Pine Island holiday rentals

We found 315 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Pine Island that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a hot tub. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Pine Island

Showing deals for:15 Jan - 22 Jan

Outdoor dining
Private kitchen
Interior
Exterior
Exceptional
(13 reviews)

Spacious Westtown Home, Firepit, Up to 10 Guest

Westtown

8% off
AU$3,554
for 7 nights, 1 home
AU$508 per night
includes taxes & fees
Spacious Westtown Home, Firepit, Up to 10 Guest
Living area
Private kitchen
Exterior
Pool
Exceptional
(5 reviews)

Saltwater Heated Pool • Perfect Escape in Warwick

Warwick

8% off
AU$4,251
for 7 nights, 1 home
AU$607 per night
includes taxes & fees
Saltwater Heated Pool • Perfect Escape in Warwick
Lobby
Pool
Interior
Living area
Exceptional
(12 reviews)

Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

Vernon

8% off
AU$3,414
for 7 nights, 1 apartment
AU$488 per night
includes taxes & fees
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Interior
Pool
Living area
Property grounds
Wonderful
(15 reviews)

New condo:Mineral Spa Mt Creek

Vernon

7% off
AU$2,073
for 7 nights, 1 apartment
AU$296 per night
includes taxes & fees
New condo:Mineral Spa Mt Creek
Deck
Kitchen Island
Living Room with sofa bed
2nd Floor Apt with Private Entrances, front and back.
Exceptional
(67 reviews)

Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries

Chester

7% off
AU$2,188
for 7 nights, 1 apartment
AU$313 per night
includes taxes & fees
Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
Dining
Large contemporary addition opening up on big deck with steps down to the yard!
10' table with amazing views to backyard and out onto the deck
Imagine walking into this!
Wonderful
(32 reviews)

Contemporary Cottage less than an hour from NYC!

Highland Lakes

8% off
AU$3,321
for 7 nights, 1 home
AU$474 per night
includes taxes & fees
Contemporary Cottage less than an hour from NYC!

  • 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 friendly area of Pine Island awaits your stay

The mountains, parks and riverfront are the perfect backdrop to your holiday home in Pine Island. Travellers appreciate the golfing in this welcoming city. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Pine Island

Are you looking for attractions to visit in the city? Venture out of your holiday home and experience everything that makes Pine Island a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Warwick Valley Winery and Distillery (1.1 mi / 1.7 km)
  • Applewood Winery (7.8 mi / 12.5 km)
  • Mountain Creek Waterpark (7.9 mi / 12.8 km)
  • Mountain Creek Ski Resort (8.8 mi / 14.1 km)
  • Mount Peter Ski Area (9.3 mi / 15 km)
  • LEGOLAND® New York (9.3 mi / 15 km)

Exploring the natural landscape of Pine Island

Whether you're an active traveller or just want to take in the scenery, Pine Island is a great place to spend some time outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Upper Greenwood Lake (9.5 mi / 15.2 km)
  • The Rock Sports Complex (10 mi / 16.1 km)
  • Greenwood Lake (10.5 mi / 17 km)
  • Sterling Lake (12.1 mi / 19.5 km)
  • Sterling Forest State Park (12.6 mi / 20.3 km)
  • Arrow Park Lake and Lodge (14.7 mi / 23.6 km)

Transport to and around Pine Island

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 23.8 mi (38.4 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Caldwell, NJ (CDW-Essex County), which is 30.7 mi (49.3 km) away.

Frequently asked questions

What is the best area to stay in Pine Island when booking a holiday rental?
When considering a holiday rental in Pine Island, New York, the area around the Pine Island area itself is particularly appealing. This charming spot is renowned for its beautiful rural landscape and outdoor activities. A popular attraction nearby is the scenic Black Dirt Region, which is famous for its fertile soil and stunning views, making it superb for leisurely drives or hikes.In addition to its natural beauty, Pine Island is home to local farms and markets, offering fresh produce and artisanal products that visitors can enjoy. The area has a selection of properties available, suiting various preferences and budgets, from quaint cottages to larger family homes. Staying here provides a peaceful retreat while remaining conveniently close to the vibrant communities of Warwick and Goshen, where you can explore more shops, restaurants, and cultural sites.
When is the best time to visit Pine Island for a holiday rental?
April is widely regarded as the best time to visit Pine Island, as it falls within the peak season from February to April. During this period, visitors can engage in the beauty of the region as spring begins to unfold. With warmer temperatures ranging from about 5 to 15 degrees Celsius, it's an ideal time for outdoor activities such as hiking, cycling, and exploring the picturesque landscapes.As the weather becomes increasingly pleasant, tourists flock to the area to enjoy the vibrant local flora and fauna. The peak season not only offers an array of outdoor adventures but also the chance to connect with fellow travellers who share a passion for nature and exploration.For those looking for more budget-friendly options, consider visiting in December. During this time, this month provides a unique opportunity to experience the tranquility of Pine Island during the winter months, allowing for peaceful walks and a chance to enjoy the local holiday spirit.
What are the top attractions in Pine Island?
Pine Island is known for its rural charm and beautiful landscapes, making it an ideal destination for those seeking a peaceful retreat. One of the main attractions is the scenic Pine Island Park, which offers walking trails, picnic areas, and lovely views of the surrounding countryside, superb for a day out in nature.The area is also renowned for its agricultural heritage, with several local farms and orchards that often welcome visitors for fruit-picking seasons, particularly apples and pumpkins. Additionally, the Pine Island Farmers Market, held regularly, showcases local produce and artisanal goods, providing a taste of the community spirit.For a bit of history, visitors can explore the nearby historic sites, including the remnants of the old Pine Island Schoolhouse, which reflects the area's past. Nature enthusiasts will appreciate the proximity to the Wallkill River, where activities such as fishing and kayaking can be enjoyed.
Are all fees included in the Pine Island 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 Pine Island holiday homes with parking?
Stayz offers a wide selection of holiday homes in Pine Island 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 Pine Island holiday homes?
You can find great discounts on holiday homes in Pine Island 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 Pine Island holiday home booking on Stayz?
To find Pine Island 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 Pine Island?
A long-stay holiday home in Pine Island 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 Pine Island holiday home?
Book your Pine Island 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 Pine Island?
Prices for holiday homes in Pine Island 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 Pine Island 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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