West Point holiday rentals

We found 565 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in West Point that are perfect for your trip. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as parking and air conditioning. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – West Point

Showing deals for:25 Dec - 1 Jan

Sit together outside, enjoy fresh Hudson Valley air, share stories and memories
Whip up delicious meals in the spacious, bright kitchen with ample counter space
View of valley and lush evergreens. Queen bed. Spacious closet
Comfortably seats 8 and also doubles as a large board game table.
Exceptional
(40 reviews)

Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz

Highland

8% off
AU$8,341
for 7 nights, 1 home
AU$1,192 per night
includes taxes & fees
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
Interior
Private kitchen
Exterior detail
Room
Exceptional
(9 reviews)

West Point Family Retreat, 5 min walk to Thayer!

Highland Falls

7% off
AU$6,678
for 7 nights, 1 home
AU$954 per night
includes taxes & fees
West Point Family Retreat, 5 min walk to Thayer!
Hallway with pocket doors on main floor
View of the dining room
Walk way to back yard from side of the house
Original mahogany wood work and French Chandliers though out the house
Exceptional
(17 reviews)

Stunning historic Victorian house in Newburgh. Pet friendly

Newburgh

21% off
AU$8,363
for 7 nights, 1 home
AU$1,195 per night
includes taxes & fees
Stunning historic Victorian house in Newburgh. Pet friendly
Property grounds
Exterior
Interior
Living area
Exceptional
(13 reviews)

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

8% off
AU$1,980
for 7 nights, 1 home
AU$283 per night
includes taxes & fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Private kitchen
Dining
Room
Living area
Exceptional
(14 reviews)

Cozy House 3 Blocks From West Pt

Highland Falls

7% off
AU$6,091
for 7 nights, 1 home
AU$870 per night
includes taxes & fees
Cozy House 3 Blocks From West Pt
Outdoor dining
Living area
Private kitchen
Pool
Exceptional
(16 reviews)

The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC

Harriman

12% off
AU$10,612
for 7 nights, 1 home
AU$1,516 per night
includes taxes & fees
The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
Dining
Main house. Apt is downstairs to the left.
Private entrance to apt.
Private kitchen
Exceptional
(22 reviews)

Lower level unit in Spectacular Log Home Estate

Marlboro

12% off
AU$2,158
for 7 nights, 1 apartment
AU$308 per night
includes taxes & fees
Lower level unit in Spectacular Log Home Estate
Private kitchen
Living area
Interior
Pool
Exceptional
(24 reviews)

6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED

Carmel

8% off
AU$13,124
for 7 nights, 1 home
AU$1,875 per night
includes taxes & fees
6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED
Dining
Property grounds
Private kitchen
Interior
Exceptional
(7 reviews)

A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley

Holmes

8% off
AU$3,968
for 7 nights, 1 home
AU$567 per night
includes taxes & fees
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Exterior
Family room
Chef’s Kitchen
Primary BR
Exceptional
(21 reviews)

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Carmel

12% off
AU$6,898
for 7 nights, 1 home
AU$985 per night
includes taxes & fees
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Dining
Property grounds
Outdoor dining
Living area
Exceptional
(9 reviews)

Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm.

Marlboro

11% off
AU$1,959
for 7 nights, 1 home
AU$280 per night
includes taxes & fees
Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm.
Interior
Interior
Interior
Interior
Exceptional
(5 reviews)

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie

6% off
AU$3,873
for 7 nights, 1 home
AU$553 per night
includes taxes & fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Memorable sunsets
Covered lakeside gazebo
Kitchen
View of kitchen from living room
Exceptional
(45 reviews)

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Newburgh

8% off
AU$4,760
for 7 nights, 1 home
AU$680 per night
includes taxes & fees
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Room
Living area
Dining
Outdoor dining
Exceptional
(29 reviews)

Hudson River Retreat

Newburgh

8% off
AU$2,242
for 7 nights, 1 apartment
AU$320 per night
includes taxes & fees
Hudson River Retreat
Dining
Outdoor spa tub
Room
Exterior
Exceptional
(15 reviews)

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

Cornwall

12% off
AU$5,155
for 7 nights, 1 home
AU$736 per night
includes taxes & fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Winter beauty
Breathtaking View, Situated on Orange Lake
Front of house. Lake in back.
Through the front door to spectacular lake beauty
Exceptional
(330 reviews)

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Newburgh

8% off
AU$5,751
for 7 nights, 1 home
AU$822 per night
includes taxes & fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Dining
Interior
Room
Outdoor dining
Exceptional
(23 reviews)

Peekskill Carriage House Downtown Studio

Peekskill

8% off
AU$2,161
for 7 nights, 1 home
AU$309 per night
includes taxes & fees
Peekskill Carriage House Downtown Studio

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting culturally rich West Point

Enjoy the area's culture, history and cathedral with a rental holiday home in West Point. This city's university setting, football games and wildlife draw many visitors. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around West Point

Are you hoping to discover things to do during your stay? Venture out of your cosy holiday rental and experience everything that West Point has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • West Point Golf Course (2.1 mi / 3.4 km)
  • Putnam County Golf Course (10.2 mi / 16.5 km)
  • Brotherhood Winery (11.1 mi / 17.8 km)
  • SplashDown Beach (11.1 mi / 17.9 km)
  • Ice Time Sports Complex (12 mi / 19.3 km)
  • Benmarl Vineyards and Winery (14 mi / 22.5 km)

Exploring the natural landscape of West Point

Whether you're looking for adventure or just want to appreciate the scenery, West Point is a great place to spend some time outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Boscobel House and Gardens (1.8 mi / 2.9 km)
  • Little Stony Point Park (2.5 mi / 4 km)
  • Storm King State Park (2.9 mi / 4.7 km)
  • Hudson Highlands State Park (3.4 mi / 5.5 km)
  • Oscawana Lake (5.5 mi / 8.9 km)
  • Fishkill Ridge (8.1 mi / 13.1 km)

Transport to and around West Point

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 10.1 mi (16.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Danbury, CT (DXR-Danbury Municipal), which is 24.4 mi (39.3 km) away.

Frequently asked questions

What is the best area to stay in West Point when booking a holiday rental?
When considering a holiday rental in West Point, New York, the area surrounding the United States Military Academy is one of the best choices. This historic neighbourhood not only offers a unique glimpse into military life but also provides stunning views of the Hudson River. Visitors can explore the West Point Museum, which showcases the rich history of the Academy and its contributions to the United States military. Additionally, the iconic West Point Cadet Chapel, renowned for its striking architecture and beautiful stained glass, is a must-see attraction.Another appealing option is the nearby Highland Falls, which features a charming small-town atmosphere with lovely shops and eateries. This area serves as a gateway to outdoor activities, including hiking trails that lead to picturesque viewpoints overlooking the river and surrounding landscapes.
What is the most popular type of holiday rental accomodation in West Point?
In West Point, holiday houses are the most popular type of holiday rental, with several available throughout the area. These homes offer a spacious and comfortable environment, ideal for families or groups looking to enjoy the scenic surroundings. Most holiday houses come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces for relaxation.
Are there any family house rentals in West Point?
In West Point, there are several family-friendly house rentals available, making it an excellent choice for families looking to explore this historic area. Properties in the vicinity often provide spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play. Many homes also come with modern amenities such as Wi-Fi and laundry facilities, ensuring a comfortable stay.Visitors will appreciate the proximity to points of interest such as the United States Military Academy, where they can learn about the rich history of the area. Additionally, the scenic Hudson River offers opportunities for outdoor activities like hiking and picnicking, superb for family outings.
Are there pet-friendly house rentals in West Point?
In West Point, there are several pet-friendly house rentals available, making it a great choice for travellers looking to bring their furry companions along. The area offers a variety of rental options, including charming cottages and spacious homes, often equipped with amenities such as full kitchens, outdoor spaces, and comfortable living areas.West Point itself is steeped in history and natural beauty, with breathtaking views of the Hudson River and the surrounding mountains. While enjoying your stay, you can explore the picturesque West Point campus, which features lovely walking paths and green spaces where pets are welcome.
Are there any remote work holiday rentals in West Point?
In West Point, there are several remote work holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many properties come equipped with amenities tailored for remote work, such as dedicated desk areas, comfortable chairs, and reliable Wi-Fi, ensuring a productive environment for guests.The area itself is steeped in history and natural beauty, with the scenic Hudson River providing a picturesque backdrop. Visitors can explore nearby attractions, including the United States Military Academy and the stunning views from the surrounding hills. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in West Point?
In West Point, popular holiday rental amenities include balconies for enjoying the scenic views of the surrounding area, as well as coffee and tea makers to help guests start their day with a warm beverage. Many properties also feature decks or patios, providing outdoor spaces where visitors can relax and take in the fresh air. Additionally, accommodations often come equipped with desks and desk chairs, making them suitable for guests who may need to work or study during their stay.
When is the best time to visit West Point for a holiday rental?
The peak travel season in West Point spans from May to July, with June being particularly popular among visitors. This vibrant month welcomes those eager to soak up the rich history and stunning landscapes of the area. The warmer weather, typically ranging from 15 to 30 degrees Celsius, makes it an ideal time for outdoor activities like hiking along the scenic trails of the Hudson Highlands or enjoying a leisurely stroll around the iconic West Point campus.During this bustling season, you'll find a host of events and activities that cater to visitors seeking a blend of adventure and culture. The lively option, complemented by blooming gardens and picturesque views of the Hudson River, enhances the overall experience for those looking to explore the area.For those seeking a more budget-friendly option, consider planning your visit in January. While it may be the low season, this month offers a unique charm, with opportunities for winter sports and fewer crowds, allowing for a more relaxed experience as you discover the area's historical sites and natural beauty.
What are the top attractions in West Point?
In West Point, visitors can engage in the rich history and natural beauty of the area. The United States Military Academy is a prominent attraction, offering guided tours that showcase its stunning architecture and historical significance. Just a stone's throw away, the West Point Museum provides insights into military history and features a fascinating collection of artefacts.For those who appreciate scenic views, the hiking trails along the Hudson River offer breathtaking panoramas of the landscape. The nearby Bear Mountain State Park also presents opportunities for outdoor activities such as hiking, picnicking, and enjoying the views from the Perkins Memorial Tower.Additionally, the West Point Cadet Chapel, with its impressive Gothic architecture, is a must-visit for its unique design and tranquil ambiance.
Are all fees included in the West Point holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any West Point holiday homes with parking?
Stayz offers a wide selection of holiday homes in West Point with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for West Point holiday homes?
You can find great discounts on holiday homes in West Point on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my West Point holiday home booking on Stayz?
To find West Point holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in West Point?
A long-stay holiday home in West Point is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a West Point holiday home?
Book your West Point holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in West Point?
Prices for holiday homes in West Point vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in West Point to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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