Holiday rentals in West Point

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Top-rated holiday rentals in West Point

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

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Top guest favourite
Flat in Cornwall-on-Hudson
4.94 out of 5 average rating, 151 reviews

Quaint Apartment in Cornwall on Hudson

Looking for a weekend getaway? Come experience this centrally-located apartment in the quaint village of Cornwall-on-Hudson. Step outside to find river views, enjoy miles of hiking trails, Hudson River picnics and kayaking that start right up the road. Just minutes to West Point, the Storm King Art Center, Mount Beacon and Woodbury Commons and still in walking distance to shops, restaurants, and parks. We’re excited to make this your favorite place to stay while visiting the Hudson Valley area.

Guest favourite
The kitchenette features a compact design with white cabinets and a wooden countertop. A convection toaster oven, pots, and a sink are visible, along with various kitchenware including plates and glasses. A towel hangs nearby, providing convenience for guests.
Guest suite in Cornwall
4.94 out of 5 average rating, 166 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. We live here with kids/dogs so you may hear us moving

Guest favourite
Flat in Newburgh
4.86 out of 5 average rating, 216 reviews

Historic Stunner w/WasherDryer, Balcony, 2 bedroom

Our cozy historical 2 bedroom apartment with river views, two porches, and modern upgrades is just what you need for a delightful getaway or focused work-cation. We've preserved historical charms (hardwood floors, historical trim, retro fixtures) while adding in modern amenities (washer/dryer, dishwasher, stylish bathroom, new kitchen, electric car charger, etc!). Less than a mile from the Newburgh-Beacon Ferry launch, which connects you to Metro North Train. Note: Located on the second floor!

Top guest favourite
A well-maintained front yard features a vibrant array of flowers, including pink and yellow blooms. Neatly trimmed bushes and a white fence enhance the inviting appearance of the farmhouse. The porch is visible, providing a pleasant outdoor space that complements the lush landscaping.
Home in Highland Falls
4.97 out of 5 average rating, 121 reviews

Ultimate Walking Access to Thayer Gate USMA

Stay an extra day on us! Book 4 nights and get the 5th night free at this beautiful farmhouse. Enjoy the ultimate walking access to Thayer Gate and immerse yourself in the West Point experience. Hosted by a ‘23 Old Grad Mom, our home features a kitchen with granite counters, dining for 10, a 75” SmartTV, and a great backyard for entertaining. Relax in cold AC near the Academy. No smoking or pets. No exceptions/loss of deposit. Book your Army getaway today! No smoking or pets or loss of deposit.

Top guest favourite
An outdoor patio area features multiple reclining lounge chairs on a smooth wooden deck. A large umbrella provides shade over the seating area, while lush greenery lines the perimeter. A stylish outdoor bar and a cozy circular chair enhance the inviting space.
Home in Highland Falls
5 out of 5 average rating, 102 reviews

Modern 3BD West Point USMA House w/ HotTub!

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!

Guest favourite
Cottage in Greenwood Lake
4.98 out of 5 average rating, 382 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Top guest favourite
Flat in Highland Falls
4.97 out of 5 average rating, 121 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.

Top guest favourite
A newly renovated two-story house features dark siding and white trim, complemented by a covered front porch with railing. The American flag is displayed on one side. A paved driveway leads up to the house, surrounded by lush greenery and landscaping.
Home in Highland Falls
4.99 out of 5 average rating, 198 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!

Guest favourite
Home in Highland Falls
4.82 out of 5 average rating, 131 reviews

Lovely 3BR Home with parking-Walk to WP Gate!

Walk to West Point! Enjoy the Hudson Valley. Bring the whole family to this great place with lots of room for fun. Cozy up in our spacious living room while dinner is cooking in the fully equipped kitchen. The back deck is perfect for morning coffee, unwinding in the evening with a glass of wine or a family BBQ. You will find everything you need for work or play here in the heart of Highland Falls, New York. Looking forward to having you!

Top guest favourite
Guest suite in New Windsor
4.96 out of 5 average rating, 277 reviews

Spacious Studio/ SKAC/USMA/Morning Muffins

Private quiet setting for couples Roomy enough for friends weekend West Point parents/your cadet stays free ***Single traveler discount Welcome basket - Home-baked goodies 2 Super comfy queen beds Luxurious bathroom/heated Jacuzzi bath/seated walk in shower Desk/Wifi Private parking/entrance 42 inch tv Coffee/tea/condiments SKAC USMA Woodbury Common DIA Beacon Hiking -No cooking allowed.

Guest favourite
An open studio layout features a dining island with black chairs, a cozy couch in the corner, and a spacious bed made with neutral bedding. Decorative walls showcase intricate designs, while numerous pendant lights hang from the ceiling, illuminating the area. Large windows provide natural light.
Guest house in Peekskill
4.93 out of 5 average rating, 319 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

Top guest favourite
An open-plan living space features a light-colored sectional sofa and a dark leather coffee table. A dining area with a table and four chairs is positioned near highlighted kitchen cabinets. Warm wood flooring complements the neutral walls, enhancing the modern design of the room.
Home in New Windsor
4.96 out of 5 average rating, 145 reviews

4 Bd Paradise Gorgeous Design Close to All!

Forget your worries in this spacious and serene space. The Riley house is close to Stewart Airport, West Point, NYMA, The Storm King School and Mount Saint Mary College and all the Hudson Valley has to offer. Central to Wallkill, Patterson, and Warwick as well. Extra fees will apply for guests over 6 and pets.

Popular amenities for West Point holiday rentals

When is the best time to visit West Point?

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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in West Point?

    Four-legged friends are welcome in West Point. Choose from more than 50 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in West Point?

    Yes! Work meets play with ease at over 70 vacation rentals in West Point featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in West Point?

    West Point has more than 100 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in West Point?

    Experience the best of West Point 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 house rentals in West Point have air conditioning?

    Absolutely! We offer over 80 house rentals with air conditioning in West Point. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in West Point have wifi?

    Absolutely! We offer over 90 house rentals with wifi in West Point. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in West Point have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in West Point. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in West Point have a gym?

    Absolutely! We offer over 10 house rentals with a gym in West Point. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in West Point

  • Total holiday rentals

    Explore 140 holiday rentals in West Point

  • Nightly prices starting at

    West Point holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 8,770 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    140 of West Point holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across West Point rentals

  • 4.9 Average rating

    West Point stays are highly rated by guests – averaging 4.9 out of 5!

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