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Our top choices for Chester hotels

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, (1,001 reviews)
"great stay"
United States
Annette
The price is NZ$266
includes taxes & fees
26 July - 27 July
Holiday Inn Express Hotel & Suites Chester by IHG

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (235 reviews)
"I had a perfect stay with my girlfriend for a long weekend. Eric and Susie were amazing hosts, serving delicious breakfast each day. The hot tub was luxurious and the area was beautiful. I’d 100% come back."
United States
Anna
The price is NZ$431
includes taxes & fees
30 June - 1 July
The Dominion House Bed & Breakfast

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very good, (62 reviews)
"Family trip with 3 kids and we love it"
Canada
Pheng Theam
The price is NZ$240
includes taxes & fees
28 July - 29 July
Comfort Suites Central Valley - Woodbury

Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (123 reviews)
"Very nice accommodations & staff."
United States
Laurie
The price is NZ$209
includes taxes & fees
29 June - 30 June
Tin Brook Bed & Breakfast

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (630 reviews)
"Very clean and staff helpful "
United States
Kaiden
The price is NZ$220
includes taxes & fees
29 June - 30 June
Days Inn by Wyndham Wurtsboro

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1,005 reviews)
"Gorgeous setting, beautiful and comfortable room and easy access."
United States
Gwen
The price is NZ$301
includes taxes & fees
30 June - 1 July
Overlook Lodge at Bear Mountain

High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (156 reviews)
"Great place if looking for pet friendly quiet stat"
United States
John H
The price is NZ$174
includes taxes & fees
30 June - 1 July
High Point Motel

Rolling Hills Motel

Rolling Hills Motel
2.0 star property
Sussex
8.6 out of 10, Excellent, (216 reviews)
"Great staff and clean."
United States
John
The price is NZ$171
includes taxes & fees
29 June - 30 June
Rolling Hills Motel

The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (168 reviews)
"The location was very convenient"
United States
Stephen
The price is NZ$171
includes taxes & fees
30 June - 1 July
The Hamlet Inn at Warwick

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, (877 reviews)
"Our stay for a day was great."
United States
Chime
The price is NZ$201
includes taxes & fees
26 July - 27 July
Holiday Inn Express & Suites Montgomery by IHG

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (169 reviews)
"Did you ever want to experience what it would be like to stay at a bed in breakfast? Well this is the place to go! So quaint and cute! Located right in the heart of the town of Montgomery. Plenty of things to walk to and see in the area. Brianna the manager was wonderful. Very helpful and informative. The breakfast choices were delicious. Would definitely stay here again and recommend it to others."
United States
roxanne
The price is NZ$225
includes taxes & fees
29 June - 30 June
Borland House Inn

Appalachian Motel

Appalachian Motel
2.0 star property
Vernon
7.6 out of 10, Good, (541 reviews)
"The rooms are very basic, but we had everything we needed for our stay. A really nice surprise was how comfortable the beds were. The motel is close to hiking trails. The parking lot for hiking Stairway to Heaven was a 2 minute drive from the motel. If you stay here in the winter, it is only a 5 minute drive from Mountain Creek ski resort. We would stay here again."
United States
Lorrie
The price is NZ$137
includes taxes & fees
29 June - 30 June
Appalachian Motel

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,101 reviews)
"The room was pristine, breakfast great, ample and easy parking, very warm staff!"
United States
Akunna
The price is NZ$225
includes taxes & fees
19 July - 20 July
Sleep Inn & Suites Monroe - Woodbury

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,002 reviews)
"Breakfast menu was poor at best."
United States
Constance
The price is NZ$208
includes taxes & fees
26 July - 27 July
Quality Inn near Mountain Creek

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,000 reviews)
"I spoiled myself and had a room with a little balcony that overlooked very well landscaped garden/outdoor seating areas. This was definitely an escape from home restful stay!"
United States
Diane
The price is NZ$247
includes taxes & fees
20 July - 21 July
Courtyard by Marriott Middletown Goshen

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,005 reviews)
"Nice Clean Hotel"
United States
James
The price is NZ$238
includes taxes & fees
19 July - 20 July
Hampton Inn by Hilton Middletown

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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very good, (1,003 reviews)
"We stopped here for the night and it was perfect. Clean room and courteous staff."
United States
Kathleen
The price is NZ$205
includes taxes & fees
12 July - 13 July
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook
2.5 star property
Montgomery
6.4 out of 10, (1,002 reviews)
"Simple and easy quiet stay for overnight"
United States
Jose
The price is NZ$152
includes taxes & fees
29 June - 30 June
Super 8 by Wyndham Montgomery Maybrook

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.2 out of 10, Very good, (146 reviews)
"Great affordable stay overall."
United States
Caroline
The price is NZ$190
includes taxes & fees
12 July - 13 July
Spark by Hilton Fishkill

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (717 reviews)
"Stayed here numerous times friendly staff and very nice place close to post."
United States
Michael
The price is NZ$262
includes taxes & fees
12 July - 13 July
West Point Motel
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Stay near popular Chester attractions

Learn more about Chester

Lace up your hiking boots and hit the trails at Goosepond Mountain State Park for stunning views. After working up an appetite, head to Castle Fun Centre for go-karts, mini-golf, and arcade games.

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

Top Chester Hotel Reviews

Recent Reviews in Chester

More cheap accommodation in Chester

Find out more about Chester

Top reasons to visit Chester

  • Charming City Centre: Chester boasts a welcoming city centre filled with friendly locals, perfect for leisurely strolls and shopping.
  • Family-Friendly Activities: Enjoy a mix of entertainment options, including a delightful cinema and a leisure centre catering to all ages.
  • Stunning Outdoor Adventures: Explore the beautiful Cheshire countryside, national parks, and lakes for unforgettable outdoor experiences.
  • Diverse Accommodation: Choose from a range of lodging options, from agritourism to modern hotels, catering to various needs.
  • Rich Cultural Experiences: Visit local attractions like Chester Zoo and Chester Cathedral for a taste of the area's heritage.

Find great hotels near Chester

Discover a variety of accommodation options in Chester, New York, where you can enjoy a perfect blend of comfort and convenience. Whether you’re seeking a family-friendly getaway, a pet-friendly stay, or a space tailored for business travel, Chester's hotels cater to all types of visitors. With options ranging from charming agritourism properties to modern hotels, you're sure to find the ideal base for your adventure in this picturesque region.

  • Red Roof Inn & Suites Newburgh – Stewart Airport/West Point: Located 20.9km from Chester, Red Roof Inn & Suites Newburgh – Stewart Airport/West Point offers a budget-friendly accommodation that caters to families, business travellers, and those with pets. Guests appreciate the welcoming atmosphere and the convenience of free cribs for children. The hotel embraces a pet-friendly policy, accommodating your furry companions with various restrictions. With a guest rating of 8.4 out of 10, this property ensures a comfortable stay while providing essential amenities that cater to both business and leisure needs.
  • Super 8 by Wyndham Middletown: Just 14.5km from Chester, Super 8 by Wyndham Middletown is a budget motel that delivers a straightforward and comfortable lodging experience. Guests can unwind with entertainment options including television, satellite TV, and premium channels. The nearby outlet shopping adds a touch of excitement for those looking to explore the local scene. This property is an excellent choice for budget-conscious travellers seeking a convenient base from which to experience the surrounding area.
  • Howard Johnson by Wyndham Newburgh/West Point: Situated 22.5km from Chester, Howard Johnson by Wyndham Newburgh/West Point provides a budget-friendly option tailored for business travellers. With a focus on practicality and comfort, this hotel features essential amenities designed to meet the needs of those on work-related trips. The property offers a convenient location, making it easy for guests to access key business areas and attractions in the vicinity.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly experiences and vibrant city life. Explore the charming Chester city centre, where friendly locals create a welcoming atmosphere. Venture into the stunning Cheshire countryside for outdoor adventures, and indulge in a varied shopping experience that caters to all budgets. Whether you're seeking a relaxing getaway or a lively family vacation, Chester promises a memorable stay filled with warmth and hospitality.

  • Middletown: Situated a mere 16.1km from Chester, Middletown is a vibrant city perfect for family adventures and entertainment. With a diverse range of attractions, visitors can enjoy the lively shopping mall centre and various resorts. The city is particularly bustling during the peak months of April and June to July, making it an excellent time to explore local landmarks such as the theme park and tourist precinct. Whether you're looking for a fun day out or a shopping spree, Middletown offers a rich urban experience amidst its charming surroundings.
  • Goshen: Just 6.4km from Chester, Goshen is a delightful city that appeals to families and entertainment seekers alike. Known for its welcoming atmosphere, the city draws visitors throughout the year, with peak times in March, July, and September. Goshen features a variety of popular activities, including visits to its shopping mall centre and local resorts. The nearby theme park and tourist precinct offer exciting escapades for all ages, ensuring that your time in Goshen is filled with memorable experiences.
  • Monroe: Only 8.0km from Chester, Monroe is a charming city that balances family fun with business opportunities. The city experiences a steady stream of visitors, peaking in June to July and September. Monroe boasts a mix of shopping centres and ski venues, making it a great destination for both leisure and business travellers. Nature lovers will appreciate the proximity to stunning landmarks such as the lake and mountain, providing a perfect backdrop for outdoor activities. Monroe's unique offerings make it an ideal spot for exploring the great outdoors while enjoying city conveniences.

Things to do near Chester

Shopping

Chester offers a charming shopping experience with local boutiques and gift shops. For a wider selection, if you're up for a drive, head to nearby shopping malls like Woodbury Common Premium Outlets, about 24.1km away, where you can find an array of designer brands at discounted prices.

Recreation

In Chester, the Mohonk Mountain House offers a serene spa experience with treatments inspired by nature, surrounded by breathtaking mountain views. Nearby, the Hudson Valley offers hiking trails and peaceful lakes, perfect for leisurely strolls and reconnecting with nature's beauty.

Adventure

Experience thrilling motor racing at Orange County Fair Speedway, located 14.5km from Chester, where the adrenaline rush of the track awaits. For a different adventure, head to Zoom Ziplines, 27.4km away, and soar through the trees, enjoying the outdoor scenery. Palisades Climb Adventure, 40.2km from Chester, offers a fun-filled ropes course and zipline experience.

Nightlife

Explore the lively atmosphere at The Chester Tavern, where you can enjoy a variety of beers and local bands. For a more laid-back vibe, visit The Copper Door for tasty cocktails and a welcoming ambience. Both spots offer a taste of Chester's vibrant nightlife scene.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chester

Chester, New York, is perfect for family and entertainment-themed getaways, offering a variety of attractions like national parks, lakes, and urban parks. Visitors can enjoy outdoor activities, cultural experiences, and stunning scenery. While exploring the area, consider staying at local hotels and visiting attractions such as Chester Zoo, Chester Racecourse, and Chester Cathedral for a memorable experience.

  • Bear Mountain State Park: Located 24.1km from Chester, this expansive park offers stunning landscapes and a variety of outdoor activities. Enjoy scenic hikes, wildlife spotting, and breathtaking views from the summit, making it ideal for adventure seekers and nature lovers alike.
  • Algonquin Park: Just 25.7km away, this urban park blends city life with natural beauty. Families can enjoy spacious picnic areas, walking paths, and playgrounds, providing a perfect escape from the hustle and bustle of urban living.
  • Arrow Park Lake and Lodge: Situated 11.3km from Chester, this picturesque lake features a charming beach and scenic surroundings. It's a romantic spot for couples looking to relax, swim, or enjoy a peaceful day by the water.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January28.0°F (-2.2°C)Light RainMostly SunnyAverageSlightly Low
February29.8°F (-1.2°C)Light RainMostly SunnySlightly LowSlightly Low
March37.4°F (3.0°C)Light RainMostly SunnyAverageSlightly Low
April48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
May59.4°F (15.2°C)Light RainMostly SunnyAverageAverage
June67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
July73.9°F (23.3°C)Light RainMostly SunnySlightly HighAverage
August72.0°F (22.2°C)Light RainMostly SunnyAverageSlightly High
September64.9°F (18.3°C)Light RainMostly SunnySlightly HighSlightly High
October54.0°F (12.2°C)Light RainMostly SunnyAverageSlightly High
November42.1°F (5.6°C)Light RainMostly SunnySlightly LowAverage
December34.2°F (1.2°C)Light RainMostly SunnySlightly LowAverage

The nearest major airports for your trip to Chester

Flying into Chester, New York, is convenient with three major airports nearby. John F. Kennedy International Airport (JFK) is 90.1km away, with excellent hotels like The William Vale and Arlo Williamsburg, both 17.7km from the airport. Newark Liberty International Airport (EWR) is 75.6km away, offering luxury options such as The Dominick and Four Seasons Hotel New York Downtown, situated 14.5km from the airport. LaGuardia Airport (LGA) is 74.0km from Chester, featuring top-rated hotels like Hilton Club The Quin New York and The Plaza, both approximately 5 to 9.7km from the airport. Each airport provides accessible transportation to these accommodations, ensuring a pleasant arrival experience.

Frequently asked questions

What is the best area to stay in Chester?
The best area to stay in Chester is the village centre, particularly around Main Street and the surrounding blocks.

This area is the heart of Chester, offering a pleasant and convenient experience for visitors. Main Street is lined with local shops, eateries, and historic buildings, creating a welcoming feel. You'll find attractions like the Chester Historical Society Museum and the Sugar Loaf Performing Arts Center nearby. The village is also known for its strong community spirit and regular events.

Couples looking for a relaxing getaway will appreciate the village centre. It offers a selection of cosy bed and breakfasts and boutique hotels, providing a more personal touch. You can enjoy strolls through the village, browse antique shops, and dine at local restaurants without needing to drive. The nearby Black Dirt Region is also easily accessible for wine tasting or farm visits, making for enjoyable day trips.

For families, staying within the village centre provides easy access to the local parks and ice cream parlours. The village green often hosts community gatherings and is a pleasant spot for children to play.
What are the best hotels in Chester that travellers recommend?
For hotels in Chester that travellers recommend, the Holiday Inn Express Hotel & Suites Chester by IHG is a superb choice.

This hotel, with an 8.6 rating, offers comfortable and clean rooms with premium bedding, ensuring a restful stay. Guests frequently praise the friendly and great staff, as well as the delicious and good complimentary breakfast, including convenient to-go options. The indoor pool is known for being clean, and there are pool sun loungers available for relaxation. The hotel is also located within a shopping district and is just 0.6 km from Castle Fun Centre and 3.2 km from LEGOLANDĀ® New York.
What are the best family hotels in Chester?
For families visiting Chester, the Holiday Inn Express Hotel & Suites Chester by IHG and The Dominion House Bed & Breakfast are both excellent choices.

The Holiday Inn Express Hotel & Suites Chester by IHG, with a rating of 8.6, is a highly recommended option for families. Guests frequently mention the friendly staff and delicious complimentary breakfast. The hotel offers comfortable and clean rooms, some with sofa beds and connecting room options, which are ideal for families. A clean pool is also available for guests to enjoy. It is conveniently located just 0.6 km from the Castle Fun Centre and 3.2 km from LEGOLANDĀ® New York. Free self-parking and free WiFi are also provided.

Another superb choice is The Dominion House Bed & Breakfast, which boasts an outstanding rating of 9.6. This accommodation provides amenities such as cribs and a shared children's playground, suiting families. Guests can also benefit from free breakfast, free self-parking, and free wired internet in public areas.
What hotels in Chester offer free breakfast?
Two excellent hotels in Chester offering complimentary breakfast are The Dominion House Bed & Breakfast and the Holiday Inn Express Hotel & Suites Chester by IHG.

The Dominion House Bed & Breakfast, with an impressive 9.6 rating, provides a delightful free breakfast to start your day. Guests also benefit from complimentary wired internet in public areas, free RV, bus, and truck parking, and free toiletries.

Another great option is the Holiday Inn Express Hotel & Suites Chester by IHG, a 3-star hotel with an 8.6 rating. This hotel offers a free breakfast, including a convenient to-go option, along with free self-parking and complimentary wired internet in public areas. Guests frequently praise the friendly staff, delicious breakfast, and comfortable, clean rooms.
What are the best budget hotels in Chester?
For budget hotels in Chester, consider the Holiday Inn Express Hotel & Suites Chester by IHG or The Dominion House Bed & Breakfast.

The Holiday Inn Express Hotel & Suites Chester by IHG, with an 8.6 rating, offers comfortable and clean rooms, and guests frequently highlight the friendly and great staff. The hotel provides free Wi-Fi, free wired internet in public areas, and complimentary toiletries. A delicious and good breakfast is included, and a to-go breakfast option is also available. Free self-parking is another convenient feature.

Another excellent option is The Dominion House Bed & Breakfast, which boasts an impressive 9.6 rating. This charming bed and breakfast provides free wired internet in public areas, free toiletries, and complimentary breakfast. Guests will also appreciate the free self-parking and the availability of free RV, bus, and truck parking.
What are the best hotels in Chester near LEGOLANDĀ® New York?
For a highly-rated hotel in Chester near LEGOLANDĀ® New York, the Holiday Inn Express Hotel & Suites Chester by IHG is an excellent option.

This hotel, with an 8.6 rating, is conveniently located just 3.2 kilometres from LEGOLANDĀ® New York. Guests frequently praise the friendly and great staff, delicious and good breakfast, and comfortable and clean rooms. It has features friendly for families such as connecting rooms and sofa beds, as well as complimentary breakfast with a to-go option, free self-parking, and free Wi-Fi. The clean pool is also a popular feature.
When is the best time to go to Chester?
The best time to visit Chester, New York, is generally during the late spring (May to June) and early autumn (September to October) when the weather is pleasant for outdoor activities and exploring the region.

Late spring offers comfortable temperatures, typically ranging from 15°C to 25°C, making it ideal for walking, visiting local farms, and enjoying the natural beauty of the Hudson Valley. The foliage is lush and green, and many local attractions, such as farmers' markets and outdoor events, begin to open for the season. This period is particularly good for solo travellers or couples looking for a relaxed getaway with opportunities for scenic drives and light outdoor recreation without the peak summer crowds.

Early autumn provides a spectacular display of fall colours, especially from late September through October, with temperatures usually between 10°C and 20°C. This is a prime time for couples or solo travellers who appreciate picturesque landscapes and outdoor activities like apple picking at local orchards or exploring nearby state parks. The crisp air and vibrant scenery make it a popular time for wine tasting tours at local vineyards.

While summer (July to August) is also a popular time with warmer weather for lakes and outdoor adventures, it can be busier and hotter.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to 'My Trips' and selecting your reservation. To find flexible deals, filter your search by 'Fully refundable property' for hotels in Chester.
How can I save on a hotel booking in Chester with Expedia?
One Keyā„¢ – Expedia's free travel rewards programme – gives you instant access to perks and Member Prices on Chester hotels. Plus, you'll earn OneKeyCashā„¢* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Chester?
Prices for hotels in Chester often vary, but you can find a great deal from NZ$123 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by 'Price: low to high' for our cheapest rates.

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