New Windsor holiday homes

We found 260 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in New Windsor that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – New Windsor

Showing deals for:18 Dec - 25 Dec

Room
Private kitchen
Interior
Living area
Exceptional
(9 reviews)

West Point Family Retreat, 5 min walk to Thayer!

Highland Falls

8% off
NZ$7,691
for 7 nights, 1 home
NZ$1,099 per night
includes taxes & fees
West Point Family Retreat, 5 min walk to Thayer!
Walk way to back yard from side of the house
View of the dining room
Original mahogany wood work and French Chandliers though out the house
Hallway with pocket doors on main floor
Exceptional
(17 reviews)

Stunning historic Victorian house in Newburgh. Pet friendly

Newburgh

20% off
NZ$10,149
for 7 nights, 1 home
NZ$1,450 per night
includes taxes & fees
Stunning historic Victorian house in Newburgh. Pet friendly
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
NZ$2,677
for 7 nights, 1 apartment
NZ$382 per night
includes taxes & fees
Lower level unit in Spectacular Log Home Estate
Exterior
Property grounds
Living area
Outdoor dining
Exceptional
(9 reviews)

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

Marlboro

12% off
NZ$2,339
for 7 nights, 1 home
NZ$334 per night
includes taxes & fees
Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm.
Memorable sunsets
Covered lakeside gazebo
Kitchen
Breakfast nook
Exceptional
(44 reviews)

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

Newburgh

7% off
NZ$5,997
for 7 nights, 1 home
NZ$857 per night
includes taxes & fees
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Room
Outdoor spa tub
Exterior
Private kitchen
Exceptional
(14 reviews)

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

Cornwall

11% off
NZ$5,703
for 7 nights, 1 home
NZ$815 per night
includes taxes & fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Front of house. Lake in back.
Breathtaking View, Situated on Orange Lake
Open floor kitchen, LR, and DR, with panoramic view of lake.
Winter beauty
Exceptional
(330 reviews)

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

Newburgh

8% off
NZ$6,993
for 7 nights, 1 home
NZ$999 per night
includes taxes & fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Interior
Living area
Dining
Room
Exceptional
(29 reviews)

Hudson River Retreat

Newburgh

8% off
NZ$2,710
for 7 nights, 1 apartment
NZ$387 per night
includes taxes & fees
Hudson River Retreat

  • 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

The lakeside setting of New Windsor is ready to explore

Enjoy the art galleries and other features of New Windsor. Travellers especially like the shopping, restaurants and lake in this welcoming and scenic city. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around New Windsor

Do you want to find attractions to see while you're in the area? Venture out of your holiday home and experience everything that makes New Windsor a fun spot to go on holiday. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Ice Time Sports Complex (5.4 mi / 8.6 km)
  • Brotherhood Winery (7.8 mi / 12.6 km)
  • SplashDown Beach (7.8 mi / 12.6 km)
  • Benmarl Vineyards and Winery (8.3 mi / 13.4 km)
  • Putnam County Golf Course (15 mi / 24.2 km)
  • LEGOLAND® New York (16.5 mi / 26.6 km)

Exploring the natural landscape of New Windsor

Whether you're an adventurous traveller or just want to take in the scenery, New Windsor is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Algonquin Park (3.6 mi / 5.8 km)
  • Storm King State Park (4 mi / 6.5 km)
  • Hudson Highlands State Park (4.3 mi / 7 km)
  • Little Stony Point Park (4.6 mi / 7.4 km)
  • Boscobel House and Gardens (6.2 mi / 10 km)
  • Bowdoin Park (9.5 mi / 15.3 km)

Travelling to and around New Windsor

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 3.6 mi (5.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Danbury, CT (DXR-Danbury Municipal), which is 28.8 mi (46.3 km) away.

Frequently asked questions

What is the best area to stay in New Windsor when booking a holiday rental?
When considering a holiday rental in New Windsor, New York, the area around the waterfront is particularly appealing. This neighbourhood offers a charming blend of scenic views and convenient access to local attractions. Just a short distance away, you'll find the beautiful Storm King Art Centre, which features an impressive collection of large-scale sculptures set amidst stunning landscapes. Additionally, the nearby Hudson Highlands State Park is great for those who enjoy hiking and outdoor activities, providing breathtaking views of the Hudson River.In terms of accommodation options, New Windsor boasts a variety of properties, ranging from cosy cottages to more spacious homes, suiting different group sizes and preferences.
Where are the best New Windsor ski resort rentals?
For ski resort rentals near New Windsor, the best option is to look towards the nearby Catskill Mountains, particularly around the town of Tannersville and Hunter Mountain. These areas are approximately a one to two-hour drive from New Windsor and offer a range of accommodations suitable for winter sports enthusiasts.In Tannersville, visitors can find cosy chalets and spacious cabins that often come with amenities such as modern kitchens, fireplaces, and hot tubs, superb for unwinding after a day on the slopes. Many properties in this area provide easy access to ski lifts, as well as proximity to local shops and restaurants, enhancing the convenience for travellers.Hunter Mountain, renowned for its excellent skiing conditions, offers a variety of lodgings, including ski-in/ski-out condos and larger homes that can accommodate groups or families. These rentals typically feature essentials such as ski storage, comfortable living areas, and sometimes even communal amenities like pools or game rooms.For those looking to enjoy more than just skiing, the surrounding Catskills region is rich in natural beauty, with opportunities for snowshoeing and winter hiking in the nearby state parks.
What is the most popular type of holiday rental accomodation in New Windsor?
In New Windsor, holiday houses are the most popular type of holiday rental, with about 18 available in the area. These homes typically provide spacious living environments, including multiple bedrooms and fully equipped kitchens, making them ideal for families or larger groups. Additionally, many of these properties feature outdoor spaces such as gardens or patios, superb for relaxing after a day of exploring nearby attractions like the Hudson River or the scenic landscapes of the surrounding region.
Are there any family house rentals in New Windsor?
In New Windsor, there are several family-friendly house rentals available, suiting those seeking a comfortable stay. The neighbourhood is well-situated, providing easy access to local attractions such as the scenic Hudson River and the picturesque Storm King Art Centre, which is superb for outdoor exploration and cultural experiences. Many of these homes feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces for children to play.Visitors can expect amenities such as Wi-Fi, air conditioning, and sometimes even backyards with patios or decks for relaxation. The area is also close to parks and recreational facilities, making it easy for families to enjoy outdoor activities together.
Can I rent a holiday home with a pool or hot tub in New Windsor?
In New Windsor, there are several holiday homes available for rent that feature pools and hot tubs. This charming town, located near the beautiful Hudson River, offers a range of properties suited for relaxation and leisure. Many of these rentals come with amenities such as private swimming pools, inviting hot tubs, and spacious outdoor areas, superb for enjoying the scenic surroundings.Travellers can also expect fully equipped kitchens, comfortable living spaces, and sometimes additional features like barbecue grills and outdoor dining areas.
Are there pet-friendly house rentals in New Windsor?
In New Windsor, there are several pet-friendly house rentals available for those looking to enjoy a comfortable stay. Many of these properties feature spacious layouts, fully equipped kitchens, and outdoor spaces, making them ideal for families and pet owners. The area offers a mix of modern amenities, including Wi-Fi, air conditioning, and laundry facilities, ensuring a convenient experience for all guests.While staying in New Windsor, pet owners can take advantage of nearby parks such as the scenic Algonquin Park, which provides ample walking trails and open spaces for pets to explore. Additionally, the Hudson River waterfront is not far away, offering picturesque views and opportunities for leisurely strolls.
Are there any remote work holiday rentals in New Windsor?
In New Windsor, there are approximately 20 remote work holiday rentals available, making it a great choice for those looking to blend work and leisure. Many of these properties come equipped with amenities tailored for productivity, such as high-speed Wi-Fi, dedicated workspaces with desks and chairs, and even printers available for use.The area is conveniently located near the scenic Hudson River, providing opportunities for outdoor breaks and relaxation after work hours. Local attractions include historical sites and parks, superb for unwinding in nature. Additionally, the nearby town of Newburgh offers a charming waterfront, restaurants, and shops, enhancing the overall experience for remote workers looking to enjoy both their professional and personal time. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in New Windsor?
In New Windsor, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals conveniently. Many properties also offer onsite parking, which is particularly beneficial for those travelling by car. For those needing to work or stay connected, rentals often feature dedicated desk spaces along with comfortable desk chairs. Additionally, some accommodations may provide blenders, suiting guests who enjoy making smoothies or other blended drinks during their stay.
When is the best time to visit New Windsor for a holiday rental?
The best time to visit New Windsor for a holiday rental is during the peak season, which runs from June to August. This vibrant period attracts many holidaymakers keen to explore the beautiful Hudson Valley, where outdoor activities abound, from hiking to cycling along scenic trails. July, in particular, stands out as the most popular month, offering warm temperatures and a lively option superb for family gatherings and social events.During the summer, you can expect pleasant weather, with temperatures typically ranging from 20 to 30 degrees Celsius. This creates ideal conditions for enjoying the area's rich history, with nearby attractions like the historic Washington's Headquarters and the stunning views from the Storm King Art Centre. The close proximity of these sites makes it convenient for sightseeing and outdoor adventures.For those seeking a more budget-friendly experience, consider visiting in December. While this month may be less crowded, it offers its own charm with the festive holiday season. Enjoy the picturesque winter landscapes and the tranquillity that comes when the summer crowds have dispersed.Ultimately, the best time to visit New Windsor depends on whether you prefer the energetic summer vibe filled with activities or the peacefulness of winter, where you can embrace the beauty of the season.
What are the top attractions in New Windsor?
In New Windsor, visitors can explore several attractions that highlight the area's historical and natural beauty. One top site is the Washington's Headquarters State Historic Site, where George Washington set up his headquarters during the Revolutionary War, providing rich insight into American history. Nearby, the New Windsor Cantonment State Historic Site offers further exploration of military history with reconstructed barracks and exhibits.For those who enjoy the outdoors, the scenic views along the Hudson River can be appreciated at parks such as the scenic Hudson River Waterfront Park, which features walking trails and picnic areas. Additionally, the nearby Storm King Art Centre, located just a short drive away, showcases large-scale outdoor sculptures set against a backdrop of rolling hills, making it a superb day trip for art enthusiasts.
Are all fees included in the New Windsor holiday homes prices shown on Bookabach?
Bookabach 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 New Windsor holiday homes with parking?
Bookabach offers a wide selection of holiday homes in New Windsor 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 New Windsor holiday homes?
You can find great discounts on holiday homes in New Windsor on Bookabach, 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 New Windsor holiday home booking on Bookabach?
To find New Windsor holiday rentals with free cancellation, just use Bookabach'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, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in New Windsor?
A long-stay holiday home in New Windsor 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 Bookabach?
Bookabach'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 New Windsor holiday home?
Book your New Windsor 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in New Windsor?
Prices for holiday homes in New Windsor 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. Bookabach offers something for every taste and budget, from affordable homes in New Windsor to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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