𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chester from RM326 (2026) - Fully Refundable Options

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Our top choices for Chester 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 hotel lobby with a large map mural, seating areas, and a reception desk.

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

1. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

Sheila

RM400

RM493 total

includes taxes & fees

12 Oct - 13 Oct

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

A swimming pool with a deck, surrounded by potted plants and outdoor furniture.

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.

2. The Dominion House Bed & Breakfast

Chester

Sinead

RM878

RM994 total

includes taxes & fees

12 Oct - 13 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 covered outdoor area with a fire pit, wooden chairs, and a view of a building with multiple windows.

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

RM448

RM507 total

includes taxes & fees

27 Oct - 28 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 Fairfield Inn & Suites hotel with a stone facade, a covered entrance, and a parking lot.

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

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

4. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Aeron

RM527

RM649 total

includes taxes & fees

1 Nov - 2 Nov

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

John

RM483

RM594 total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with colorful umbrellas and lounge chairs.

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

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.

6. LEGOLAND Hotel NEW York

Goshen

Kylaia

RM442

RM1,057 total

includes taxes & fees

12 Oct - 13 Oct

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

A modern lounge area with seating, tables, and hanging chairs.

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

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

7. Tru by Hilton Middletown

Middletown

Steve

RM332

RM392 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 modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

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.

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

Middletown

Carlos

RM462

RM546 total

includes taxes & fees

3 Nov - 4 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 hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.

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

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

Middletown

Mignonne

RM470

RM555 total

includes taxes & fees

4 Nov - 5 Nov

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 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.

10. Courtyard by Marriott Middletown Goshen

Middletown

Kim

RM413

RM488 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

11. The Orange Inn Boutique Hotel

Goshen

DENISE

RM944

RM1,162 total

includes taxes & fees

12 Oct - 13 Oct

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

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

12. Home2 Suites by Hilton Middletown

Middletown

Carl

RM656

RM790 total

includes taxes & fees

26 Oct - 27 Oct

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

A modern lobby with a brown sofa, yellow armchairs, a patterned carpet, and a decorative plant centerpiece.

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.

13. Sleep Inn & Suites Middletown - Goshen

Middletown

Mark

RM417

RM492 total

includes taxes & fees

1 Nov - 2 Nov

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

14. Residence Inn by Marriott Middletown Goshen

Middletown

jubert cruz

RM768

RM907 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

15. Hampton Inn by Hilton Middletown

Middletown

Myung

RM379

RM447 total

includes taxes & fees

2 Nov - 3 Nov

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

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

16. Comfort Suites Central Valley - Woodbury

Central Valley

Vu andyvu

RM482

RM593 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

17. Microtel Inn & Suites by Wyndham Middletown

Middletown

sunil

RM389

RM459 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A hotel reception desk with a large 'happy.' poster on the wall, a counter with a computer, and a display of brochures.

18. Hampton Inn & Suites Newburgh Stewart Airport

Newburgh

Sharon

RM566

RM669 total

includes taxes & fees

29 Oct - 30 Oct

A Holiday Inn Express & Suites building with a covered entrance, stone facade, and a parking area with a bench.

A reception area with a modern design, featuring a large abstract wall art, a seating area with a bench, and a potted plant.

A hotel room with a bed, a desk, a sofa, a coffee machine, and a microwave.

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

19. Holiday Inn Express & Suites Montgomery by IHG

Montgomery

Darwin

RM527

RM623 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

20. Homewood Suites Stewart Airport

New Windsor

Tonia

RM622

RM735 total

includes taxes & fees

1 Nov - 2 Nov

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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

The Thayer Hotel at West Point

10/10 Excellent

"非常棒的一个古老的酒店，如果你想逛西点军校，那就太方便了。酒店就在Hudson 河边，景色秀美，酒店入住客人素质很高，非常安静整洁。去奥特莱斯买买买也非常方便，下次还来住。"

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent

"X"

Comfort Suites Fishkill near Interstate 84

8/10 Good

"a comfortable stay at a clean hotel."

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent

"😊"

Inn on the Hudson

10/10 Excellent

"This is my fourth visit to this location, and I plan to continue staying here in the future. The scenery is beautiful, the rooms are clean, the staff is wonderful, and everything is perfect."

Ramada by Wyndham Newburgh/West Point

10/10 Excellent

"Very accommodating staff, they were able to move me to a room that didn't require stairs because I had a rolling cart with gear I needed to bring inside each night. I had to add a night to my reservation, so I bought another night there on Hotels.com, and they simply kept me in my same room so I didn't need to move anything. It was great! Good coffee available in the morning, easy location to get in and out of. They were actively renovating the property while I was there, so I don't count that towards the cleanliness of the property; everything was very clean, even while under renovation. Will stay again when needed!"

Studio 6 Extended Stay Fishkill Westage Center NY

10/10 Excellent

"Wonderful staff"

More cheap stays in Chester

Ramada by Wyndham Newburgh/West Point

1289 Route 300 Newburgh NY

RM276

RM326 total

14 Oct - 15 Oct

includes taxes & fees

4.8/10 (1,000 reviews)

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

RM356

RM420 total

3 Nov - 4 Nov

includes taxes & fees

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

915 Union Ave New Windsor NY

RM364

RM430 total

25 Oct - 26 Oct

includes taxes & fees

Comfort Suites Fishkill near Interstate 84

835 Route 52 Fishkill NY

RM399

RM462 total

2 Nov - 3 Nov

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

RM417

RM492 total

1 Nov - 2 Nov

includes taxes & fees

8.8/10 Excellent! (1,219 reviews)

Holiday Inn Express Hotel & Suites Chester by IHG

2 Bryle Place Chester NY

RM400

RM493 total

12 Oct - 13 Oct

includes taxes & fees

Frequently asked questions

What's the best place to stay in Chester?

Based on our traveller data, Holiday Inn Express Hotel & Suites Chester by IHG is one of the top choices for your stay. This hotel offers free breakfast and an indoor pool. Other good choices for your stay in the area are Overlook Lodge at Bear Mountain and Sleep Inn & Suites Middletown - Goshen. See all available top hotels, or vacation rentals in Chester.

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

Yes! You'll find that most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What's the best family accommodation in Chester?

The Dominion House Bed & Breakfast is a B&B with an outdoor pool and free parking, and it's a top choice on Expedia for families. Also, children of all ages will enjoy a visit to Castle Fun Center. Find more child-friendly accommodations in Chester.

What is the favourite LGBTQ-friendly accommodation in Chester?

Holiday Inn Express Hotel & Suites Chester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free Wi-Fi. The Dominion House Bed & Breakfast is another good option for your trip. See all available hotels listed as LGBTQ-friendly in Chester.

What are some accommodation options with pools in Chester?

Holiday Inn Express Hotel & Suites Chester by IHG is a top hotel with a pool, free on-the-go breakfast and free WiFi. View all hotels with pools in Chester.

What is staying in Chester like?

Visitors to Chester will definitely enjoy the shopping and restaurants. Tourists can also enjoy the city's ski areas and coffee shops. A top sight in the area is Woodbury Common Premium Outlets. In Chester, there are 21 hotels and other accommodation options to choose from. Find out more about Chester.

What are the top places to visit in Chester?

Cultural venues include Museum Village and 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 Chester guide.

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.

Chester hotels from RM326

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. Fairfield Inn & Suites by Marriott Goshen Middletown

5. Hampton Inn Harriman Woodbury

6. LEGOLAND Hotel NEW York

7. Tru by Hilton Middletown

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

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

10. Courtyard by Marriott Middletown Goshen

11. The Orange Inn Boutique Hotel

12. Home2 Suites by Hilton Middletown

13. Sleep Inn & Suites Middletown - Goshen

14. Residence Inn by Marriott Middletown Goshen

15. Hampton Inn by Hilton Middletown

16. Comfort Suites Central Valley - Woodbury

17. Microtel Inn & Suites by Wyndham Middletown

18. Hampton Inn & Suites Newburgh Stewart Airport

19. Holiday Inn Express & Suites Montgomery by IHG

20. Homewood Suites Stewart Airport

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

The Thayer Hotel at West Point

Sleep Inn & Suites Middletown - Goshen

Comfort Suites Fishkill near Interstate 84

DoubleTree by Hilton Hotel Nanuet

Inn on the Hudson

Ramada by Wyndham Newburgh/West Point

Studio 6 Extended Stay Fishkill Westage Center NY

More cheap stays in Chester

Ramada by Wyndham Newburgh/West Point

Overlook Lodge at Bear Mountain

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

Comfort Suites Fishkill near Interstate 84

Sleep Inn & Suites Middletown - Goshen

Holiday Inn Express Hotel & Suites Chester by IHG

Frequently asked questions

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