Hotels in Chester

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Where to stay in Chester?

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

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

1. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

$107

$132 total

includes taxes & fees

Nov 18 - Nov 19

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

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

2. The Dominion House Bed & Breakfast

Chester

$108

$122 total

includes taxes & fees

Nov 9 - Nov 10

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

3. Sleep Inn & Suites Monroe - Woodbury

Monroe

$113

$127 total

includes taxes & fees

Nov 1 - Nov 2

A swimming pool with colorful umbrellas and lounge chairs.

A restaurant with multiple dining tables and chairs, a central counter with a chef figure, and colorful hanging lights.

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.

4. LEGOLAND Hotel NEW York

Goshen

$127

$281 total

includes taxes & fees

Oct 25 - Oct 26

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.

5. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

$129

$159 total

includes taxes & fees

Nov 1 - Nov 2

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.

6. Tru by Hilton Middletown

Middletown

$81

$96 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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.

7. Hampton Inn by Hilton Middletown

Middletown

$80

$94 total

includes taxes & fees

Nov 18 - Nov 19

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

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

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

An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.

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

Middletown

$118

$139 total

includes taxes & fees

Oct 25 - Oct 26

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

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

Middletown

$108

$128 total

includes taxes & fees

Nov 15 - Nov 16

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 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

$101

$119 total

includes taxes & fees

Nov 1 - Nov 2

A compact kitchen with a microwave, coffee maker, and refrigerator. There is a wooden shelf above the sink holding cups and glasses. A framed picture hangs on the wall, and a desk with a lamp is visible.

A swimming pool with four lounge chairs and a metal ladder.

A modern kitchen area with a coffee machine, a refrigerator stocked with beverages, and a coffee station with various coffee products.

A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.

11. Candlewood Suites Middletown Goshen by IHG

Middletown

$110

$130 total

includes taxes & fees

Oct 26 - Oct 27

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.

12. Comfort Suites Central Valley - Woodbury

Central Valley

$115

$142 total

includes taxes & fees

Nov 17 - Nov 18

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

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

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

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

13. Sleep Inn & Suites Middletown - Goshen

Middletown

$101

$119 total

includes taxes & fees

Nov 8 - Nov 9

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

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

14. Microtel Inn & Suites by Wyndham Middletown

Middletown

$94

$110 total

includes taxes & fees

Nov 15 - Nov 16

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 living room with a large sectional sofa, a fireplace, and a chandelier.

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

15. Parkway House Goshen Family-Friendly Bed & Breakfast

Goshen

$160

$197 total

includes taxes & fees

Oct 20 - Oct 21

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

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

16. Americas Best Value Inn at Central Valley-Woodbury

Central Valley

$99

$122 total

includes taxes & fees

Oct 20 - Oct 21

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

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

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.

17. Hampton Inn Harriman Woodbury

Central Valley

$118

$145 total

includes taxes & fees

Oct 26 - Oct 27

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

A hotel dining area with orange chairs and tables, a coffee station, and a wooden door.

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

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

18. Holiday Inn Express & Suites Montgomery by IHG

Montgomery

$118

$139 total

includes taxes & fees

Nov 15 - Nov 16

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

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

A multi-story hotel building with a prominent 'HOME 2' sign, featuring a modern brick facade and multiple windows.

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

19. Home2 Suites by Hilton Middletown

Middletown

$161

$193 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a bed, two bedside tables with lamps, a wall-mounted telephone, and a large black and white windmill painting.

A lobby with a red sofa, two lamps, a coffee table with flowers, and a wall art piece.

A reception area with a counter, a clock, a no cash refunds sign, and a fire alarm.

A kitchenette with a microwave, toaster, and coffee maker.

20. Super 8 by Wyndham Middletown

Middletown

$71

$83 total

includes taxes & fees

Nov 1 - Nov 2

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Go beyond your typical stay in Chester

Pet friendly

Pool

Apartment

Spa

Hot tub

Cottage

Family friendly

Our prices for hotels in Chester are cheapest in March

Top landmarks in Chester

The Rock Sports Complex

8.0/10 (18 reviews)

The Rock Sports Complex is 1.2 mi (2 km) from central Chester, why not stop by during your stay. If you like The Rock Sports Complex, you'll love Arrow Park Lake and Lodge and Warwick Township Veterans Memorial Park, both just a short drive away.

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Museum Village

9.0/10 (8 reviews)

Museum Village is 0.9 mi (1.5 km) from central Chester, why not stop by during your stay. If you want to experience more of the culture Chester has to offer, head to The Rock Sports Complex, Castle Fun Center, and LEGOLAND® New York.

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Goosepond Mountain State Park

8.0/10 (5 reviews)

Goosepond Mountain State Park is 2.1 mi (3.4 km) from central Chester, why not stop by during your stay.

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Sugar Loaf Performing Arts Center

If you're looking for things to do when staying in Sugar Loaf, go to Sugar Loaf Performing Arts Center. If you want to experience more of the culture Sugar Loaf has to offer, head to The Rock Sports Complex, Castle Fun Center, and LEGOLAND® New York.

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Learn more about Chester

Chester is applauded for its cultural attractions such as Museum Village and Sugar Loaf Performing Arts Center. Visitors to this family-friendly city speak highly of the restaurants whereas sights include Castle Fun Center and The Rock Sports Complex.

See all hotels in Chester

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

Check out reviews of Chester hotels guests love

Sonesta Simply Suites Nanuet

8/10 Good

"The staff have to really take a look at the bathroom in our suite -sink in rough shape, and all plumbing exposed - just looked awful."

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

8/10 Good

"Older hotel that needs to update for the travellers of today. no ports for charging electronics without a brick."

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent

"Immaculate property, friendly and accommodating staff, breakfast included and reasonable rate makes this inn my go to place to stay in the area."

Comfort Suites Fishkill near Interstate 84

10/10 Excellent

"Loved the room"

The Thayer Hotel at West Point

10/10 Excellent

"It is a true honor to stay at such a magnificent hotel with such a rich history. It would be fascinating to learn the unique story behind each room."

Ramada by Wyndham Newburgh/West Point

8/10 Good

"Fine basic motel. Lots of parking, easy access to highway, lots of places to eat nearby. Bed was very comfortable."

Overlook Lodge at Bear Mountain

10/10 Excellent

"Bear Mountain Inn is a unique and beautiful retreat in the heart of the Hudson Valley. We go for the scenery, hiking, and watching the marine and rail traffic along the Hudson River. Staff is always helpful. We booked 2 nights but could only. stay 1 due to a family emergency and the staff worked with Expedia to refund the 2nd night. Will definitely return as we love the atmosphere. Stayed in 1 of the stone cottages in the woods above the lake. Basic room with a shared common area and outdoor porch/deck. Room had a small refrigerator and TV with local channels. Clean and quiet and what you'd expect in a state or national park setting. Great 1.5 mile paved walking trail below the cottage that circles the picturesque lake on the property grounds. Nice way to start the day."

Frequently asked questions

What accommodations do travelers recommend in Chester?

Guests like Holiday Inn Express Hotel & Suites Chester by IHG, Sleep Inn & Suites Middletown - Goshen and La Quinta Inn & Suites by Wyndham Middletown-Goshen.

Can I book refundable hotels in Chester?

If you're looking for the flexibility to change your plans to Chester, most accommodations offer refundable* rates you can book. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.

Where should I consider staying in Chester if I'm looking for a budget-friendly accommodation?

An inexpensive option worth considering is Holiday Inn Express Hotel & Suites Chester by IHG.

Where can I stay in Chester if I want a vacation rental instead of a hotel?

Browse 11 vacation homes on our site.

What will the weather in Chester be like during my vacation?

July and August are typically the warmest months in Chester when the average temp is 70°F. January and February are the coldest months when the average temperature is 32°F. July and October are the months with the most rain.

Why should I book my Chester hotel with Hotels.com?

There are lots of reasons to book your Chester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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Book Hotels in Chester on Hotels.com

Hotels in Chester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Chester?

1. Holiday Inn Express Hotel & Suites Chester by IHG

2. The Dominion House Bed & Breakfast

3. Sleep Inn & Suites Monroe - Woodbury

4. LEGOLAND Hotel NEW York

5. Fairfield Inn & Suites by Marriott Goshen Middletown

6. Tru by Hilton Middletown

7. Hampton Inn by Hilton Middletown

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

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

10. Courtyard by Marriott Middletown Goshen

11. Candlewood Suites Middletown Goshen by IHG

12. Comfort Suites Central Valley - Woodbury

13. Sleep Inn & Suites Middletown - Goshen

14. Microtel Inn & Suites by Wyndham Middletown

15. Parkway House Goshen Family-Friendly Bed & Breakfast

16. Americas Best Value Inn at Central Valley-Woodbury

17. Hampton Inn Harriman Woodbury

18. Holiday Inn Express & Suites Montgomery by IHG

19. Home2 Suites by Hilton Middletown

20. Super 8 by Wyndham Middletown

Go beyond your typical stay in Chester

Price trends for hotels in Chester

Typical weather for Chester

Top landmarks in Chester

The Rock Sports Complex

Museum Village

Goosepond Mountain State Park

Sugar Loaf Performing Arts Center

Learn more about Chester

Check out reviews of Chester hotels guests love

Sonesta Simply Suites Nanuet

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

Sleep Inn & Suites Middletown - Goshen

Comfort Suites Fishkill near Interstate 84

The Thayer Hotel at West Point

Ramada by Wyndham Newburgh/West Point

Overlook Lodge at Bear Mountain

Frequently asked questions

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