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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Pine Island holiday rentals

A modern kitchen with dark cabinets, a stainless steel stove, and a wooden countertop.

1. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
10.0 out of 10, Exceptional, (2 reviews)
"Great for a group"
United States
Audra
Carriage House Apartment Goshen NY
A spacious loft with a high ceiling, exposed beams, a kitchen with modern appliances, a dining area, and a living room with a large sofa.

2. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
10.0 out of 10, Exceptional, (4 reviews)
"The apartment was very clean and well decorated. Our host Emily was very lovely and responsive whenever we needed help. The breakfast provided at the Inn was delicious as well. Would definitely recommend this stay!"
United States
Natasha
Hay Loft Apartment in Barn - Goshen
A two-story house with a porch, a table, and chairs outside.

3. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
3.5 star property
Goshen
Historic Horse Barn Apartment in Goshen
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

4. Columbus Suites

Columbus Suites
3.0 star property
Middletown
6.4 out of 10, (21 reviews)
"My worst experience ever staying at the hotel no communication locked out at the sleep in my car. I would never recommend anybody to stay there. The bed is horrible no curtains window basically nothing nice to say about that property. Sorry."
United States
Edwin
The price is ฿2,100
฿4,867 total
includes taxes & fees
16 Nov - 17 Nov
Columbus Suites
A spacious living room with a fireplace, a ceiling fan, and a large window.

5. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
The price is ฿7,181
฿18,272 total
includes taxes & fees
30 Nov - 1 Dec
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

6. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is ฿7,181
฿11,639 total
includes taxes & fees
15 Nov - 16 Nov
Hike & Fish: Outdoor Retreat Near Trails
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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Top Pine Island Hotel Reviews

A modern dining area with a large fish tank, sofas, and wooden tables and chairs.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown

10/10 Excellent

Excellent
United Kingdom
Rosemarie
Reviewed January 17, 2026
Sleep Inn & Suites Middletown - Goshen

Find out more about Pine Island

Search for holiday rentals in Pine Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Pine Island using one of the methods below:

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Look no further and take a look at our great range of rental properties in Pine Island!

Frequently Asked Questions

Can I find a holiday rental in Pine Island?

Yes, there are holiday rentals close to the most popular sights in Pine Island, or you can select a more secluded option if you're looking for a relaxing 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 can I see and do in Pine Island?

While exploring the area, visit family-friendly sights like Mountain Creek Waterpark, 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.