Find hotels in Highland Mills, NY from ₩125,613

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Our top choices for Highland Mills hotels

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
8.6 out of 10, Excellent, (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 ₩121,102
₩143,051 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Hotel & Suites Chester by IHG
Free daily buffet breakfast
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie
2.5 star property
Crown Heights
8.8 out of 10, Excellent, (1001)
Enjoy free breakfast, WiFi, and parking at this hotel with a fitness center and terrace. Hike nearby trails or explore Casperkill Golf Club. Each room includes refrigerators and microwaves, all just 10 minutes from Vassar College and 13 minutes from the station.
"Great stay with many breakfast options! "
United States
Sara
The price is ₩138,056
₩160,317 total
includes taxes & fees
Dec 27 - Dec 28
Hampton Inn & Suites Poughkeepsie
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1001)
Historic lodge near Bear Mountain State Park offers deep-tissue massages and body wraps at the onsite spa. Enjoy drinks at the bar, meals at the café, and rooms with refrigerators and microwaves. Free WiFi and parking add convenience for exploring nearby attractions.
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is ₩175,677
₩198,736 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Overlook Lodge at Bear Mountain
Reception
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1007)
Dive into this hotel's indoor pool after exploring nearby Van Wyck Homestead Museum. Enjoy a meal at Great American Grille before retreating to rooms with refrigerators and microwaves. The 24-hour fitness center and helpful staff enhance your stay.
"Brayden was great"
United States
Will
The price is ₩135,272
₩153,026 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hilton Garden Inn Fishkill
Indoor pool, open 8:30 AM to 9:30 PM, sun loungers
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
8.8 out of 10, Excellent, (1008)
Adjacent to a golf course, this serene Nanuet hotel boasts an indoor pool and Windsor Grille for evening dining. The peaceful atmosphere, 24-hour fitness center, and bar create the perfect setting for unwinding near Rockland Bakery and The Shops at Nanuet.
"Great staff, clean and the pool was awesome! "
Canada
Aleah
The price is ₩144,055
₩167,645 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Hotel Nanuet
Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, 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, (1001)
Experience effortless shopping trips with a stay just 10 minutes from Woodbury Common Premium Outlets and LEGOLAND. This hotel offers a fitness center, daily complimentary breakfast, and thoughtful in-room amenities like refrigerators and microwaves.
"Clean. Easy exit off highway. Great hotel for the price just needed a safe clean overnight bed."
Canada
Mary
The price is ₩129,056
₩145,995 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Sleep Inn & Suites Monroe - Woodbury
Seasonal outdoor pool, pool umbrellas, sun 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 colorful hotel featuring an outdoor pool and restaurant near LEGOLAND® New York. Free breakfast energizes 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 ₩281,104
₩511,512 total
includes taxes & fees
Dec 22 - Dec 23
LEGOLAND Hotel NEW York
Free daily English breakfast
Tru by Hilton Middletown

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (958)
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 center 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 ₩144,111
₩170,232 total
includes taxes & fees
Dec 25 - Dec 26
Tru by Hilton Middletown
Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84
2.5 star property
Fishkill
8.8 out of 10, Excellent, (1002)
Conveniently located near a train station, this Fishkill hotel offers complimentary continental breakfast, WiFi, and parking. Work out in the fitness center before exploring nearby Fishkill Golf Course and Fishkill Ridge. Guests praise the clean rooms and helpful staff.
"Always stay here on my way through NY."
United States
Kathleen
The price is ₩131,758
₩149,051 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Quality Inn & Suites Fishkill South near I-84
Lobby
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (999)
Situated conveniently near a train station in Fishkill, this hotel features free WiFi and parking. Guests love the comfortable beds and helpful staff. After working out in the fitness center, enjoy a refreshing swim in the indoor pool year-round.
"Yes stay was pleasant "
United States
henry
The price is ₩138,032
₩156,151 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Comfort Suites Fishkill near Interstate 84
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, (796)
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.
"Good stay"
United States
Fatima
The price is ₩132,865
₩150,303 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express & Suites Montgomery by IHG
Lobby
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 accommodations just 10 minutes from LEGOLAND® New York. This Middletown hotel offers a seasonal outdoor pool, fitness center, 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 ₩122,826
₩145,089 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hampton Inn by Hilton Middletown
Indoor pool
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very Good, (1010)
Located just minutes from Stewart Airport, this welcoming hotel offers a refreshing indoor pool and convenient fitness center. Enjoy free WiFi and parking while exploring nearby Resorts World Hudson Valley and Hamilton Fish Bridge.
"Love it, everytime we come this is the place to stay"
United States
William
The price is ₩149,147
₩168,722 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
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, (939)
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 center, and free WiFi and parking.
"great staff, clean rooms, nice breakfast .. overall a pleasant & safe atmosphere !"
United States
Emerson
The price is ₩155,660
₩183,873 total
includes taxes & fees
Dec 23 - Dec 24
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Exterior
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley
3.0 star property
Crown Heights
9.0 out of 10, Wonderful, (1010)
"very clean and would stay again "
United States
Alvin
The price is ₩149,162
₩173,214 total
includes taxes & fees
Dec 28 - Dec 29
Hyatt Place Poughkeepsie / Hudson Valley
Reception
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 center. 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 ₩149,162
₩183,654 total
includes taxes & fees
Dec 28 - Dec 29
Fairfield Inn & Suites by Marriott Goshen Middletown
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
Free continental breakfast on weekdays
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 ₩143,550
₩169,569 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Sleep Inn & Suites Middletown - Goshen
Exterior
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG
3.5 star property
Suffern
8.8 out of 10, Excellent, (1002)
Surrounded by tranquility in Suffern, this hotel offers spacious rooms with comfortable beds and American cuisine at Flagstone Restaurant. The 24-hour fitness center, garden, and helpful staff create a relaxing retreat near local museums with free WiFi and parking.
"Good location"
United States
Glenn
The price is ₩168,296
₩195,856 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Crowne Plaza Suffern - Mahwah by IHG
View from property
Courtyard by Marriott Fishkill

Courtyard by Marriott Fishkill

Courtyard by Marriott Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (733)
Escape to a tranquil hotel with an indoor pool and fitness center, just minutes from Van Wyck Homestead Museum. The Bistro serves tasty meals while helpful staff ensure a comfortable stay near Fishkill Golf Course.
"Great Stay!"
United States
Les
The price is ₩161,874
₩183,120 total
includes taxes & fees
Dec 21 - Dec 22
Courtyard by Marriott Fishkill
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 Highland Mills attractions

Palaia Vineyards Winery

This hippie-inspired winery in a 200-year-old barn pairs distinctive wines and meads with weekend live music. Enjoy vineyard views from the outdoor stage or relax in the rustic tasting room with artisanal pizzas.
See properties

Top Highland Mills Hotel Reviews

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"Great staff, comfy room "
Andrew 1-night trip
Posted 3 days ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

More cheap stays in Highland Mills

Hotel Mint JFK Airport

Hotel Mint JFK Airport

10-74 Beach 22nd St Far Rockaway NY
The price is ₩104,963 per night from Dec 22 to Dec 23
₩104,963
₩125,613 total
Dec 22 - Dec 23
includes taxes & fees
5.4/10 (1,653 reviews)

Frequently asked questions

What's the best place for a stay in Highland Mills?
Located 19 mi (30.5 km) from the heart of Highland Mills, DoubleTree by Hilton Hotel Nanuet is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are Sonesta Simply Suites Nanuet and Crowne Plaza Suffern - Mahwah by IHG. See all available top hotels, or vacation rentals in Highland Mills.
If I need to cancel my hotel reservation in Highland Mills, will I receive a refund?
Yes! Most hotel room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Highland Mills.
Where can I learn more about changing or cancelling my trip to Highland Mills?
For more information about rescheduling or cancelling your trip to Highland Mills, click here.
What's the best hotel to stay close to Palaia Vineyards Winery?
Hampton Inn Harriman Woodbury is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and an indoor pool. It's located 4.7 mi (7.5 km) from Palaia Vineyards Winery. Other good choices within a few miles include Americas Best Value Inn Central Valley and Caldwell House Bed & Breakfast.
What are some accommodations with pools in Highland Mills?
DoubleTree by Hilton Hotel Nanuet: Features a snack bar/deli, a pool, and free self parking. Hampton Inn Harriman Woodbury and Overlook Lodge at Bear Mountain are a couple of other choices that offer an onsite pool. View all hotels with pools in Highland Mills.
What's the best accommodation near Stewart International Airport (SWF)?
Howard Johnson by Wyndham Newburgh is a popular hotel, featuring free breakfast and free WiFi. It's located a short 0.8 mi (1.2 km) from Stewart Intl. Airport. Other options within close proximity to the airport include Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport and Super 8 by Wyndham Newburgh/West Point Near Stewart Airport.
How is it to stay in Highland Mills?
Visitors can enjoy all that Highland Mills has to offer including the shopping, wineries, and forests. Tourists can also enjoy the city's temples, churches, and university setting. In Highland Mills, there are 7 hotels and other accommodations to choose from. Find out more about Highland Mills.
What are the top places to visit in Highland Mills?
Favorite places to visit include United States Military Academy, Palaia Vineyards Winery, and Schunnemunk State Park. You'll also find Woodbury Common Premium Outlets and Arrow Park Lake and Lodge in the area. Check out what more to see and do in Expedia's Highland Mills guide.
What's the weather like in Highland Mills?
The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Highland Mills are January, February, December, and March, with each month seeing an average of 6 inches of snowfall.