Find hotels in Pine Island, NY from ฿2,246

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Our top choices for Pine Island hotels

Exterior
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1000)
Experience peaceful accommodation just 10 minutes from LEGOLAND® New York. This Middletown hotel offers a seasonal outdoor pool, fitness centre, free breakfast, and parking. Guests praise the helpful staff, clean rooms, and convenient access to Galleria at Crystal Run.
"Room was clean and staff was great!"
United States
Annemarie
The price is ฿2,485
฿2,936 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hampton Inn by Hilton Middletown
Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1004)
Experience effortless shopping trips with a stay just 10 minutes from Woodbury Common Premium Outlets and LEGOLAND. This hotel offers a fitness centre, daily complimentary breakfast, and thoughtful in-room amenities like refrigerators and microwaves.
"The room was very clean, comfortable bed, good service and at a reasonable price."
Canada
DIMITRIOS
The price is ฿2,679
฿3,030 total
includes taxes & fees
20 Jan - 21 Jan 2026
Sleep Inn & Suites Monroe - Woodbury
Lobby
Quality Inn near Mountain Creek

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (977)
This quiet hotel offers easy access to Mountain Creek Ski Resort and Crystal Springs Golf Resort. Enjoy free breakfast, WiFi, and parking after a day of skiing. The fitness centre keeps your routine intact while helpful staff ensures a comfortable mountain getaway.
"Nice hotel. Close to golf,"
United States
Joseph
The price is ฿2,692
฿3,086 total
includes taxes & fees
12 Jan - 13 Jan 2026
Quality Inn near Mountain Creek
Exterior
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.4 out of 10, Very good, (1001)
Perfectly positioned for family adventures, this Chester hotel offers free breakfast, WiFi and parking. Take a refreshing swim in the indoor pool after exploring nearby LEGOLAND® or shopping at Woodbury Common Premium Outlets. Clean rooms and attentive staff ensure a comfortable stay.
"The breakfast was a hit, the place is clean and I would stay here again."
United States
elizabeth
The price is ฿2,955
฿3,491 total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Reception
Tru by Hilton Middletown

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (959)
Experience comfort at this Middletown hotel with complimentary English breakfast and WiFi. Just a short drive from LEGOLAND® New York and Orange County Fairgrounds, guests can enjoy the 24-hour fitness centre and outdoor terrace after a day of adventures.
"Staff both during check in and out were great . Great stay ."
United States
david
The price is ฿2,780
฿3,284 total
includes taxes & fees
1 Jan - 2 Jan 2026
Tru by Hilton Middletown
Seasonal outdoor pool, pool umbrellas, pool loungers
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
Immerse in family fun at this colourful hotel featuring an outdoor pool and restaurant near LEGOLAND® New York. Free breakfast energises morning adventures, while themed rooms create magical memories. Charles J. Everett Memorial attraction is located nearby.
"We are having a great time at the hotel!!!"
United States
Ziwei
The price is ฿5,924
฿10,780 total
includes taxes & fees
2 Jan - 3 Jan 2026
LEGOLAND Hotel NEW York
Indoor pool, pool loungers
Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford
3.0 star property
Matamoras
8.4 out of 10, Very good, (1000)
Discover tranquil accommodation at this Matamoras hotel featuring an indoor pool and fitness centre. Enjoy complimentary breakfast, WiFi, and parking while exploring nearby Westfall Town Centre and Marie's Flea Market. Guests consistently praise the peaceful atmosphere and helpful staff.
"breakfast was excellent, good variety, hot, very clean - great staff member she deserves a kudo!"
United States
Clark
The price is ฿2,829
฿3,084 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Hunt's Landing Hotel Matamoras/Milford
View from property
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
2.5 star property
Goshen
8.8 out of 10, Excellent, (1001)
Located just 5 minutes from LEGOLAND® New York, this hotel offers a seasonal outdoor pool and 24-hour fitness centre. Guests love the free hot breakfast, convenient parking, and helpful staff. Charles J. Everett Memorial and Stewart Airport are nearby for added exploration options.
"Rooms were clean and as expected. Bed was a bit soft for our taste, but acceptable. Breakfast options were routine, scrambled eggs, bacon or sausage on alternating days, oatmeal, waffles, bagel, toast, English muffins... Pleasant and helpful staff, smooth check-in and check-out. Overall a pleasant place."
United States
Joon
The price is ฿3,142
฿3,868 total
includes taxes & fees
1 Jan - 2 Jan 2026
Fairfield Inn & Suites by Marriott Goshen Middletown
Fireplace
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1004)
Located 10 minutes from LEGOLAND® New York, this hotel offers American cuisine at The Bistro restaurant and bar. Enjoy the indoor pool, 24-hour fitness centre, free WiFi, and parking while staying near Galleria at Crystal Run.
"The hotel was very clean, enjoyed my stay would recommend "
United States
Jessica
The price is ฿2,882
฿3,404 total
includes taxes & fees
28 Dec - 29 Dec
Courtyard by Marriott Middletown Goshen
King Suite | Living area | 40-inch Smart TV with cable channels, TV, Netflix
Tom Quick Inn

Tom Quick Inn

Tom Quick Inn
3.5 star property
Milford
9.0 out of 10, Wonderful, (153)
Savour free breakfast at Tom Quick Inn Restaurant before exploring The Columns Museum nearby. This inn offers a welcoming bar, peaceful terrace, and attentive staff to enhance your stay, plus convenient free WiFi and parking.
"The room was comfy and the staff was very welcoming."
United States
Mary
Tom Quick Inn
Lobby
Hampton Inn Matamoras/Milford

Hampton Inn Matamoras/Milford

Hampton Inn Matamoras/Milford
2.5 star property
Matamoras
8.8 out of 10, Excellent, (1001)
Discover comfort at this Matamoras hotel featuring an indoor pool for refreshing swims year-round. Located near Marie's Flea Market, guests enjoy free breakfast, WiFi, and parking. The helpful staff and 24-hour fitness centre ensure a pleasant stay.
"Clean room, decent breakfast, courteous staff. "
United States
Christopher E
The price is ฿3,035
฿3,309 total
includes taxes & fees
16 Jan - 17 Jan 2026
Hampton Inn Matamoras/Milford
Room, 2 Queen Beds, Non Smoking | In-room safe, desk, iron/ironing board, free cots/infant beds
Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (596)
"Very clean and quiet "
United States
Jeanette
The price is ฿2,955
฿3,339 total
includes taxes & fees
28 Dec - 29 Dec
Days Inn by Wyndham Wurtsboro
Exterior detail
Borland House Inn

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (144)
This Montgomery Victorian B&B offers a tranquil garden and terrace, with luxury facial treatments available. Located near City Winery Hudson Valley, the inn provides free breakfast, WiFi, and parking for a comfortable getaway.
"Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast"
United States
Deborah
Borland House Inn
Exterior
Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
2.5 star property
Montgomery
8.8 out of 10, Excellent, (801)
Located near the train station, this welcoming hotel offers a 24-hour health club and coffee shop. Just minutes from City Winery Hudson Valley and Orange County Farmers Museum, guests appreciate the helpful staff, clean rooms, and free parking.
"Clean quiet and nice reception "
United States
Nick
The price is ฿2,800
฿3,167 total
includes taxes & fees
7 Jan - 8 Jan 2026
Holiday Inn Express & Suites Montgomery by IHG
BBQ/picnic Area
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.6 out of 10, Excellent, (1000)
Enjoy easy access to LEGOLAND® New York from this welcoming Middletown hotel. Start your day with free breakfast before swimming in the indoor pool. After exploring nearby Paramount Theatre, return to comfortable rooms with complimentary WiFi and parking.
"Love this hotel "
United States
Jennifer
The price is ฿3,200
฿3,781 total
includes taxes & fees
11 Jan - 12 Jan 2026
Sleep Inn & Suites Middletown - Goshen
Comfort Room, 2 Double Beds, Non Smoking, Refrigerator & Microwave | Free WiFi, bed sheets
Sussex Motel

Sussex Motel

Sussex Motel
2.5 star property
Sussex
8.8 out of 10, Excellent, (370)
Just 15 minutes from Crystal Springs Golf Resort and Mountain Creek Waterpark, this welcoming motel provides free WiFi and parking. Explore local hiking trails before returning to your comfortable, clean room with daily housekeeping service.
"Kind lady. Warm room. Can’t complain"
United States
Taewoung
The price is ฿2,426
฿2,708 total
includes taxes & fees
25 Dec - 26 Dec
Sussex Motel
Free self-parking
Appalachian Motel

Appalachian Motel

Appalachian Motel
2.0 star property
Vernon
7.6 out of 10, Good, (515)
Set in Vernon, this inviting motel provides easy access to Mountain Creek Waterpark and Ski Resort. Enjoy hiking trails and snowboarding nearby, plus convenient amenities like room service, making it perfect for adventure seekers.
"I would stay here again"
United States
Lyanlex
The price is ฿1,960
฿2,246 total
includes taxes & fees
1 Jan - 2 Jan 2026
Appalachian Motel
Terrace/patio
High Point Motel

High Point Motel

High Point Motel
2.0 star property
Sussex
9.0 out of 10, Wonderful, (105)
Escape to Sussex at this cosy motel offering complimentary amenities and a relaxing garden. Located near High Point State Park and Dryden Kuser Natural Area, it's an ideal base for outdoor adventures.
"Great place to stay"
United States
Bob
The price is ฿2,737
฿3,056 total
includes taxes & fees
28 Dec - 29 Dec
High Point Motel
Exterior
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (941)
The indoor pool and free breakfast enhance this quiet retreat near restaurants and highways. Just 15 minutes from LEGOLAND® New York, guests appreciate the helpful staff, clean rooms, fitness centre, and free WiFi and parking.
"Room was large and spacious ~ perfect for all the luggage we brought"
United States
Cynthia
The price is ฿3,675
฿4,341 total
includes taxes & fees
28 Dec - 29 Dec
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Room, 2 Double Beds, Non Smoking | Desk, blackout curtains, iron/ironing board, free WiFi
Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
2.0 star property
Central Valley
7.2 out of 10, Good, (1001)
Steps from LEGOLAND® New York, this value-friendly motel offers complimentary WiFi and parking. Clean rooms provide a comfortable base for shopping excursions to nearby Woodbury Common Premium Outlets, while the attentive staff ensures a pleasant stay.
"Room was perfect, motel in good location, excellent value"
United States
Paul
The price is ฿2,537
฿3,124 total
includes taxes & fees
31 Dec - 1 Jan 2026
Americas Best Value Inn at Central Valley-Woodbury
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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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

Hampton Inn Matamoras/Milford

Hampton Inn Matamoras/Milford

10/10 Excellent
"Clean ,well maintained and great breakfast."
george 1-night trip
Posted 6 days ago
Hampton Inn Matamoras/Milford

More cheap stays in Pine Island

Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

563 Route 211 E Middletown NY
The price is ฿2,353 per night from 28 Dec to 29 Dec
฿2,353
฿2,780 total
28 Dec - 29 Dec
includes taxes & fees
6/10 (1,000 reviews)

Frequently asked questions

What's the best place to stay in Pine Island?
Hampton Inn Harriman Woodbury, located 17.2 mi (27.7 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 Best Western Hunt's Landing Hotel Matamoras/Milford and Sleep Inn & Suites Monroe - Woodbury. 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 636 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 Warwick Village Hall 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.