Sugar Loaf Holiday Rentals, Chester: Private House Rentals

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Our top choices for Sugar Loaf hotels

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

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

A modern dining area with blue upholstered chairs and a wooden table. There is a kitchen area visible through an open doorway.

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

1. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

Stephanie

฿3,730

฿4,593 total

includes taxes & fees

18 Nov - 19 Nov

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

A modern hotel lobby with seating areas, a bar, and a television screen.

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

Natasha

฿3,781

฿4,277 total

includes taxes & fees

1 Nov - 2 Nov

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 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.

A Fairfield Inn & Suites hotel with a stone facade, a covered entrance, and a parking lot.

3. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Aeron

฿4,332

฿5,334 total

includes taxes & fees

3 Nov - 4 Nov

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

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

A hotel room with a large bed, a sofa, a desk, and a bathroom.

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

4. Hampton Inn Harriman Woodbury

Central Valley

Timothy

฿3,971

฿4,889 total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with colorful umbrellas and lounge chairs.

A bar area with a long counter, multiple hanging lights, and a variety of bottles.

A colorful play area with a check-in counter and a mascot.

A hotel room with a large bed, a bookshelf, a mural, and a window with curtains.

5. LEGOLAND Hotel NEW York

Goshen

Kylaia

฿4,280

฿9,457 total

includes taxes & fees

1 Nov - 2 Nov

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 vending machine area with two beverage dispensers and a snack shelf stocked with various products.

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

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

Middletown

Marvin

฿3,657

฿4,319 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

7. Tru by Hilton Middletown

Middletown

Barry

฿2,728

฿3,223 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a kitchenette, including a microwave, coffee maker, and sink.

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

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

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

8. Home2 Suites by Hilton Middletown

Middletown

Carl

฿5,395

฿6,491 total

includes taxes & fees

27 Oct - 28 Oct

A spacious living area with a blue sofa, yellow armchair, and a coffee table. There is a TV mounted on a wooden shelf, and a kitchen area is visible in the background.

A hotel with a brick facade, a covered entrance, and a sign indicating it is a Comfort Suites hotel.

A modern hotel room with a kitchenette, a bed with white bedding, a seating area with a yellow ottoman, and a large window with curtains.

9. Comfort Suites Central Valley - Woodbury

Central Valley

Vu andyvu

฿3,959

฿4,875 total

includes taxes & fees

19 Nov - 20 Nov

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

A Courtyard by Marriott hotel with a sign, parking, and landscaped flower beds.

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

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

10. Courtyard by Marriott Middletown Goshen

Middletown

marc

฿3,399

฿4,016 total

includes taxes & fees

8 Nov - 9 Nov

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

A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.

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.

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

Middletown

Mignonne

฿3,966

฿4,685 total

includes taxes & fees

25 Oct - 26 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 hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.

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

12. Sleep Inn & Suites Middletown - Goshen

Middletown

Justine

฿3,399

฿4,016 total

includes taxes & fees

10 Nov - 11 Nov

An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.

A modern bar area with a stone accent wall, a long wooden bar counter, and a flat-screen TV mounted above the bar.

An indoor swimming pool with clear water, surrounded by grey tiled flooring and walls, large windows offering views of the outside, and a lifeguard station with a ladder.

A spacious living area with a stone wall, a flat-screen TV, comfortable seating, and a modern chandelier.

13. Residence Inn by Marriott Middletown Goshen

Middletown

jubert cruz

฿6,318

฿7,463 total

includes taxes & fees

8 Nov - 9 Nov

A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

A gym with exercise equipment, treadmills, and weight machines.

A modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.

A hotel room with a sofa, a television on a wooden stand, a bed, and a view of the hallway.

14. Hampton Inn by Hilton Middletown

Middletown

Amanda

฿2,685

฿3,172 total

includes taxes & fees

19 Nov - 20 Nov

A hotel lobby with two sofas, a coffee machine, and a view of the parking lot.

A lobby with a reception desk, a sofa, a coffee table, and a dining area with chairs and a table.

A hotel room with two beds, a nightstand, a lamp, and artwork on the walls.

A sign for Amerias Best Value Inn with a 'Welcome' sign above it.

15. Americas Best Value Inn at Central Valley-Woodbury

Central Valley

Marlon

฿3,327

฿4,096 total

includes taxes & fees

25 Oct - 26 Oct

A Hampton Inn & Suites by Hilton hotel with a large illuminated sign, modern architecture, and a well-lit facade.

A modern kitchen area with wooden cabinets, a coffee station, and a tiled floor.

A gym with treadmills, elliptical machines, and a large window with a view of buildings.

A store interior with shelves stocked with various snacks and treats, a chalkboard with a message, and a wall with a circular design.

16. Hampton Inn & Suites Newburgh Stewart Airport

Newburgh

Manus

฿4,828

฿5,703 total

includes taxes & fees

28 Oct - 29 Oct

A multi-story hotel with a central courtyard, large windows, and a parking lot.

A hotel room with a bed, a desk, a chair, a wardrobe, and a bathroom mirror.

A modern dining area with long tables and chairs, a bar area with a TV, and a kitchen in the background.

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

17. Microtel Inn & Suites by Wyndham Middletown

Middletown

Peggy

฿3,142

฿3,712 total

includes taxes & fees

15 Nov - 16 Nov

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 hotel room with a large bed, a desk, a chair, and a TV.

18. The Orange Inn Boutique Hotel

Goshen

DENISE

฿8,041

฿9,900 total

includes taxes & fees

29 Oct - 30 Oct

A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.

A spacious hotel lobby with a large dining table, comfortable seating, and ceiling fans.

A spacious living area with a curved sofa, a fireplace, and a modern chandelier.

A multi-story hotel with a prominent entrance, stone pillars, and a well-maintained lawn.

19. Homewood Suites Stewart Airport

New Windsor

Tonia

฿5,113

฿6,040 total

includes taxes & fees

1 Nov - 2 Nov

A large, two-story house with a wrap-around porch and multiple chimneys.

A spacious living room with a large sectional sofa, a wooden floor, and large windows offering views of the outdoors.

A spacious dining area with a large table and chairs, surrounded by large windows offering views of a residential neighborhood.

A buffet setup with various food items and a decorative centerpiece.

20. Parkway House Goshen Family-Friendly Bed & Breakfast

Goshen

Aakif

฿4,030

฿4,962 total

includes taxes & fees

22 Oct - 23 Oct

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Stay near popular Sugar Loaf attractions

Sugar Loaf Performing Arts Center

You can make plans for a show at Sugar Loaf Performing Arts Center during your trip to Sugar Loaf. Make some time to visit the shops while you're in the area.

See properties

Top Sugar Loaf Hotel Reviews

Inn on the Hudson

8/10 Good

"Slightly dated hotel walkable into the town centre have used before and would use again"

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

8/10 Good

"I needed a rack and got one."

Comfort Suites Central Valley - Woodbury

8/10 Good

"Only 1 sheet for pull out bed. Toilet seat was very loose. Common issue with hotel showers is access to turn on shower is on the sealed side of shower so have to get in in order to adjust water temperature. Hotel was very clean."

Crowne Plaza Suffern - Mahwah by IHG

8/10 Good

"They have begun to charge $10 to park on the property which is kind of ridiculous , not to many happy guests with the new policy."

Hampton Inn Harriman Woodbury

10/10 Excellent

"The room was clean and spacious. Staff were extra helpful and ready to assist. They were friendly and engaging. The view from my window was amazing - perfect to catch the fall foliage. I liked that there was a free shuttle to get my guests and I to the closest places such as the bus stop and Woodbury Commons Outlets since we didn’t drive there. The breakfast was amazing with a good variety. The gym and heated pool were a bonus. My guests and I are looking forward to staying again to take full use of the amenities and enjoy such great hospitality and service again!"

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent

"Very clean and quiet. Definitely a top choice."

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

10/10 Excellent

"Staff was polite and helpful"

Hampton Inn & Suites Mahwah

8/10 Good

"I thought it was very helpful that they had breakfast bags to go for those of us that couldn't get to the breakfast."

Ramada by Wyndham Newburgh/West Point

8/10 Good

"Was under construction, room was clean and comfortable."

More cheap stays in Sugar Loaf

Ramada by Wyndham Newburgh/West Point

1289 Route 300 Newburgh NY

฿2,146

฿2,536 total

25 Oct - 26 Oct

includes taxes & fees

4.8/10 (1,001 reviews)

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

915 Union Ave New Windsor NY

฿2,994

฿3,536 total

8 Nov - 9 Nov

includes taxes & fees

8.4/10 Very good! (1,007 reviews)

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

฿3,399

฿4,016 total

10 Nov - 11 Nov

includes taxes & fees

Holiday Inn Express Ramsey-Mahwah by IHG

946 Route 17 North Ramsey NJ

฿3,694

฿4,235 total

25 Oct - 26 Oct

includes taxes & fees

9.2/10 Wonderful! (1,003 reviews)

Holiday Inn Express Hotel & Suites Chester by IHG

2 Bryle Place Chester NY

฿3,730

฿4,593 total

18 Nov - 19 Nov

includes taxes & fees

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

฿3,899

฿4,606 total

3 Nov - 4 Nov

includes taxes & fees

Frequently asked questions

What's the best place to stay in Sugar Loaf?

Overlook Lodge at Bear Mountain, located 15.3 mi (24.6 km) from the heart of Sugar Loaf, is a top choice for your stay, based on our traveller data. Other good options for your visit to the area are Sleep Inn & Suites Middletown - Goshen and Crowne Plaza Suffern - Mahwah by IHG. See all available top hotels, or vacation rentals in Sugar Loaf.

If I need to cancel my hotel reservation in Sugar Loaf, will I receive a refund?

Yes, you'll find most room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you booked a non-refundable reservation, you might still have the option to cancel and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Sugar Loaf.

What is staying in Sugar Loaf like?

Visitors can enjoy all that Sugar Loaf has to offer, including the shopping and restaurants. A top sight in the area is Woodbury Common Premium Outlets. In Sugar Loaf, there are 3 hotels and other accommodation options to choose from. Find out more about Sugar Loaf.

What is there to see in Sugar Loaf?

A favourite place to visit is Sugar Loaf Performing Arts Center. Additionally, you'll find Woodbury Common Premium Outlets in the area. Take a look at what more there is to see and do in Expedia's Sugar Loaf guide.

What's the weather like in Sugar Loaf?

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 Sugar Loaf are January, February, March and April, with each month seeing an average of 16 cm of snowfall.

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More ways to book

Book Hotels in Sugar Loaf on Expedia.com

Find hotels in Sugar Loaf, NY from ฿2,536

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Sugar Loaf

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Sugar Loaf hotels

1. Holiday Inn Express Hotel & Suites Chester by IHG

2. Sleep Inn & Suites Monroe - Woodbury

3. Fairfield Inn & Suites by Marriott Goshen Middletown

4. Hampton Inn Harriman Woodbury

5. LEGOLAND Hotel NEW York

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

7. Tru by Hilton Middletown

8. Home2 Suites by Hilton Middletown

9. Comfort Suites Central Valley - Woodbury

10. Courtyard by Marriott Middletown Goshen

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

12. Sleep Inn & Suites Middletown - Goshen

13. Residence Inn by Marriott Middletown Goshen

14. Hampton Inn by Hilton Middletown

15. Americas Best Value Inn at Central Valley-Woodbury

16. Hampton Inn & Suites Newburgh Stewart Airport

17. Microtel Inn & Suites by Wyndham Middletown

18. The Orange Inn Boutique Hotel

19. Homewood Suites Stewart Airport

20. Parkway House Goshen Family-Friendly Bed & Breakfast

Stay near popular Sugar Loaf attractions

Sugar Loaf Performing Arts Center

Top Sugar Loaf Hotel Reviews

Inn on the Hudson

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Comfort Suites Central Valley - Woodbury

Crowne Plaza Suffern - Mahwah by IHG

Hampton Inn Harriman Woodbury

Sleep Inn & Suites Monroe - Woodbury

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

Hampton Inn & Suites Mahwah

Ramada by Wyndham Newburgh/West Point

More cheap stays in Sugar Loaf

Ramada by Wyndham Newburgh/West Point

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

Sleep Inn & Suites Middletown - Goshen

Holiday Inn Express Ramsey-Mahwah by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

Overlook Lodge at Bear Mountain

Frequently asked questions

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