Pine Island Holiday Rentals

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Holiday Rentals in Pine Island

Mid-Hudson Estate on 11 acres with pool

10.0 out of 10, Exceptional, (6)
"We were pleased with every aspect of our stay. The property fully fulfilled all our needs. Highly recommended!"
The price is NZ$11,029
includes taxes & fees
5 July - 6 July
Mid-Hudson Estate on 11 acres with pool

5BR Home with Sauna & Pool Hot tub Fire pit

The price is NZ$2,347
includes taxes & fees
2 July - 3 July
5BR Home with Sauna & Pool Hot tub Fire pit

The Perfect Essential Getaway!

9.6 out of 10, Exceptional, (5)
"Owner was very responsive and accommodating on the app when I had questions. Place was great."
The price is NZ$2,110
includes taxes & fees
30 June - 1 July
The Perfect Essential Getaway!

Amazing Home Near West Point, Shopping, Skiing and Legoland

10.0 out of 10, Exceptional, (12)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
The price is NZ$961
includes taxes & fees
29 June - 30 June
Amazing Home Near West Point, Shopping, Skiing and Legoland

Waterfront Modern Home with Fast Wifi & Hot Tub

9.8 out of 10, Exceptional, (16)
"The house was very clean and beautiful inside. Beds were incredibly comfortable, short distance to town and skiing at Mt Peter which was the reason for our visit. Spa was clean although we didn’t use it because there was a snow storm. Overall great visit!"
The price is NZ$1,139
includes taxes & fees
14 July - 15 July
Waterfront Modern Home with Fast Wifi & Hot Tub

Charming 3-BR house: Lake Views, Firepit, Ping Pong, & Kayaks in Greenwood Lake

10.0 out of 10, Exceptional, (1)
"The location was fantastic and the place was amazing. Our family enjoyed the great views and the house had all the amenities to spend a relaxing vacation. "
The price is NZ$1,259
includes taxes & fees
6 July - 7 July
Charming 3-BR house: Lake Views, Firepit, Ping Pong, & Kayaks in Greenwood Lake

Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck ~ Living Room

10.0 out of 10, Exceptional, (1)
"We had an amazing stay at this beautiful home! The views overlooking the lake and mountains are absolutely breathtaking—better than I could have imagined. The house itself is gorgeous, well-maintained, and equipped with everything needed for a comfortable stay. On top of that, the host was incredibly responsive and made sure everything was perfect. If you’re looking for a peaceful retreat with unbeatable scenery and top-notch hospitality, this is the place to be. I can't wait to return!"
The price is NZ$1,738
includes taxes & fees
30 June - 1 July
Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck ~ Living Room

Secluded Stunning Lake View Villa w Heated Pool, Fenced Yard & Hot Tub

9.8 out of 10, Exceptional, (8)
"Incredible place, scenic views, newly renovated house me and my family enjoyed it all! Besides that the host was very responsive and friendly."
The price is NZ$2,899
includes taxes & fees
29 June - 30 June
Secluded Stunning Lake View Villa w Heated Pool, Fenced Yard & Hot Tub

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

2.0 star property
The price is NZ$875
includes taxes & fees
8 July - 9 July
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

10.0 out of 10, Exceptional, (24)
"A beautiful and bright cottage in a serene but convenient location. It was thoughtfully set up for a family getaway and was exceptionally clean. My entire family enjoyed the stay!"
The price is NZ$1,577
includes taxes & fees
30 June - 1 July
New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Spectacular Mansion w/Pool&Tennis

10.0 out of 10, Exceptional, (9)
"We had a great time with our extended family at this beautiful house. The tennis court and swimming pool were great additions to our stay and vacation. Some minor issues arose, but the owner was incredibly responsive and moved to fix any issues quickly and successfully. Would stay again!"
The price is NZ$5,663
includes taxes & fees
10 July - 11 July
Spectacular Mansion w/Pool&Tennis

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

9.8 out of 10, Exceptional, (53)
"We had a wonderful stay! The house is in a beautiful location, everything was well appointed, instructions were easy to follow and the house itself was perfect. "
The price is NZ$927
includes taxes & fees
27 July - 28 July
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Dream escape, new modern farmhouse, stunning views, game room & hot tub for 17+!

10.0 out of 10, Exceptional, (12)
"We loved our stay here! The property is gorgeous and the hosts were helpful and communicative. The house was clean and had everything we needed."
The price is NZ$1,885
includes taxes & fees
9 July - 10 July
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 17+!

Serene and modern Woodland Retreat, Hudson Valley & Catskills

The price is NZ$844
includes taxes & fees
1 July - 2 July
Serene and modern Woodland Retreat, Hudson Valley & Catskills

3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

The price is NZ$683
includes taxes & fees
7 July - 8 July
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

Large Family House On The Lake

9.6 out of 10, Exceptional, (58)
"It was perfect for us. We have stayed 7 guys and had a lot of fun. "
The price is NZ$1,361
includes taxes & fees
16 July - 17 July
Large Family House On The Lake

Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

8.0 out of 10, Very good, (2)
"I stayed here for the weekend to hike a small section of the AT. It was perfect for my trip. "
The price is NZ$262
includes taxes & fees
30 June - 1 July
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

The Warwick Inn Boutique Amity Room 3 an Hour from NYC

8.6 out of 10, Excellent, (4)
"Was happy with the room, nice property easy to walk to main street. Would stay there again."
The price is NZ$313
includes taxes & fees
6 July - 7 July
The Warwick Inn Boutique Amity Room 3 an Hour from NYC

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

The price is NZ$277
includes taxes & fees
29 June - 30 June
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

The price is NZ$305
includes taxes & fees
30 June - 1 July
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Can I find a holiday rental in Pine Island?

Yes, we have holiday rentals where you'll be just 9.3 mi (15 km) from LEGOLAND® New York, offering you a more secluded option if you want a quiet place to stay. Pine Island is known for its golf courses and mountain views. Make sure you have time to check out the riverfront while you're in the area.

What are some of the best holiday rentals that Pine Island has to offer?

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out: This holiday home rental outside of Pine Island is located in the mountains, and has an outdoor pool, a fireplace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Pine Island?

While exploring the area, visit family-friendly sights like LEGOLAND® New York, or get outside and enjoy nature at Pine Island Town Park. Scenic Farms Golf Course and Warwick Valley Winery and Distillery are a couple of places you'll find in the wider area.

What are holiday rentals like in Pine Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pine Island. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip.