Hotels in Chester

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Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Where to stay in Chester?

A hotel with a central entrance pavilion, a flag, and a landscaped garden.
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.
A modern hotel lobby with a large map mural, seating areas, and a reception desk.

1. Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
Chester
$107
$132 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Hotel & Suites Chester by IHG
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

The Dominion House Bed & Breakfast
Chester
$108
$122 total
includes taxes & fees
Nov 9 - Nov 10
The Dominion House Bed & Breakfast
A hotel room with a large bed, a desk, a chair, a desk lamp, a wall-mounted TV, and a window with curtains.
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.
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

Sleep Inn & Suites Monroe - Woodbury
Monroe
$113
$127 total
includes taxes & fees
Nov 1 - Nov 2
Sleep Inn & Suites Monroe - Woodbury
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 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.

4. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
Goshen
$127
$281 total
includes taxes & fees
Oct 25 - Oct 26
LEGOLAND Hotel NEW York
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.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.

5. Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
Goshen
$129
$159 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Goshen Middletown
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 modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.
A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.

6. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
Middletown
$80
$94 total
includes taxes & fees
Nov 18 - Nov 19
Hampton Inn by Hilton Middletown
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 gym with treadmills, a weight bench, and various exercise equipment.
A vending machine area with two beverage dispensers and a snack shelf stocked with various products.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
$108
$128 total
includes taxes & fees
Nov 15 - Nov 16
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.
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.
A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.

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

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown
$114
$135 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express & Suites Middletown - Goshen by IHG
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 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.

9. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
Middletown
$101
$119 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Middletown Goshen
A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.
A modern kitchen area with a coffee machine, a refrigerator stocked with beverages, and a coffee station with various coffee products.
A swimming pool with four lounge chairs and a metal ladder.
A circular outdoor seating area with a fire pit in the center, surrounded by wicker chairs and a small table.

10. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
Middletown
$110
$130 total
includes taxes & fees
Oct 26 - Oct 27
Candlewood Suites Middletown Goshen by IHG
Lobby
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 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.
Breakfast area

11. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
Central Valley
$115
$142 total
includes taxes & fees
Nov 17 - Nov 18
Comfort Suites Central Valley - Woodbury
A multi-story hotel with a central courtyard, large windows, and a parking lot.
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.
A lobby with a stone fireplace, seating area, and a reception desk.

12. Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown
Middletown
$94
$111 total
includes taxes & fees
Nov 8 - Nov 9
Microtel Inn & Suites by Wyndham Middletown
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.
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

Sleep Inn & Suites Middletown - Goshen
Middletown
$101
$119 total
includes taxes & fees
Nov 8 - Nov 9
Sleep Inn & Suites Middletown - Goshen
A hotel lobby with two sofas, a coffee machine, and a view of the parking lot.
A sign for Amerias Best Value Inn with a 'Welcome' sign above it.
A reception desk with a blue wall and the text "Americas Best Value Inn".
A lobby with a reception desk, a sofa, a coffee table, and a dining area with chairs and a table.

14. Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
Central Valley
$99
$122 total
includes taxes & fees
Oct 19 - Oct 20
Americas Best Value Inn at Central Valley-Woodbury
A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.
A multi-story hotel building with a prominent 'HOME 2' sign, featuring a modern brick facade and multiple windows.
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.

15. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
$161
$193 total
includes taxes & fees
Oct 26 - Oct 27
Home2 Suites by Hilton Middletown
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.

16. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
Central Valley
$118
$145 total
includes taxes & fees
Oct 26 - Oct 27
Hampton Inn Harriman Woodbury
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 Super 8 motel sign with a parking lot and a building in the background.

17. Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown
Middletown
$71
$83 total
includes taxes & fees
Nov 1 - Nov 2
Super 8 by Wyndham Middletown
A Holiday Inn Express & Suites building with a covered entrance, stone facade, and a parking area with a bench.
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.
A hotel room with a bed, a desk, a sofa, a coffee machine, and a microwave.

18. Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
Montgomery
$112
$132 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express & Suites Montgomery by IHG
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 hotel room with a large bed, a desk, a chair, and a TV.
A multi-story hotel with balconies, outdoor seating, and a well-lit facade.

19. The Orange Inn Boutique Hotel

The Orange Inn Boutique Hotel
Goshen
$275
$339 total
includes taxes & fees
Oct 29 - Oct 30
The Orange Inn Boutique Hotel
A rectangular swimming pool with a wooden deck and a fence.
A Days Inn with a prominent sign, multiple motel units, and a well-maintained lawn.
A lobby with a reception desk, a Coca-Cola refrigerator, a Day's Inn sign, and a seating area with a chair and table.
A hotel room with a desk, television, two beds, a chair, and a window with curtains.

20. Days Inn by Wyndham Middletown

Days Inn by Wyndham Middletown
New Hampton
$77
$90 total
includes taxes & fees
Nov 1 - Nov 2
Days Inn by Wyndham Middletown
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Our prices for hotels in Chester are cheapest in March
Price trends for hotels in Chester
Pricing is based on two traveler single night rates
View properties in October
Typical weather for Chester
October
High 17°C / low 8°C. Sunny most days.
View properties in October
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14°
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Monthly weather averages (˚C)

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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

8/10 Good
"Great stay"
Justine 1-night trip
Posted 2 hours ago
Sleep Inn & Suites Middletown - Goshen
Days Inn by Wyndham Nanuet / Spring Valley

Days Inn by Wyndham Nanuet / Spring Valley

10/10 Excellent
"Amazing serious and professional staff from the front desk, Maintanance, Mattie and all the well behaved guests who stayed. I was surprised they had a quick grab and go station with coffee, juice, morning sugar and needed calories to go. Also while the laundry room just like 3535 Chain Bridge Rd, 22033 easy to pay with quarters and go. The inside of the machines while small are good working conditions and exactly what is needed for a short and or longer stay. Unexpected, management took me in right away without any problems and have been extremely professional. The Colombian restaurant, EN BARANQUILLA ME QUEDÓ, GOTAS d LLUVIA, OIGA, MIREÉ, VEA Q EN CALI NO FANTAZMEANNN…con EÑ TORO y vasos d colores! TOY WIZ, BAGEL BOY, QUICK CHECK & all the great walking distances shops makes this A GREAT PLACE TO STAY."
Eric 5-night trip
Posted 1 day ago
Days Inn by Wyndham Nanuet / Spring Valley
Overlook Lodge at Bear Mountain

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."
Robert K 2-night trip
Posted 2 days ago
Overlook Lodge at Bear Mountain
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

10/10 Excellent
"Convenient location, clean & comfortable room, and great food with the I-84 Diner across the parking lot."
Eric 3-night trip
Posted 2 days ago
Comfort Suites Fishkill near Interstate 84

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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