𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chester from RM349 (2026) - Fully Refundable Options

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Our top choices for Chester hotels

Hotel

Breakfast included

Pool

Reserve now, pay later

Bed & breakfast

A Holiday Inn Express hotel with a covered entrance, a parking lot, and a well-maintained lawn.

A buffet with labeled containers for omelets and other dishes.

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.

1. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

Sheridan

RM493

RM607 total

includes taxes & fees

30 Aug - 31 Aug

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

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

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

Elizabeth

RM868

RM982 total

includes taxes & fees

7 Sept - 8 Sept

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 room with a flat-screen TV, a fireplace, a desk with a computer, and comfortable seating.

A covered outdoor area with a fire pit, wooden chairs, and a view of a building with multiple windows.

A hotel entrance with stone pillars, a covered walkway, and a bench.

3. Sleep Inn & Suites Monroe - Woodbury

Monroe

Crysta

RM469

RM531 total

includes taxes & fees

30 Aug - 31 Aug

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.

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

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

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

4. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Leronda

RM541

RM666 total

includes taxes & fees

13 Sept - 14 Sept

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 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

Margaret

RM493

RM608 total

includes taxes & fees

30 Aug - 31 Aug

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.

6. LEGOLAND Hotel NEW York

Goshen

Dana

RM815

RM1,491 total

includes taxes & fees

7 Sept - 8 Sept

A multi-story hotel with a covered entrance, landscaped gardens, and a clear sky.

A lobby area with seating, a reception desk, and a beverage refrigerator.

A buffet with labeled containers of omelets and other breakfast items.

A modern hotel lobby with a central dining area, seating arrangements, and large windows offering views.

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

Middletown

Jade

RM493

RM582 total

includes taxes & fees

21 Sept - 22 Sept

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

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.

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

8. Courtyard by Marriott Middletown Goshen

Middletown

Henry

RM408

RM483 total

includes taxes & fees

30 Aug - 31 Aug

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

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

Middletown

Ju Hyun

RM502

RM592 total

includes taxes & fees

30 Aug - 31 Aug

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

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

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

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

10. Tru by Hilton Middletown

Middletown

siddhartha

RM414

RM489 total

includes taxes & fees

30 Aug - 31 Aug

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.

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

11. Comfort Suites Central Valley - Woodbury

Central Valley

Sarah

RM445

RM548 total

includes taxes & fees

30 Aug - 31 Aug

An outdoor seating area with a fire feature, wicker furniture, and a covered patio.

A multi-story hotel with a covered entrance and outdoor seating area.

A hotel room with a kitchenette, a sofa, a dining table, and a bed.

A modern lounge area with a sofa, tables, and chairs, featuring a 'HOME2' sign.

12. Home2 Suites by Hilton Middletown

Middletown

Carl

RM692

RM832 total

includes taxes & fees

20 Sept - 21 Sept

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

Barbara

RM443

RM523 total

includes taxes & fees

13 Sept - 14 Sept

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

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.

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

14. Hampton Inn & Suites Newburgh Stewart Airport

Newburgh

Vincent

RM493

RM583 total

includes taxes & fees

30 Aug - 31 Aug

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 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.

15. Hampton Inn by Hilton Middletown

Middletown

eliezer

RM394

RM466 total

includes taxes & fees

31 Aug - 1 Sept

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 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.

16. The Orange Inn Boutique Hotel

Goshen

Sarah

RM1,000

RM1,231 total

includes taxes & fees

25 Aug - 26 Aug

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 two beds, a desk, a chair, a TV, and a window with curtains.

An indoor swimming pool with clear water, a lifeguard chair, and a sign stating "No Diving Allowed".

17. Holiday Inn Express & Suites Montgomery by IHG

Montgomery

Chime

RM424

RM501 total

includes taxes & fees

30 Aug - 31 Aug

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

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

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

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

18. Microtel Inn & Suites by Wyndham Middletown

Middletown

Lisa

RM443

RM523 total

includes taxes & fees

25 Aug - 26 Aug

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

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

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

A reception desk with a blue wall and the text "Americas Best Value Inn".

19. Americas Best Value Inn at Central Valley-Woodbury

Central Valley

Marlon

RM400

RM492 total

includes taxes & fees

25 Aug - 26 Aug

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.

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

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

20. Residence Inn by Marriott Middletown Goshen

Middletown

Aaron

RM796

RM940 total

includes taxes & fees

30 Aug - 31 Aug

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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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent

"Clean room, friendly staff and great breakfasts"

Sleep Inn & Suites Monroe - Woodbury

8/10 Good

"Had a good experience. However, the elevator was out on Wednesday and all of us on the third floor. We are not young - 81 years old and many in the group have bad knees. Fortunately it was repaired when we returned that evening after attending a funeral."

Studio 6 Extended Stay Fishkill Westage Center NY

8/10 Good

"It was ok for the price."

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent

"Excellent location and stay"

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent

"nice place"

More cheap stays in Chester

Ramada by Wyndham Newburgh/West Point

1289 Route 300 Newburgh NY

RM309

RM365 total

31 Aug - 1 Sept

includes taxes & fees

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

915 Union Ave New Windsor NY

RM360

RM425 total

13 Sept - 14 Sept

includes taxes & fees

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

RM443

RM523 total

13 Sept - 14 Sept

includes taxes & fees

Sleep Inn & Suites Monroe - Woodbury

1 Sleep Way Monroe NY

RM469

RM531 total

30 Aug - 31 Aug

includes taxes & fees

9.4/10 Exceptional! (1,104 reviews)

Holiday Inn Express Hotel & Suites Chester by IHG

2 Bryle Place Chester NY

RM493

RM607 total

30 Aug - 31 Aug

includes taxes & fees

8.6/10 Excellent! (1,017 reviews)

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

RM614

RM756 total

24 Aug - 25 Aug

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 Crowne Plaza Suffern - Mahwah by IHG 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 20 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 RM349

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. Holiday Inn Express & Suites Middletown - Goshen by IHG

8. Courtyard by Marriott Middletown Goshen

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

10. Tru by Hilton Middletown

11. Comfort Suites Central Valley - Woodbury

12. Home2 Suites by Hilton Middletown

13. Sleep Inn & Suites Middletown - Goshen

14. Hampton Inn & Suites Newburgh Stewart Airport

15. Hampton Inn by Hilton Middletown

16. The Orange Inn Boutique Hotel

17. Holiday Inn Express & Suites Montgomery by IHG

18. Microtel Inn & Suites by Wyndham Middletown

19. Americas Best Value Inn at Central Valley-Woodbury

20. Residence Inn by Marriott Middletown Goshen

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Sleep Inn & Suites Monroe - Woodbury

Studio 6 Extended Stay Fishkill Westage Center NY

Holiday Inn Express Hotel & Suites Chester by IHG

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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Monroe - Woodbury

Holiday Inn Express Hotel & Suites Chester by IHG

Overlook Lodge at Bear Mountain

Frequently asked questions

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