Hotels in Chester, NY

12 available hotel offers

2 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Chester, NY hotels
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

12 Cheap hotels in Chester, NY

Best Chester, NY hotels for families

Holiday Inn Express And Suites Montgomery By Ihg - Chester, NY
9.0 2386 reviews
Chester, NY
22/06 – 22/07
A$288/nighttotal: A$8640 (30 )

Holiday Inn Express And Suites Montgomery By Ihg

1 2
hotel , Montgomery
The Holiday Inn Express And Suites Montgomery, An Ihg Hotel is located in Montgomery, just 54 miles from LaGuardia Airport. This 2-star hotel is rated "very good" by previous guests for its cleanliness, location, and overall experience.
The hotel offers comfortable accommodation with a TV, air conditioning, a seating area, and a private bathroom with free toiletries. Guests can enjoy amenities such as an indoor pool, fitness centre, free Wi-Fi, and on-site parking.
The Orange Inn Boutique Hotel - Chester, NY
9.8 182 reviews
Chester, NY
24/07 – 26/07
A$604/nighttotal: A$1208 (2 )

The Orange Inn Boutique Hotel

1 2
hotel , Goshen
The Orange Inn Boutique Hotel is located in Goshen, just a short walk from the Orange County Genealogical Society and a short drive from LEGOLAND® New York. This 2-star hotel has received excellent user ratings.
The accommodation offers a range of amenities, including a restaurant, bar, and terrace. Guests can also enjoy free parking, air conditioning, and a fireplace in the lobby.

Best Chester, NY hotels with a pool

Among the 3 accommodations in Chester, NY, here are the 3 best hotels with a pool

Days Inn By Wyndham Middletown - Chester, NY
Chester, NY
19/06 – 21/06
A$272/nighttotal: A$544 (2 )

Days Inn By Wyndham Middletown

1 3
hotel , Middletown
The Days Inn By Wyndham Middletown is situated in the centre of Middletown, within easy walking distance of the town square and just a short drive from the Middletown Museum. This 2-star hotel provides a comfortable and convenient base for exploring the area.
The hotel features a range of facilities for guests including an indoor and outdoor pool, a restaurant, and room service. Guests can also enjoy a variety of amenities such as Wi-Fi, parking, a safe, and a newspaper stand.
Holiday Inn Express Hotel & Suites Chester By Ihg - Chester, NY
8.5 1632 reviews
Chester, NY
22/06 – 22/07
A$325/nighttotal: A$9750 (30 )

Holiday Inn Express Hotel & Suites Chester By Ihg

1 2
hotel , Chester
The Holiday Inn Express Hotel & Suites Chester, An Ihg Hotel is located just a short drive from Goose Pond Mountain State Park and around 7 miles from Goshen, New York, offering a convenient base for exploring the area. It is a 2-star hotel that has received very good user ratings for its location, cleanliness, and overall experience.
The hotel offers a range of facilities for guests, including a swimming pool, Jacuzzi, fitness centre, and restaurant. It also provides comfortable rooms with modern amenities, such as free Wi-Fi and a complimentary breakfast.
La Quinta Inn & Suites By Wyndham Middletown-goshen - Chester, NY
9.4 1106 reviews
Chester, NY
19/06 – 21/06
A$568/nighttotal: A$1136 (2 )

La Quinta Inn & Suites By Wyndham Middletown-goshen

1 3
hotel , Scotchtown
La Quinta Inn & Suites by Wyndham Middletown is located in Scotchtown, just a short walk from the Middletown Train Station and within a mile of Silver Lake and the Galleria at Crystal Run Mall. This 2-star hotel is a popular choice for travellers, with excellent user ratings for its cleanliness and location.
The hotel offers a range of amenities to make your stay comfortable, including an indoor heated pool and jacuzzi, an outdoor patio, and a fitness centre. Guests can also enjoy a restaurant on-site, a 24-hour shop, and free Wi-Fi in all rooms.

Frequently asked questions about hotels in Chester, NY

  • How can travelers relax during a week in and arond Chester, NY?

    Chester is perfect for a relaxing getaway. You can unwind with a scenic hike in Sterling Forest State Park, enjoy a leisurely bike ride along the scenic Hudson River Valley Rail Trail, or simply relax by the river at one of the many parks.
  • What are the best hotels with a swimming pool in Chester, NY?

  • What amenities can travelers expect in hotel rooms in Chester, NY?

    Most hotels in Chester offer basic amenities like comfortable beds, private bathrooms, and free Wi-Fi. Some may also have additional features like swimming pools, fitness centres, or breakfast included.
  • What are the most popular 2, 3 and 4-star hotels in Chester, NY?

    Among 2, 3 and 4-star hotels in Chester, NY, Fairfield Inn & Suites Goshen Middletown, Holiday Inn Express Hotel & Suites Chester By Ihg and The Orange Inn Boutique Hotel are the most popular ones.

  • When is the best time to book a hotel in Chester, NY?

    The best time to book a hotel in Chester is during the shoulder seasons, spring and autumn, when the weather is pleasant and the crowds are smaller. You might find better deals during these periods.
  • What are the best luxury hotels in Chester, NY?

    Orange Inn Boutique Hotel is among the best luxury hotels in Chester, NY.

  • What are some pet-friendly activities in and around Chester, NY?

    You can enjoy a walk with your furry friend along the Hudson River Walkway, visit the pet-friendly Chester Village Green, or take a scenic drive through the nearby Sterling Forest State Park. Many restaurants in the area also have outdoor seating that welcomes pets.
  • What are the best family friendly hotels in Chester, NY?

  • Which towns or cities worth a visit near Chester, NY?

    You can easily visit nearby towns like Warwick, Goshen, and Newburgh. Each town has its unique charm and offers a variety of attractions, restaurants, and shops to explore.
  • What are the best hotels with jacuzzi in Chester, NY?

    Holiday Inn Express Hotel & Suites Chester By Ihg is the best hotel with a jacuzzi in Chester, NY.

Destinations nearby

Best Chester, NY hotels with breakfast

Among the 2 accommodations in Chester, NY, here are the 2 best hotels with breakfast

Homewood Suites By Hilton Newburgh-stewart Airport - Chester, NY
9.2 1638 reviews
Chester, NY
22/06 – 22/07
A$605/nighttotal: A$18150 (30 )

Homewood Suites By Hilton Newburgh-stewart Airport

1 2
hotel , Orange Lake
The Homewood Suites By Hilton Newburgh-stewart Airport is located in New Windsor, just a short drive from Orange Lake, making it a convenient option for those exploring the area. This 3-star hotel has consistently received excellent user reviews for its cleanliness and overall experience.
The hotel offers spacious suites with separate living and sleeping areas, perfect for families or groups. Guests can enjoy a range of amenities including an indoor pool, fitness centre, complimentary breakfast, and a business centre.
Stagecoach Inn - Chester, NY
9.5 128 reviews
Chester, NY
24/07 – 26/07
A$715/nighttotal: A$1430 (2 )

Stagecoach Inn

1 2
hotel , Goshen
The Stagecoach Inn is located in Goshen, just a short drive from the Metro-North Harriman Station, Bear Mountain State Park, and the DM Weil Gallery. This 5-star hotel has consistently received excellent user ratings for its service, cleanliness, and location.
The Stagecoach Inn offers comfortable and well-appointed rooms with a range of amenities, including a restaurant, bar, and free parking. Guests can enjoy a continental breakfast, relax on the terrace, or explore the surrounding area, which offers beautiful natural scenery and cultural attractions.

Best Chester, NY hotels with parking

La Quinta Inn & Suites By Wyndham Middletown-goshen - Chester, NY
8.9 569 reviews
Chester, NY
19/06 – 21/06
A$491/nighttotal: A$982 (2 )

La Quinta Inn & Suites By Wyndham Middletown-goshen

1 3
hotel , Scotchtown
La Quinta Inn & Suites by Wyndham Middletown is located just 1.6 kilometres from Silver Lake and a 13-minute walk from Middletown Train Station, making it a convenient base for exploring the area. The 2-star hotel has received very good user ratings for its cleanliness and location.
The hotel offers a range of amenities, including a swimming pool, jacuzzi, and fitness centre, as well as a meeting room for business travellers. Guests can also enjoy a traditional decor in their rooms, with free Wi-Fi and a work desk.
Fairfield Inn & Suites Goshen Middletown - Chester, NY
8.8 1990 reviews
Chester, NY
19/06 – 21/06
A$568/nighttotal: A$1136 (2 )

Fairfield Inn & Suites Goshen Middletown

1 3
hotel , Goshen
The Fairfield Inn & Suites Goshen Middletown is conveniently located near Route 17, just a short drive from both Good Time Park and the town of Middletown. This 3-star hotel has received very good user ratings, making it a popular choice for travellers.
The hotel offers comfortable rooms with modern amenities. Guests can enjoy a range of facilities including a swimming pool, fitness centre, restaurant, and bar, as well as a complimentary continental breakfast.
La Quinta Inn & Suites By Wyndham Middletown-goshen - Chester, NY
9.4 1106 reviews
Chester, NY
19/06 – 21/06
A$568/nighttotal: A$1136 (2 )

La Quinta Inn & Suites By Wyndham Middletown-goshen

1 3
hotel , Scotchtown
La Quinta Inn & Suites by Wyndham Middletown is located in Scotchtown, just a short walk from the Middletown Train Station and within a mile of Silver Lake and the Galleria at Crystal Run Mall. This 2-star hotel is a popular choice for travellers, with excellent user ratings for its cleanliness and location.
The hotel offers a range of amenities to make your stay comfortable, including an indoor heated pool and jacuzzi, an outdoor patio, and a fitness centre. Guests can also enjoy a restaurant on-site, a 24-hour shop, and free Wi-Fi in all rooms.
Hampton Inn Harriman Woodbury - Chester, NY
8.9 3801 reviews
Chester, NY
19/06 – 21/06
A$589/nighttotal: A$1178 (2 )

Hampton Inn Harriman Woodbury

1 3
hotel , Woodbury
The Hampton Inn Harriman Woodbury is located just off Route 87 and Route 6, a short drive from Harriman State Park and Falkirk Estate and Country Club. This 3-star hotel is popular with visitors, receiving a "very good" user rating.
The hotel offers a range of modern rooms with comfortable features like LCD TVs, microwaves, and refrigerators. Guests can enjoy the indoor swimming pool, hot tub, fitness centre, and a daily hot buffet breakfast.
©2026 cozycozy.com