Photo by Elizabeth Massa Peroulakis

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Top hotels and accommodation in Chester

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1012)
"Great Indian restaurant in the hotel!"
United States
Chris
The price is AU$182
includes taxes & fees
3 Nov - 4 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (772)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is AU$150
includes taxes & fees
5 Nov - 6 Nov
Berkshires Untold
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1016)
"Good breakfast King rooms are the best facing the mountains Recently remodeled "
United States
Susan M
The price is AU$218
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very good, (915)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is AU$177
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AU$279
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
River Valley Inn
2.0 star property
8.6 out of 10, Excellent, (82)
"Great quiet motel. "
United States
Hector
The price is AU$204
includes taxes & fees
16 Nov - 17 Nov
River Valley Inn
Red Roof Inn PLUS+ West Springfield
2.5 star property
7.0 out of 10, Good, (1020)
"The staff was very helpful and nice"
United States
Cristal
The price is AU$172
includes taxes & fees
2 Nov - 3 Nov
Red Roof Inn PLUS+ West Springfield
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (55)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
United States
Marti
The price is AU$246
includes taxes & fees
3 Nov - 4 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (784)
"Nice hotel. Very friendly and professional staff. "
United States
Magen
The price is AU$181
includes taxes & fees
11 Nov - 12 Nov
Hotel On North
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (554)
"Excellent location, friendly service, clean, comfortable room."
United States
Beth
The price is AU$129
includes taxes & fees
22 Oct - 23 Oct
Travelodge by Wyndham Great Barrington Berkshires
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1016)
"Picture perfect Inn"
United States
jeff
The price is AU$311
includes taxes & fees
9 Nov - 10 Nov
The Red Lion Inn
Candlewood Suites West Springfield by IHG
2.5 star property
8.4 out of 10, Very good, (772)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is AU$172
includes taxes & fees
13 Nov - 14 Nov
Candlewood Suites West Springfield by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0 out of 10, Wonderful, (763)
"Lovely spot, great accommodations, friendly staff, and great location."
United States
Joanne
The price is AU$220
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (678)
"This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. "
United States
Tina
The price is AU$175
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (722)
"Great stay, perfect "
United States
Lawrence
The price is AU$194
includes taxes & fees
3 Nov - 4 Nov
Berkshire Mountain Lodge
La Quinta Inn & Suites by Wyndham Springfield MA
3.0 star property
8.2 out of 10, Very good, (1307)
"Love this hotel, 2nd time staying here, family friendly, clean, nice room, great restaurants, convenient location"
United States
Lynne
The price is AU$200
includes taxes & fees
9 Nov - 10 Nov
La Quinta Inn & Suites by Wyndham Springfield MA
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very good, (554)
"Very quiet and comfortable "
United States
Beth
The price is AU$204
includes taxes & fees
18 Nov - 19 Nov
The Constance by the Lenox Collection
Quality Inn West Springfield
2.5 star property
7.0 out of 10, Good, (1023)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
United States
Danielle
The price is AU$158
includes taxes & fees
16 Nov - 17 Nov
Quality Inn West Springfield
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (640)
"Stayed one night just because we had been driving for 10 hours but nice place for the price. "
United States
patricia
The price is AU$98
includes taxes & fees
10 Nov - 11 Nov
Econo Lodge Lee - Great Barrington
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (745)
"The property is very nice and the staff was extremely friendly and helpful."
United States
Greg
The price is AU$245
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.
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Stay near popular Chester attractions

Learn more about Chester

Experience the hiking, camping and theatre in Chester!

Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

More cheap accommodation in Chester

Find out more about Chester

Top reasons to visit Chester

  • Stunning Scenery: Chester boasts breathtaking landscapes, perfect for outdoor enthusiasts and romantic getaways.
  • Vibrant Cultural Scene: Enjoy theatre performances, music concerts, and local art, enriching your experience.
  • Outdoor Adventures: Explore urban parks, nature reserves, and recreational activities for all ages.
  • Historic Attractions: Visit Chester Zoo, historic sites, and the iconic Chester Cathedral.
  • Charming Accommodation: Relax in cosy bed and breakfasts or well-equipped hotels catering to all travellers.

Find great hotels near Chester

Discover a range of charming accommodation options in Chester, Massachusetts, perfect for your next getaway. From cosy bed and breakfasts to well-equipped hotels, you'll find a variety of choices that cater to adventure seekers, families, and pet owners alike. Whether you're searching for top Chester hotels or a quaint place to unwind, Chester offers delightful lodging to enhance your holiday experience.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the picturesque Berkshires, this 3.5-star resort offers a vibrant adventure-focused experience for guests. Perfect for those seeking an LGBTQIA-friendly environment, the resort provides easy access to skiing and adventure sports. With amenities such as onsite recreation, ski shuttles, and nearby hiking and biking trails, outdoor enthusiasts will find plenty to explore. The welcoming atmosphere and variety of activities make it an excellent choice for adventure-seeking travellers looking to create unforgettable memories.
  • The Black Swan Lee - Lenox, Ascend Hotel Collection: This charming 3-star hotel is designed for families and pet lovers alike, offering a delightful blend of adventure and comfort. Located in a scenic area, guests can enjoy kayaking, fishing, and skiing, all within close proximity. The hotel prides itself on its family-friendly amenities, including cribs and safety features for children, ensuring peace of mind for parents. With a pet-friendly policy that allows dogs, The Black Swan is an inviting choice for those looking to enjoy a memorable family getaway with their furry companions.
  • Quality Inn Westfield - Springfield: Ideal for families and business travellers, this Quality Inn offers a practical yet comfortable stay only a short drive from Chester. With a focus on convenience, the hotel features a business centre and child-friendly amenities, making it suitable for both work and leisure. The pet-friendly policy welcomes furry guests, ensuring everyone is accommodated. Guests appreciate the warm service and accessible location, perfect for those looking to balance family time and business needs during their stay.

Where to stay near Chester

Chester, Massachusetts, offers a delightful blend of outdoor adventures and romantic scenery, perfect for families and couples alike. Explore the charming Chester city and its picturesque countryside, where you can enjoy leisurely strolls and recreational activities. Nearby attractions provide a relaxing atmosphere, ideal for shopping and unwinding. Whether you’re seeking vibrant city life or tranquil nature, Chester and its surroundings promise an unforgettable vacation experience.

  • Lenox: Situated 27.4km from Chester, Lenox is a charming city that attracts visitors year-round, particularly from June to August. Known for its vibrant entertainment scene, it’s a great spot for romantic getaways and family fun. Enjoy live music concerts, theatrical performances, and winter skiing at nearby resorts. Nature lovers will appreciate the stunning lakes and mountains that surround the area, making it ideal for outdoor activities. Don’t miss the local event conference venue, which often hosts exciting events and gatherings.
  • The Berkshires: Just 19.3km away from Chester, The Berkshires is a picturesque region that offers a blend of adventure and stunning scenery, attracting visitors throughout the year. Peak travel occurs from June to August, with outdoor enthusiasts flocking to its ski fields and resorts during winter. Hiking, skiing, and exploring the breathtaking landscapes are popular activities here. The area's lakes and mountains provide ample opportunities for relaxation and exploration, making it a must-visit destination for nature lovers.
  • Sherwood Forest: A mere 8.0km from Chester, Sherwood Forest is a delightful neighbourhood that boasts a mix of romantic escapes and outdoor experiences. Visitors are drawn here from July to August and in October, enjoying recreational areas and local theatres. The scenic beauty, featuring lakes and a racetrack, adds to its charm. Whether you’re looking to dance the night away or simply enjoy a peaceful stroll, Sherwood Forest is the perfect spot to unwind and connect with nature.

Things to do near Chester

Chester, Massachusetts, is perfect for outdoor and romantic getaways, boasting stunning scenery. Visitors can enjoy a variety of activities including theatre performances, music concerts, and educational experiences. For golf enthusiasts, there are notable golf courses to explore. This charming town provides a delightful blend of nature and culture, making it an ideal destination for a relaxing vacation.

Shopping

In Chester, you can shop at the Berkshire Mountain Country Store, just 22.5km away, offering unique gifts and local products. If you're up for a drive, visit the Lee Premium Outlets 20.9km away for great deals on brand-name items, or Guido's Marketplace, located 27.4km away, for a vibrant market experience.

Recreation

Jacob's Pillow, a renowned dance venue 11.3km from Chester, offers a vibrant mix of romance and culture. For relaxation, visit Goose Pond Reservation, located 17.7km away, where you can unwind amidst tranquil surroundings. Lastly, enjoy outdoor sports at Wyndhurst Golf & Club, situated 24.1km from Chester.

Adventure

Otis Ridge, located 14.5km from Chester, offers thrilling skiing experiences with a vibrant sports atmosphere. For hiking enthusiasts, the Skyline Trail, 11.3km away, provides stunning outdoor scenery and adventure. Additionally, Blandford Ski Area, also 11.3km from Chester, promises more exciting skiing opportunities.

Nightlife

In Chester, Shakespeare and Company offers a vibrant theatre atmosphere with a blend of culture and romance, located 25.7km away. For family fun, Spare Time Bowling’s arcadeAdventureZone, 29.0km from Chester, promises adventure, while the Academy of Music Theatre, also 29.0km away, showcases captivating performances.

Booking tips and Expedia advantages for Chester

To save money on your trip to Chester, consider visiting in March or between December and January, as these months offer lower accommodation prices. Tuesdays are the cheapest days to stay, while Saturdays are the most expensive. Use Expedia to find great deals by sorting prices from lowest to highest, and look for package deals that combine flights, activities, and hotel stays for added savings. Don’t forget to explore free activities in Chester to make the most of your budget!

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are March and December to January, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chester is Tuesday. The most expensive day to stay in Chester is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you’re after. To find the most affordable prices and offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some dollars by combining your Chester hotel stay with your flights and activities through an Expedia package deal.

Find the best attractions in and around Chester

Chester, Massachusetts, is perfect for an outdoor, romantic getaway with stunning scenery. Visitors can explore urban parks, nature reserves, and historic houses, catering to families and adventure seekers alike. Key attractions include Chester Zoo, the historic sites of Chester, and Chester Cathedral. For a comfortable stay, consider the best hotels in Chester, and don't miss the excitement of Chester Racecourse. Enjoy a delightful blend of nature and history in this charming town!

  • National Shrine of the Divine Mercy: Located 27.4km from Chester, this serene shrine offers a peaceful retreat infused with spiritual culture. Visitors can experience the tranquil gardens and stunning architecture, making it a perfect spot for reflection and prayer.
  • The Mount: Situated 25.7km away, this historic house was once the home of renowned author Edith Wharton. The Mount features beautifully landscaped gardens and elegant architecture, offering a glimpse into the literary past while immersing visitors in rich cultural vibes.
  • Chester Town Hall: Nestled in the heart of Chester, this historic civic government building showcases charming local architecture and serves as a hub for community events, embodying the town’s cultural heritage and history.

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 cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.5°F (-4.7°C)Light RainMostly CloudyAverageSlightly Low
February25.3°F (-3.7°C)Light RainMostly CloudySlightly LowAverage
March33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low
April44.8°F (7.1°C)Light RainMostly CloudyAverageAverage
May56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
June64.4°F (18.0°C)Light RainMostly SunnySlightly HighAverage
July70.5°F (21.4°C)Light RainMostly SunnySlightly HighSlightly High
August68.7°F (20.4°C)Light RainMostly SunnyAverageSlightly High
September61.9°F (16.6°C)Light RainMostly SunnySlightly HighAverage
October50.7°F (10.4°C)Light RainMostly SunnyAverageSlightly High
November38.8°F (3.8°C)Light RainMostly SunnySlightly LowAverage
December30.2°F (-1.0°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Chester

Flying into Chester, Massachusetts, you have several major airports to choose from. Bradley International Airport (BDL) in Hartford, CT, is located 45.1km away and offers nearby accommodation such as the 4-star Simsbury 1820 House and the 3.5-star Sheraton Hartford Hotel at Bradley Airport, both easily accessible. Albany International Airport (ALB) is situated 85.3km from Chester, with options like The Landing Hotel at Rivers Casino & Resort and the DoubleTree by Hilton Schenectady Downtown, both 12.9km from the airport. Worcester Regional Airport (ORH) is 91.7km away, with hotels such as Beechwood Hotel and AC Hotel by Marriott Worcester providing convenient access.

Frequently asked questions

What's the best place to stay in Chester?
La Quinta Inn & Suites by Wyndham Springfield MA, located 22.9 mi (36.8 km) from the heart of Chester, is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are Red Roof Inn PLUS+ West Springfield and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water": This holiday home rental outside of Chester is located on a river, and offers a fireplace, laundry facilities and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a stovetop and a microwave can make your holiday run smoothly. See all vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes, the majority of room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What is staying in Chester like?
Visitors can enjoy all that Chester has to offer, including the waterfalls, shopping and riverfront. Tourists can also enjoy the city's restaurants, theatres and monuments. In Chester, there are 2 hotels and other accommodation options to choose from. Find out more about Chester.
What is there to see in Chester?
A favourite place to visit is Chester Town Hall. You'll also find Glendale Falls and Pyramid Lake in the area. Take a look at what more there is to see and do in Expedia's Chester guide.
What's the weather like in Chester?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.

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