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Hotels in Chester

October 2026
3
November 2026

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Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Where to stay in Chester?

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 large white house with a porch, surrounded by trees and a stone wall.
A swimming pool with a deck, surrounded by potted plants and outdoor furniture.

1. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
$215
$243 total
includes taxes & fees
Oct 5 - Oct 6
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 hotel entrance with stone pillars, a covered walkway, and a bench.
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.

2. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
Monroe
$108
$122 total
includes taxes & fees
Nov 3 - Nov 4
Sleep Inn & Suites Monroe - Woodbury
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 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.

3. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
Goshen
$108
$259 total
includes taxes & fees
Oct 4 - Oct 5
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 spacious lobby with a stone accent wall, a flat-screen TV, and a seating area with sofas and a coffee table.
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.

4. 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 breakfast area with a counter displaying hard-boiled eggs, a bowl of green apples, and various pastries.
An outdoor seating area with a blue sofa, round table, and chairs, under a canopy with string lights.
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.

5. Tru by Hilton Middletown

Tru by Hilton Middletown
Middletown
$81
$96 total
includes taxes & fees
Nov 1 - Nov 2
Tru by Hilton Middletown
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 Courtyard by Marriott hotel with a sign, parking, and landscaped flower beds.

6. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
Middletown
$101
$119 total
includes taxes & fees
Oct 7 - Oct 8
Courtyard by Marriott Middletown Goshen
A lobby with a fireplace, seating area, and a reception desk.
A snack and beverage display in a store with various snacks, drinks, and a 'Welcome to Harriman Woodbury' sign.
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.

7. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
Central Valley
$114
$140 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Harriman Woodbury
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.
A vending machine area with two beverage dispensers and a snack shelf stocked with various products.
A hotel room with two beds, a desk, a TV, and a chair.
A gym with treadmills, a weight bench, and various exercise equipment.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
$114
$135 total
includes taxes & fees
Nov 1 - Nov 2
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Lobby
Breakfast area
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.

9. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
Central Valley
$112
$138 total
includes taxes & fees
Nov 2 - Nov 3
Comfort Suites Central Valley - Woodbury
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 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.

10. Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown
Middletown
$99
$116 total
includes taxes & fees
Nov 1 - Nov 2
Microtel Inn & Suites by Wyndham Middletown
A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.
An outdoor patio with a grill, chairs, and tables, featuring a red umbrella and string lights.
A modern restaurant with a central island, multiple tables, and chairs.
A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.

11. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
$155
$187 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites by Hilton Middletown
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 Sleep Inn & Suites hotel with a stone facade, multiple balconies, and a covered entrance.
A hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.

12. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown
$108
$128 total
includes taxes & fees
Nov 1 - Nov 2
Sleep Inn & Suites Middletown - Goshen
A hotel lobby with two sofas, a coffee machine, and a view of the parking lot.
A reception desk with a blue wall and the text "Americas Best Value Inn".
A hotel room with two beds, a nightstand, a lamp, and artwork on the walls.
A sign for Amerias Best Value Inn with a 'Welcome' sign above it.

13. 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 4 - Oct 5
Americas Best Value Inn at Central Valley-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 reception area with a counter, a clock, a no cash refunds sign, and a fire alarm.
A lobby with a red sofa, two lamps, a coffee table with flowers, and a wall art piece.
A Super 8 motel sign with a parking lot and a building in the background.

14. Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown
Middletown
$73
$86 total
includes taxes & fees
Nov 1 - Nov 2
Super 8 by Wyndham Middletown
A brick exterior with outdoor seating, tables covered with white tablecloths, and brick walls.
A hotel room with a large bed, a desk, a chair, and a TV.
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.

15. The Orange Inn Boutique Hotel

The Orange Inn Boutique Hotel
Goshen
$234
$288 total
includes taxes & fees
Oct 5 - Oct 6
The Orange Inn Boutique Hotel
A large, two-story house with a wrap-around porch and multiple chimneys.
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.
A spacious living room with a large sectional sofa, a wooden floor, and large windows offering views of the outdoors.

16. Parkway House Goshen Family-Friendly Bed & Breakfast

Parkway House Goshen Family-Friendly Bed & Breakfast
Goshen
$157
$194 total
includes taxes & fees
Oct 4 - Oct 5
Parkway House Goshen Family-Friendly Bed & Breakfast
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
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.
A hotel room with a sofa, a television on a wooden stand, a bed, and a view of the hallway.

17. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
Middletown
$89
$106 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn by Hilton Middletown
A modern room with a marble table and four purple chairs, a large window with blinds, and a framed picture on the wall.
A hotel room with two beds, a large mirror, and a framed picture on the wall.
A modern kitchen with a marble countertop and a dining area with a white table and purple chairs.
A building with a beige exterior, large windows, and a black door.

18. The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
Warwick
$86
$97 total
includes taxes & fees
Oct 4 - Oct 5
The Hamlet Inn at Warwick
A two-story house with a porch, a front door, and a small garden area with potted plants.
A sign for The Borland House, a bed and breakfast offering breakfast and brunch.
A grand hallway with a wooden staircase, a patterned carpet, and a dining area with chairs and a table.
A cozy living room with a sofa, armchair, and a table with a vase. A chandelier hangs from the ceiling, and there are framed pictures on the walls.

19. Borland House Inn

Borland House Inn
Montgomery
$114
$139 total
includes taxes & fees
Oct 5 - Oct 6
Borland House Inn
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A two-story building with a balcony, a car parked in front, and an American flag displayed.
A backyard with a grill and a fire pit.
A pond with a gazebo, surrounded by trees and a small building in the background.

20. High Point Motel

High Point Motel
Sussex
$92
$103 total
includes taxes & fees
Oct 4 - Oct 5
High Point Motel
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Go beyond your typical stay in Chester

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Spa
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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

October

High 17°C / low 8°C. Sunny most days.
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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

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

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
Goshen

10/10 Exceptional

United States
jonathan
Fairfield Inn & Suites by Marriott Goshen Middletown
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 large white house with a porch, surrounded by trees and a stone wall.
A swimming pool with a deck, surrounded by potted plants and outdoor furniture.

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester

10/10 Exceptional

United States
Cindy
The Dominion House Bed & Breakfast
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 Sleep Inn & Suites hotel with a stone facade, multiple balconies, and a covered entrance.
A hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown

10/10 Exceptional

United States
Damion
Sleep Inn & Suites Middletown - Goshen
A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.
An outdoor patio with a grill, chairs, and tables, featuring a red umbrella and string lights.
A modern restaurant with a central island, multiple tables, and chairs.
A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown

10/10 Exceptional

United States
Anonymous traveler
Home2 Suites by Hilton Middletown
A two-story house with a red front door, a chimney, and a well-maintained lawn.
A dining table set with glassware, a bowl of apples, a pumpkin, and a vase of flowers.
A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.
A room with a red sofa, a small table, and a bar area with stools.

Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
Monroe

10/10 Exceptional

United States
Alan
Villa Verde BB Greenwood Lake NY
A hotel lobby with two sofas, a coffee machine, and a view of the parking lot.
A reception desk with a blue wall and the text "Americas Best Value Inn".
A hotel room with two beds, a nightstand, a lamp, and artwork on the walls.
A sign for Amerias Best Value Inn with a 'Welcome' sign above it.

Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
Central Valley

10/10 Exceptional

United States
MIROSLAV
Americas Best Value Inn at Central Valley-Woodbury
A compact hotel room with two beds, a kitchenette, a dining area, and a view of a rocky landscape.
A backyard with a fire pit surrounded by red chairs, a picnic table, and a fence.
A cozy living room with a patterned armchair, a small table, and a black chair. There is a lamp on the table and a painting on the wall.
A covered outdoor area with benches, potted flowers, and a parking lot with vehicles.

Rolling Hills Motel

Rolling Hills Motel
Sussex

10/10 Exceptional

United States
Anonymous traveler
Rolling Hills Motel
A modern hotel room with a large bed, a sitting area with a sofa, a small table, a TV, and a bathtub.
A row of cylindrical planters with various plants and flowers.
A multi-story building with balconies, a covered outdoor seating area, and a well-lit entrance.
A living room with a fireplace, two grey sofas, a coffee table with candles, and a chandelier.

The Factory

The Factory
Beacon

10/10 Exceptional

United States
JAYANTI
The Factory
A hotel room with a large bed, a desk, a chair, a desk lamp, a wall-mounted TV, and a window with curtains.
A hotel entrance with stone pillars, a covered walkway, and a bench.
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.

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
Monroe

10/10 Exceptional

United States
Eileen
Sleep Inn & Suites Monroe - Woodbury
The exterior of The Inn and Spa at Beacon, featuring a black facade with gold lettering and large windows reflecting trees and lights.
A hotel entrance with a black door, a brick facade, and red flowers in front.
A living room with a fireplace, a sofa, a coffee table, and a view of the street through large windows.
A modern bedroom with a large bed, a sofa, a glass coffee table, a TV, and a shower area.

The Dutchess Inn and Spa at Beacon

The Dutchess Inn and Spa at Beacon
Beacon

10/10 Exceptional

United States
Marjorie
The Dutchess Inn and Spa at Beacon
A breakfast area with a counter displaying hard-boiled eggs, a bowl of green apples, and various pastries.
An outdoor seating area with a blue sofa, round table, and chairs, under a canopy with string lights.
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.

Tru by Hilton Middletown

Tru by Hilton Middletown
Middletown

10/10 Exceptional

United States
Daniela
Tru by Hilton Middletown
A historic stone building with arched windows and ivy-covered walls.
A garden with a central pond, surrounded by a stone pathway and lush greenery.
A spacious room with a large window, a plush sofa, a marble coffee table, and a classic wooden cabinet.
A formal garden with a central water feature, symmetrical seating arrangements, and lush greenery.

The Castle at Skylands Manor

The Castle at Skylands Manor
Ringwood

10/10 Exceptional

United States
glojo
The Castle at Skylands Manor
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 Courtyard by Marriott hotel with a sign, parking, and landscaped flower beds.

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
Middletown

10/10 Exceptional

United States
Kathleen
Courtyard by Marriott Middletown Goshen

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.