Chester Holiday Rentals, New York: Private House Rentals

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Our top choices for Chester hotels

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

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.

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

1. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

Sheila

2.625.192 ₫

3.232.269 ₫ total

includes taxes & fees

28 Sept - 29 Sept

A large, two-story white house with a wrap-around porch and a small front garden.

A traditional living room with a chandelier, vintage furniture, and a fireplace.

A large white house with a porch, surrounded by trees and a stone wall.

A garden with a stone fountain, a wooden gazebo, and various shrubs and flowers.

2. The Dominion House Bed & Breakfast

Chester

Sinead

5.588.280 ₫

6.321.774 ₫ total

includes taxes & fees

5 Oct - 6 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 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.

3. Sleep Inn & Suites Monroe - Woodbury

Monroe

John

2.807.136 ₫

3.175.571 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

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.

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

4. The Orange Inn Boutique Hotel

Goshen

DENISE

6.004.152 ₫

7.392.612 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

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

5. Hampton Inn Harriman Woodbury

Central Valley

3.175.703 ₫

3.910.083 ₫ total

includes taxes & fees

18 Oct - 19 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 Fairfield Inn & Suites hotel with a stone facade, a covered entrance, and a parking lot.

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

6. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Kelly

3.482.928 ₫

4.288.420 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

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

Middletown

Carlos

3.485.527 ₫

4.117.393 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A spacious conference room with a long table, multiple chairs, and a sofa area.

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

A hotel reception area with a counter, a framed picture, and a coffee station.

A hotel with a modern facade, a prominent entrance, and an American flag.

8. Hampton Inn & Suites Mahwah

Mahwah

Jagdeo

3.084.731 ₫

3.535.872 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A spacious lobby with a high ceiling, wooden beams, a central green wall with plants, seating areas, and a bar.

A spacious indoor area with multiple seating arrangements, including sofas and round tables, and a central decorative table with flowers.

A spacious atrium with a central water feature, multiple seating areas, and a bar.

A modern lobby with a fireplace, four armchairs, a coffee table, and a desk with a computer.

9. Crowne Plaza Suffern - Mahwah by IHG

Suffern

mary

3.067.056 ₫

3.569.285 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

An outdoor patio with a grill, chairs, and tables, featuring a red umbrella and string lights.

10. Home2 Suites by Hilton Middletown

Middletown

Carl

3.111.762 ₫

3.766.739 ₫ total

includes taxes & fees

26 Oct - 27 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.

11. Tru by Hilton Middletown

Middletown

Steve

2.770.747 ₫

3.272.945 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A hotel lobby with a reception desk, bar area, and a television displaying news.

A hotel room with a kitchenette, a living area with a sofa and a TV, and a large window with curtains.

A snack display area with various packaged snacks and a sign indicating 'TREATS'.

A Hampton Inn & Suites hotel with a modern facade, large windows, and a well-lit entrance.

12. Hampton Inn & Suites Newburgh Stewart Airport

Newburgh

Michael

3.815.106 ₫

4.506.593 ₫ 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.

13. Sleep Inn & Suites Middletown - Goshen

Middletown

Rebecca

2.878.823 ₫

3.400.610 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A hotel room with a sofa, a coffee table, a TV, a desk, and a bed.

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

A coffee station with two coffee machines and a variety of coffee pods and cups.

A coffee station with multiple coffee dispensers, a hot water station, and various coffee products on shelves.

14. Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Peekskill

Dexter

4.184.712 ₫

4.786.263 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

A spacious lobby with modern seating, a stone accent wall, and large windows offering views.

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

15. Residence Inn by Marriott Middletown Goshen

Middletown

jubert cruz

5.354.352 ₫

6.324.827 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A room with wooden paneling, a painting of a landscape, a clock, and a sofa with pillows.

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

16. High Point Motel

Sussex

Dakhil

2.391.264 ₫

2.669.248 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A spacious lobby with a high ceiling, a reception desk, a seating area with blue sofas and armchairs, and a visible Pepsi refrigerator.

A modern lounge area with a stone wall, a flat-screen TV, and blue seating.

An indoor swimming pool with a stone wall, blue chairs, and a lifeguard chair.

A modern breakfast bar with a wooden wall, a coffee machine, and a juice dispenser.

17. Comfort Suites Fishkill near Interstate 84

Fishkill

Daniel

2.780.364 ₫

3.214.796 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a green sofa, a small table, a bed with a headboard, a desk with a lamp, and a framed picture on the wall.

A spacious living area with sofas, a fireplace, and artwork on the walls.

A rack of black hexagonal dumbbells with visible weight markings, arranged on a metal stand in a gym setting.

A hotel with a covered entrance, multiple windows, and a sign that reads "Gold Award Winner."

18. Quality Inn & Suites Fishkill South near I-84

Fishkill

Israel

2.946.193 ₫

3.406.536 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

19. Courtyard by Marriott Middletown Goshen

Middletown

Harjeet

2.850.900 ₫

3.367.626 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.

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

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

20. Hampton Inn by Hilton Middletown

Middletown

ROBERT

2.645.500 ₫

3.124.996 ₫ total

includes taxes & fees

6 Oct - 7 Oct

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Stay near popular Chester attractions

The Rock Sports Complex

8.0/10 (18 reviews)

This dedicated sports venue hosts baseball and softball tournaments on well-maintained turf fields. Bring portable chairs and sun protection to enjoy the games in comfort at this local athletic hub.

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Museum Village

9.0/10 (8 reviews)

Step back in time at Museum Village, where costumed interpreters bring 19th-century rural American life to vivid reality. Explore historic buildings and watch traditional craftspeople demonstrate forgotten skills.

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Goosepond Mountain State Park

8.0/10 (5 reviews)

This 1,558-acre undeveloped park offers a tranquil escape with diverse trails through woods, fields, and wetlands. Bring binoculars to spot songbirds from the boardwalk that crosses marshy areas.

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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.

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Learn more about Chester

Lace up your hiking boots and hit the trails at Goosepond Mountain State Park for stunning views. After working up an appetite, head to Castle Fun Centre for go-karts, mini-golf, and arcade games.

See all hotels in Chester

A bridge with a plaque reading "City of Chester Queens Park Bridge 1923".

Top Chester Hotel Reviews

Hampton Inn & Suites Mahwah

10/10 Excellent

"Everything was good. Just stayed a night."

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent

"Easy to book. Amazing breakfast"

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent

"J’ai beaucoup aimé la piscine, le spa, le déjeuner complet et le café à disposition dans le hall d’entrée le personnel est très serviable, l’hôtel est propre et est à proximité des autoroutes"

Overlook Lodge at Bear Mountain

8/10 Good

"Every one is satisfactory."

Sonesta Simply Suites Nanuet

10/10 Excellent

"Best place to stay. All the staff are very friendly and go way and beyond."

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent

"I felt right at home! A quiet, very clean room with plenty of parking. Hotel is conveniently close to the highway entrance. I enjoyed my stay and the breakfast."

Hilton Garden Inn Nanuet

10/10 Excellent

"All"

The Thayer Hotel at West Point

8/10 Good

"Great stay, especially is you are visiting West Point in any capacity."

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent

"All great"

More cheap stays in Chester

Ramada by Wyndham Newburgh/West Point

1289 Route 300 Newburgh NY

2.079.360 ₫

2.456.244 ₫ total

5 Oct - 6 Oct

includes taxes & fees

4.8/10 (1,005 reviews)

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

915 Union Ave New Windsor NY

2.315.627 ₫

2.734.878 ₫ total

18 Oct - 19 Oct

includes taxes & fees

Comfort Suites Fishkill near Interstate 84

835 Route 52 Fishkill NY

2.780.364 ₫

3.214.796 ₫ total

25 Oct - 26 Oct

includes taxes & fees

Holiday Inn Express Hotel & Suites Chester by IHG

2 Bryle Place Chester NY

2.625.192 ₫

3.232.269 ₫ total

28 Sept - 29 Sept

includes taxes & fees

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

2.878.823 ₫

3.400.610 ₫ total

26 Oct - 27 Oct

includes taxes & fees

8.8/10 Excellent! (1,195 reviews)

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

2.965.038 ₫

3.650.702 ₫ total

27 Sept - 28 Sept

includes taxes & fees

Hotels in Chester with star rating

Frequently asked questions

What's the seasonal weather like in Chester?

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

Find hotels in Chester, NY from 2.400.977 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chester hotels

1. Holiday Inn Express Hotel & Suites Chester by IHG

2. The Dominion House Bed & Breakfast

3. Sleep Inn & Suites Monroe - Woodbury

4. The Orange Inn Boutique Hotel

5. Hampton Inn Harriman Woodbury

6. Fairfield Inn & Suites by Marriott Goshen Middletown

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

8. Hampton Inn & Suites Mahwah

9. Crowne Plaza Suffern - Mahwah by IHG

10. Home2 Suites by Hilton Middletown

11. Tru by Hilton Middletown

12. Hampton Inn & Suites Newburgh Stewart Airport

13. Sleep Inn & Suites Middletown - Goshen

14. Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

15. Residence Inn by Marriott Middletown Goshen

16. High Point Motel

17. Comfort Suites Fishkill near Interstate 84

18. Quality Inn & Suites Fishkill South near I-84

19. Courtyard by Marriott Middletown Goshen

20. Hampton Inn by Hilton Middletown

Stay near popular Chester attractions

The Rock Sports Complex

Museum Village

Goosepond Mountain State Park

Sugar Loaf Performing Arts Center

Learn more about Chester

Top Chester Hotel Reviews

Hampton Inn & Suites Mahwah

Sleep Inn & Suites Middletown - Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Overlook Lodge at Bear Mountain

Sonesta Simply Suites Nanuet

Sleep Inn & Suites Monroe - Woodbury

Hilton Garden Inn Nanuet

The Thayer Hotel at West Point

Crowne Plaza Suffern - Mahwah by IHG

More cheap stays in Chester

Ramada by Wyndham Newburgh/West Point

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

Comfort Suites Fishkill near Interstate 84

Holiday Inn Express Hotel & Suites Chester by IHG

Sleep Inn & Suites Middletown - Goshen

Overlook Lodge at Bear Mountain

Hotels in Chester with star rating

Frequently asked questions

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