Pine Island Holiday Rentals, New York: Private House Rentals

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Our top choices for Pine Island hotels

A hotel with a central entrance pavilion, a flag, and a landscaped garden.

A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.

A modern hotel lobby with a large map mural, seating areas, and a reception desk.

A boat ride with passengers holding binoculars, surrounded by water and themed structures.

1. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

Sheila

Rp2.337.140

Rp2.877.603 total

includes taxes & fees

27 Oct - 28 Oct

A hotel room with a large bed, a desk, a chair, a desk lamp, a wall-mounted TV, and a window with curtains.

A covered outdoor area with a fire pit, wooden chairs, and a view of a building with multiple windows.

A hotel entrance with stone pillars, a covered walkway, and a bench.

A modern hotel room with a flat-screen TV, a fireplace, a desk with a computer, and comfortable seating.

2. Sleep Inn & Suites Monroe - Woodbury

Monroe

John

Rp1.885.186

Rp2.132.617 total

includes taxes & fees

5 Oct - 6 Oct

A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

A two-story building with a balcony, a car parked in front, and an American flag displayed.

A pond with a gazebo, surrounded by trees and a small building in the background.

3. High Point Motel

Sussex

Dakhil

Rp1.647.076

Rp1.838.548 total

includes taxes & fees

30 Sept - 1 Oct

A room with a bed, a window with curtains, and a view of greenery outside.

A kitchen with white cabinets, a dining table with a blue chair, a window with a view of hills, and a framed picture on the wall.

A reception area with a desk, American flag, and various framed pictures on the wall.

A grassy area with a building in the background, surrounded by trees and a hill.

4. Appalachian Motel

Vernon

Naila

Rp1.007.044

Rp1.154.385 total

includes taxes & fees

30 Sept - 1 Oct

A spacious lobby with a stone fireplace, a flat-screen TV, and comfortable seating.

An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled wall.

A lobby with a stone fireplace, two armchairs, a coffee table, and a dining area with tables and chairs.

A spacious bar area with a long counter, multiple seating options, and a stone fireplace.

5. Hampton Inn Matamoras/Milford

Matamoras

brian

Rp2.069.587

Rp2.255.849 total

includes taxes & fees

6 Oct - 7 Oct

A bar area with a long counter, multiple stools, and a variety of bottles and glasses.

An indoor swimming pool with clear reflections, lounge chairs, and large windows offering views of the outdoors.

A spacious dining area with multiple tables and chairs, a high ceiling with grid patterns, and large abstract paintings on the walls.

A hallway with a wooden floor, glass doors, and a sign for Annie's Lounge.

6. Best Western Hunt's Landing Hotel Matamoras/Milford

Matamoras

Mercedes

Rp2.133.859

Rp2.325.958 total

includes taxes & fees

4 Oct - 5 Oct

A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.

A hotel room with two beds, a desk, a TV, and a chair.

A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

A gym with treadmills, a weight bench, and various exercise equipment.

7. La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

Carlos

Rp2.400.792

Rp2.835.936 total

includes taxes & fees

30 Sept - 1 Oct

A small, standalone structure with a pitched roof, possibly a gazebo or shelter, surrounded by well-maintained grass and plants. In the background, there is a sign for 'Scottish Inns' indicating the presence of a hotel nearby.

A living room with a stone fireplace, a brown leather sofa, a framed picture on the wall, and a small plant.

A row of motel-style buildings with a central statue in a landscaped area.

8. Scottish Inns Milford

Milford

Kellie

Rp1.790.300

Rp1.951.427 total

includes taxes & fees

30 Sept - 1 Oct

A room with two beds, a wooden headboard, a wall sign saying "home sweet home", and a window with a view of a car and greenery outside.

A living room with two armchairs, a coffee table, a flat-screen TV, a microwave, and a small table with a lamp.

A motel with multiple rooms, a parking lot, and a clear sky.

A bedroom with a bed, a chair, a desk with a computer, and a TV.

9. Sussex Motel

Sussex

Grace

Rp1.600.042

Rp1.786.047 total

includes taxes & fees

30 Sept - 1 Oct

A modern living room with a stone accent wall, a flat-screen TV, and a fireplace. There are multiple seating options including a sofa, chairs, and a table.

A modern restaurant with a long counter, wooden chairs, and pendant lighting.

A spacious lobby with a stone accent wall, a flat-screen TV, and a seating area with sofas and a coffee table.

An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.

10. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Aeron

Rp2.139.382

Rp2.634.137 total

includes taxes & fees

26 Oct - 27 Oct

A landscaped outdoor area with a fire feature, seating, and a pathway.

A modern hotel lobby with a fireplace, comfortable seating, and a television.

A modern bar area with a curved counter, bar stools, and a television screen.

A modern hotel lobby with a seating area, large windows, and a television screen.

11. Courtyard by Marriott Middletown Goshen

Middletown

john

Rp1.818.475

Rp2.148.072 total

includes taxes & fees

28 Oct - 29 Oct

A modern dining area with a large fish tank, sofas, and wooden tables and chairs.

An indoor swimming pool with lounge chairs and a stone wall.

A Sleep Inn & Suites hotel with a stone facade, multiple balconies, and a covered entrance.

A hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.

12. Sleep Inn & Suites Middletown - Goshen

Middletown

Rebecca

Rp1.970.762

Rp2.327.962 total

includes taxes & fees

19 Oct - 20 Oct

A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.

A conference room with multiple tables and chairs, a projector screen, and a green accent wall.

A modern restaurant with a central island, multiple tables, and chairs.

A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.

13. Home2 Suites by Hilton Middletown

Middletown

Carl

Rp2.143.347

Rp2.594.491 total

includes taxes & fees

26 Oct - 27 Oct

A hotel room with a bed, two bedside tables with lamps, a wall-mounted telephone, and a large black and white windmill painting.

A Super 8 motel sign with a parking lot and a building in the background.

A kitchenette with a microwave, toaster, and coffee maker.

A lobby with a red sofa, two lamps, a coffee table with flowers, and a wall art piece.

14. Super 8 by Wyndham Middletown

Middletown

Katelynn

Rp1.451.723

Rp1.714.848 total

includes taxes & fees

26 Oct - 27 Oct

A lobby with a fireplace, seating area, and a reception desk.

A snack and beverage display in a store with various snacks, drinks, and a 'Welcome to Harriman Woodbury' sign.

A hotel lobby with a sofa, table, chairs, and a large window offering a view of greenery.

An outdoor patio with brick flooring, round tables, and blue umbrellas.

15. Hampton Inn Harriman Woodbury

Central Valley

Oleg

Rp2.196.552

Rp2.704.503 total

includes taxes & fees

5 Oct - 6 Oct

A modern hotel room with a living area, a sofa, a coffee table, a TV, and a large window with a view.

A breakfast area with six round tables and chairs, a coffee station, and a view of greenery outside.

A multi-story building with a flat roof, multiple balconies, and a covered front porch.

16. Days Inn by Wyndham Wurtsboro

Wurtsboro

Donna

Rp1.933.524

Rp2.184.882 total

includes taxes & fees

1 Oct - 2 Oct

A brick exterior with outdoor seating, tables covered with white tablecloths, and brick walls.

A lobby with green and blue upholstered chairs, a Christmas tree, and a bar area with red bar stools.

A cozy lounge area with green and blue upholstered chairs, marble tables, and a fireplace.

A multi-story hotel with balconies, outdoor seating, and a well-lit facade.

17. The Orange Inn Boutique Hotel

Goshen

DENISE

Rp4.135.593

Rp5.091.947 total

includes taxes & fees

5 Oct - 6 Oct

A breakfast area with a counter displaying hard-boiled eggs, a bowl of green apples, and various pastries.

A modern reception area with a curved wooden counter, seating area with colorful cushions, and pendant lighting.

A modern hotel with a prominent 'tru by Hilton' sign, a covered entrance, and a well-lit facade.

An outdoor seating area with a blue sofa, round table, and chairs, under a canopy with string lights.

18. Tru by Hilton Middletown

Middletown

Steve

Rp1.754.293

Rp2.072.259 total

includes taxes & fees

26 Oct - 27 Oct

A row of white cabins with red shutters, each featuring a porch and a small front yard.

A hotel room with a double bed, a chair, a desk, a bathroom with a double sink, and a large mirror.

A counter with brochures and a vending machine.

A wooden reception desk with a sign reading "EST 1945" and various items like a framed picture, a calendar, and a display stand with cards.

19. Myer Motel

Milford

theodore

Rp1.700.785

Rp1.853.856 total

includes taxes & fees

4 Oct - 5 Oct

A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.

A modern reception area with a wooden desk, two chairs, a colorful striped artwork on the wall, and a patterned carpet.

A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.

An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.

20. Holiday Inn Express & Suites Middletown - Goshen by IHG

Middletown

Anish

Rp2.184.166

Rp2.580.046 total

includes taxes & fees

5 Oct - 6 Oct

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Stay near popular Pine Island attractions

Pine Island Town Park

Explore the great outdoors at Pine Island Town Park, a lovely green space in Pine Island. Discover the area's mountain views and seek out the ski slopes.

See properties

Scenic Farms Golf Course

Enjoy a round of golf in Pine Island at Scenic Farms Golf Course. Discover the area's mountain views and seek out the ski slopes.

See properties

Top Pine Island Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent

"Clean room and great breakfast"

Comfort Suites Central Valley - Woodbury

10/10 Excellent

"Our stay was great !"

Courtyard by Marriott Middletown Goshen

10/10 Excellent

"Excellent customer service"

Holiday Inn Express & Suites Montgomery by IHG

10/10 Excellent

"Everything was great. Next visit I will get a handicapped room. With a walk in shower."

Hampton Inn Matamoras/Milford

8/10 Good

"Staff were helpful"

More cheap stays in Pine Island

Sleep Inn & Suites Monroe - Woodbury

1 Sleep Way Monroe NY

Rp1.885.186

Rp2.132.617 total

5 Oct - 6 Oct

includes taxes & fees

Tru by Hilton Middletown

41 Dunning Road Middletown NY

Rp1.908.460

Rp2.254.368 total

5 Oct - 6 Oct

includes taxes & fees

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

Rp1.970.762

Rp2.327.962 total

19 Oct - 20 Oct

includes taxes & fees

8.8/10 Excellent! (1,201 reviews)

Comfort Suites Central Valley - Woodbury

100 Estrada Road Central Valley NY

Rp2.120.325

Rp2.610.650 total

5 Oct - 6 Oct

includes taxes & fees

8.4/10 Very good! (172 reviews)

Hampton Inn Harriman Woodbury

60 Centre Dr Central Valley NY

Rp2.196.552

Rp2.704.503 total

5 Oct - 6 Oct

includes taxes & fees

Holiday Inn Express Hotel & Suites Chester by IHG

2 Bryle Place Chester NY

Rp2.337.140

Rp2.877.603 total

27 Oct - 28 Oct

includes taxes & fees

Frequently asked questions

What's the best place to stay in Pine Island?

Sleep Inn & Suites Middletown - Goshen, located 8.6 mi (13.8 km) from the heart of Pine Island, is a top choice for your stay, based on our traveller data. Other good options for your stay in the area are La Quinta Inn & Suites by Wyndham Middletown-Goshen and Holiday Inn Express Hotel & Suites Chester by IHG. See all available top hotels, or vacation rentals in Pine Island.

If I need to cancel my hotel reservation in Pine Island, will I receive a refund?

Yes! You'll find that most hotel room reservations are fully refundable as long as you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Pine Island.

What is staying in Pine Island like?

Visitors can enjoy all that Pine Island has to offer, including the golf courses, mountain views and riverfront. This city also attracts tourists with its welcoming locals. There are 679 hotels and other accommodation options in the surrounding area. Find out more about Pine Island.

What should I do while I'm visiting Pine Island?

A couple of favourite places to visit are Pine Island Town Park and Scenic Farms Golf Course. You'll also find Warwick Valley Winery and Distillery and Applewood Winery in the area. Take a look at what more there is to see and do in Expedia's Pine Island guide.

What's the seasonal weather like in Pine Island?

The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Pine Island are February, January, November and March, with each month seeing an average of 18 cm of snowfall.

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Book Hotels in Pine Island on Expedia.com

Find hotels in Pine Island, NY from Rp1.154.385

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Pine Island

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Pine Island hotels

1. Holiday Inn Express Hotel & Suites Chester by IHG

2. Sleep Inn & Suites Monroe - Woodbury

3. High Point Motel

4. Appalachian Motel

5. Hampton Inn Matamoras/Milford

6. Best Western Hunt's Landing Hotel Matamoras/Milford

7. La Quinta Inn & Suites by Wyndham Middletown-Goshen

8. Scottish Inns Milford

9. Sussex Motel

10. Fairfield Inn & Suites by Marriott Goshen Middletown

11. Courtyard by Marriott Middletown Goshen

12. Sleep Inn & Suites Middletown - Goshen

13. Home2 Suites by Hilton Middletown

14. Super 8 by Wyndham Middletown

15. Hampton Inn Harriman Woodbury

16. Days Inn by Wyndham Wurtsboro

17. The Orange Inn Boutique Hotel

18. Tru by Hilton Middletown

19. Myer Motel

20. Holiday Inn Express & Suites Middletown - Goshen by IHG

Stay near popular Pine Island attractions

Pine Island Town Park

Scenic Farms Golf Course

Top Pine Island Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Comfort Suites Central Valley - Woodbury

Courtyard by Marriott Middletown Goshen

Holiday Inn Express & Suites Montgomery by IHG

Hampton Inn Matamoras/Milford

More cheap stays in Pine Island

Sleep Inn & Suites Monroe - Woodbury

Tru by Hilton Middletown

Sleep Inn & Suites Middletown - Goshen

Comfort Suites Central Valley - Woodbury

Hampton Inn Harriman Woodbury

Holiday Inn Express Hotel & Suites Chester by IHG

Frequently asked questions

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