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
A bright bedroom features a spacious bed with crisp linens and a patterned rug. Two windows allow natural light to fill the room, complemented by neutral wall tones. A bedside table holds decorative items, and a potted plant adds a touch of greenery.
Flat in Cornwall-on-Hudson
4.94 out of 5 average rating, 152 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
A spacious living area features a black leather sofa and an orange ottoman, complemented by a large potted palm. Bright light enters through the open door, enhancing the warm wood flooring and inviting atmosphere.
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
The exterior of a two-story house is presented against a colorful sunset sky, with hues of pink and orange blending together. A well-maintained lawn extends in front, while steps lead to the entrance, framed by tall trees and utility lines.
Guest suite in Highland Falls
5 out of 5 average rating, 65 reviews

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

The neighborhood is so quiet w/ beautiful views everywhere you look. It's a private suite, w/ private entrance & bathroom, microwave, toaster oven, mini-fridge, & of course, a coffee maker! Extra living space w/ a couch, desk & smart TV. Work out in the morning or watch TV at night. Only ~1/2 mile to West Point, so Main Street (food/drink) & Thayer Gate are in walking distance. Perfect for visiting anyone or attending an event at West Point. Quaint towns, restaurants, hiking in all directions

Top guest favourite
Guest suite in Cornwall
5 out of 5 average rating, 24 reviews

Suite Element Cabin Studio near West Point

Private woodland studio suite in Cornwall, NY with a private entrance, queen bed, WiFi, Smart TV, kitchenette (no sink or stove), patio fireplace, and seasonal treats. Located about 5 miles from West Point, 4 miles from Storm King Art Center, 10 miles from Bear Mountain, and 12 miles from Woodbury Commons. Owner lives onsite with two rescue dogs; barking and normal household sounds may occur. HVAC is host controlled. Well and septic system. Seasonal decor may be extensive.

Top guest favourite
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.
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 collage showcases the inviting exterior of the home, adorned with bunting and an American flag. Interior images display a cozy living area with comfortable seating, a well-furnished bedroom featuring blue accents, a dining space with a vintage cabinet, and a modern kitchen equipped with stainless-steel appliances.
Home in Highland Falls
5 out of 5 average rating, 50 reviews

West Point-Themed | 3BR • 2BA Near Thayer Gate

Book 4 nights and get the 5th night free! Our West Point-themed home was created specifically for Academy families who want a comfortable, private place to gather and celebrate together. Why families love staying here: • close to Thayer Gate, Main Street • 3 queen bedrooms and 2 full bathrooms • Gathering areas with games and 2 TVs • Blackstone grilling and covered deck • Thoughtful touches from a Grad Mom who understands how special these visits are

Top guest favourite
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, 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
The living room features a combination of a black sofa and a light gray couch, adorned with red accent pillows. A wooden coffee table is positioned in the center, and light from a nearby window illuminates the space, complemented by a ceiling fan and wall-mounted television.
Home in Highland Falls
4.82 out of 5 average rating, 132 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, 282 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.

Top guest favourite
Large triangular windows provide a view of the snowy landscape outside, allowing natural light to fill the space. The wood-paneled walls and ceiling create a warm ambiance, while a minimalist chandelier hangs above, adding a touch of modern design.
Guest suite in Marlboro
4.97 out of 5 average rating, 291 reviews

Viridian House

This space offers a romantic getaway for couples looking to enjoy the scenic Hudson Valley. If you are traveling solo, this cozy space is a private oasis for relaxation and leisure. Centered in the heart of Marlboro wine country, this space is right in the middle of several local wineries, breweries, farms, restaurants, and is just a short drive to the Shawangunk Mountains.

Top guest favourite
A spacious living area features a light-colored sofa with decorative cushions. A wooden coffee table sits in front, accompanied by two stylish dining chairs at a small table. Natural light fills the room through large windows, enhancing the welcoming atmosphere.
Flat in Cold Spring
4.97 out of 5 average rating, 113 reviews

Charming Village Base. Walk to Restaurants & Shops

Charming 1 BR apartment in the heart of Cold Spring. Centrally located in walking distance to restaurants and shops as well as hiking trails. About 15 min walk from Cold Spring train station. Ideally located in a Town Home in the village of Cold Spring with a private entrance.

Top guest favourite
A mid-century octagonal house is surrounded by lush greenery, featuring large glass windows that offer generous natural light. A wooden deck extends from the entry, framed by a black railing. The serene hilltop location provides a peaceful retreat in nature.
Home in New Windsor
4.92 out of 5 average rating, 145 reviews

View House

Magnificent views from this fully renovated octagonal, mid-century glass house on secluded hilltop site. Views of and close access to Storm King Art Center, Schunnemunk State Park, Black Rock Forest. 60 mi from Manhattan, Town of Cornwall, NY. Perfect getaway from the city.

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 £38 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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