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

This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Top 5 hotels in Chester at a glance

  1. Holiday Inn Express Hotel & Suites Chester by IHG — 2.5-star hotel in Chester. Guest rating: 8.6/10 — Excellent.
  2. The Dominion House Bed & Breakfast — 2-star hotel in Chester. Guest rating: 9.2/10 — Wonderful.
  3. Sleep Inn & Suites Monroe - Woodbury — 2.5-star hotel in Monroe. Guest rating: 9.4/10 — Exceptional.
  4. Fairfield Inn & Suites by Marriott Goshen Middletown — 3-star hotel in Goshen. Guest rating: 9.0/10 — Wonderful.
  5. Comfort Suites Central Valley - Woodbury — 2.5-star hotel in Central Valley. Guest rating: 8.4/10 — Very Good.

Where to stay in Chester?

Exterior

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.6 out of 10, Excellent, (1,025 reviews)
This conveniently located Chester hotel offers free perks including WiFi, parking, and weekday breakfast. Splash in the indoor pool after exploring nearby Woodbury Common Premium Outlets. Guests consistently praise the helpful staff and clean rooms.
The price is $119
$147 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express Hotel & Suites Chester by IHG
Exterior

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (235 reviews)
Unwind at this charming B&B with a refreshing outdoor pool, lush garden, and peaceful terrace. After complimentary breakfast, explore nearby hiking trails or head to LEGOLAND and Woodbury Common Premium Outlets, both within 15 minutes.
The price is $215
$243 total
includes taxes & fees
Aug 11 - Aug 12
The Dominion House Bed & Breakfast
Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,102 reviews)
Wake up to a complimentary breakfast at this Monroe hotel, just minutes from LEGOLAND® and premium shopping. The fitness center energizes your day while in-room refrigerators and microwaves offer convenience after exploring nearby Museum Village.
The price is $110
$125 total
includes taxes & fees
Aug 31 - Sep 1
Sleep Inn & Suites Monroe - Woodbury
Reception

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
9.0 out of 10, Wonderful, (1,008 reviews)
Wake up to a free breakfast at this Goshen hotel, just 5 minutes from LEGOLAND® New York. Cool off in the seasonal outdoor pool or maintain your routine at the 24-hour fitness center. Guests love the helpful staff and convenient free parking and WiFi.
The price is $134
$165 total
includes taxes & fees
Sep 1 - Sep 2
Fairfield Inn & Suites by Marriott Goshen Middletown
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (102 reviews)
The price is $104
$129 total
includes taxes & fees
Aug 30 - Aug 31
Comfort Suites Central Valley - Woodbury
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.4 out of 10, Very Good, (1,004 reviews)
This quiet Middletown hotel offers a seasonal outdoor pool and free breakfast just minutes from LEGOLAND® New York. Clean rooms provide comfort after visiting the Galleria at Crystal Run mall. With free WiFi and parking, plus fitness center access, guests praise the helpful staff.
The price is $98
$115 total
includes taxes & fees
Aug 17 - Aug 18
Hampton Inn by Hilton Middletown
Property amenity

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very Good, (1,004 reviews)
Enjoy American cuisine at The Bistro or unwind at the bar after exploring nearby LEGOLAND® and Galleria at Crystal Run. This Middletown hotel offers free WiFi, free parking, and is praised for its exceptionally helpful staff.
The price is $105
$125 total
includes taxes & fees
Aug 23 - Aug 24
Courtyard by Marriott Middletown Goshen
Exterior

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
2.5 star property
Middletown
8.8 out of 10, Excellent, (749 reviews)
Situated just minutes from LEGOLAND® New York and Galleria at Crystal Run, this hotel offers a refreshing indoor pool and fitness center. Enjoy complimentary breakfast, WiFi, and parking while the helpful staff ensures a pleasant stay in clean, business-friendly accommodations.
The price is $116
$137 total
includes taxes & fees
Aug 23 - Aug 24
Holiday Inn Express & Suites Middletown - Goshen by IHG
Free daily English breakfast

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,005 reviews)
Modern accommodations just minutes from LEGOLAND® New York. This hotel offers complimentary English breakfast, WiFi, and parking. Energize at the 24-hour fitness center or relax on the terrace after exploring nearby Orange County Fairgrounds.
The price is $103
$121 total
includes taxes & fees
Aug 16 - Aug 17
Tru by Hilton Middletown
Exterior

Parkway House Goshen Family-Friendly Bed & Breakfast

Parkway House Goshen Family-Friendly Bed & Breakfast
3.0 star property
Goshen
9.8 out of 10, Exceptional, (9 reviews)
The price is $130
$160 total
includes taxes & fees
Aug 6 - Aug 7
Parkway House Goshen Family-Friendly Bed & Breakfast
Lobby

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (1,007 reviews)
Discover serene comfort near LEGOLAND® New York at this Middletown gem. The indoor pool invites morning swims, while free breakfast, parking, and WiFi enhance your stay. Explore nearby restaurants or visit Galleria at Crystal Run after a peaceful night's rest.
The price is $124
$147 total
includes taxes & fees
Aug 16 - Aug 17
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Exterior

Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (126 reviews)
Warm, inviting atmosphere awaits at this Walden B&B where complimentary breakfast energizes your day. Explore nearby attractions with ease, knowing your car is safely parked in the free lot when you return to this cozy Hudson Valley haven.
The price is $104
$118 total
includes taxes & fees
Aug 5 - Aug 6
Tin Brook Bed & Breakfast
Free continental breakfast on weekdays

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,115 reviews)
Wake up to a complimentary breakfast before exploring nearby attractions like LEGOLAND® New York and Paramount Theatre. After sightseeing, enjoy a refreshing swim in the indoor pool or visit the 24-hour fitness center. Free WiFi and parking enhance your stay.
The price is $115
$136 total
includes taxes & fees
Sep 1 - Sep 2
Sleep Inn & Suites Middletown - Goshen
Exterior

Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown
2.0 star property
Middletown
7.0 out of 10, Good, (1,002 reviews)
Wake up refreshed at this welcoming Middletown hotel where complimentary continental breakfast jumpstarts your day. Just a short drive from LEGOLAND® New York and Galleria at Crystal Run, enjoy free WiFi and parking while helpful staff ensure a pleasant stay.
The price is $97
$114 total
includes taxes & fees
Sep 3 - Sep 4
Microtel Inn & Suites by Wyndham Middletown
Reception

The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (178 reviews)
Discover comfort at this Warwick hotel offering convenient amenities including complimentary WiFi and parking. The 24-hour front desk ensures round-the-clock assistance, while nearby attractions like Albert Wisner Memorial Library and Veteran's Memorial Park await exploration.
The price is $86
$97 total
includes taxes & fees
Aug 5 - Aug 6
The Hamlet Inn at Warwick
Lobby

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,128 reviews)
Wake up to a complimentary breakfast at this convenient hotel near shopping destinations. The indoor pool offers year-round relaxation after exploring nearby attractions. Rooms include refrigerators and microwaves, with free WiFi and parking completing your comfortable stay.
The price is $119
$146 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn Harriman Woodbury
Exterior

Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (71 reviews)
Set in Middletown, this hotel offers convenient access to LEGOLAND® New York and Galleria at Crystal Run. Just 28 minutes from Stewart Intl. Airport and 22 minutes from Harriman Station, it's perfectly positioned for regional exploration.
The price is $113
$133 total
includes taxes & fees
Aug 23 - Aug 24
Candlewood Suites Middletown Goshen by IHG
Exterior

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
2.5 star property
Montgomery
8.6 out of 10, Excellent, (900 reviews)
Near the train station, this Montgomery hotel offers convenience with a 24-hour health club and café. Free breakfast, WiFi and parking make stays stress-free. Close to City Winery Hudson Valley and only 16 minutes from Stewart Airport.
The price is $105
$119 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express & Suites Montgomery by IHG
Business center

Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
2.0 star property
Central Valley
7.2 out of 10, Good, (1,004 reviews)
Central Valley motel just 15 minutes from Woodbury Common Premium Outlets and LEGOLAND New York. Guests praise the helpful staff, clean rooms, and overall value. Enjoy complimentary WiFi and parking, plus easy access to Bear Mountain State Park and Old Glory Mall.
The price is $99
$122 total
includes taxes & fees
Aug 5 - Aug 6
Americas Best Value Inn at Central Valley-Woodbury
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (176 reviews)
Escape to this charming Victorian B&B in Montgomery, featuring a restaurant, snack bar, and serene garden terrace. Enjoy facials and complimentary breakfast before exploring nearby City Winery Hudson Valley and Orange County Farmers Museum.
The price is $121
$141 total
includes taxes & fees
Aug 5 - Aug 6
Borland House Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

When is the best time to visit Chester?

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 August
Currently viewing crowd sizes and weather for August.
Typical weather for Chester
August
High 28°C / low 18°C. Sunny most days.
View properties in August
28°
weather_sun
August, no crowd data, average high temperature 28 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
24°
weather_sun
September, no crowd data, average high temperature 24 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
17°
weather_sun
October, no crowd data, average high temperature 17 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
8°
10°
weather_partly_sunny
November, no crowd data, average high temperature 10 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
5°
ac_unit
December, no crowd data, average high temperature 5 degrees Celsius, average low temperature -2 degrees Celsius. Snow likely.
-2°
1°
ac_unit
January, no crowd data, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
3°
ac_unit
February, no crowd data, average high temperature 3 degrees Celsius, average low temperature -5 degrees Celsius. Snow likely.
-5°
8°
weather_partly_sunny
March, no crowd data, average high temperature 8 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
14°
weather_sun
April, no crowd data, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
5°
21°
weather_sun
May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
25°
weather_sun
June, no crowd data, average high temperature 25 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
29°
weather_sun
July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
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 Orange County Arboretum, both just a short drive away.
See properties

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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"Overlook lodge is a 5-minute drive away from the main historic inn building. Rooms themselves were clean, comfortable and well-maintained. There was a strong musty odor in the common room of the lodge but not in the room. While it was a pleasant setting in the woods, there was not much of an "overlook"."
Andrew 1-night trip
Posted 5 hours ago
Overlook Lodge at Bear Mountain

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 Sleep Inn & Suites Monroe - Woodbury.
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.