in Highland Falls

Guest suite in Fort Montgomery

Quick stats about vacation rentals in Highland Falls

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Highland Falls?

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

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

Are there family-friendly vacation rentals in Highland Falls?

Do house rentals in Highland Falls have wifi?

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

Do house rentals in Highland Falls have a bbq area?

Do apartment rentals in Highland Falls have air conditioning?

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