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Our top choices for Chesterfield hotels

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (129 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is SAR 365
SAR 591 total
includes taxes & fees
15 Jan - 16 Jan
Blooming Inn

Inn on Boltwood

Inn on Boltwood
3.0 star property
Amherst
9.4 out of 10, Exceptional, (756 reviews)
"Idyllic New England inn…. Cozy, super clean, great restaurant on the property, roaring fireplace, great way to spend weekend with family over the holidays!"
United States
Eileen
The price is SAR 730
SAR 815 total
includes taxes & fees
14 Jan - 15 Jan
Inn on Boltwood

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (907 reviews)
"Owner was very rude at check in"
United States
Robert
The price is SAR 351
SAR 392 total
includes taxes & fees
1 Feb - 2 Feb
Quality Inn Westfield - Springfield

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (821 reviews)
"I will stay again"
United States
Jailene
The price is SAR 427
SAR 477 total
includes taxes & fees
1 Feb - 2 Feb
Hampton Inn Westfield

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1,002 reviews)
"Love staying on campus when we visit!"
United States
Joan
The price is SAR 501
SAR 563 total
includes taxes & fees
27 Jan - 28 Jan
Hotel UMass

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (73 reviews)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is SAR 460
SAR 513 total
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (686 reviews)
"The staff was helpful, available, the gym was clean and easy to use, the rooms were spacious and very clean. Great hotel"
United States
Jan
The price is SAR 570
SAR 637 total
includes taxes & fees
27 Jan - 28 Jan
Courtyard by Marriott Hadley Amherst

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
10.0 out of 10, Exceptional, (99 reviews)
"Enjoyable stay with a warm environment. Enjoyed the breakfast which was well prepared based on my order choice and request. Would stay again!"
United States
Karri
Black Walnut Inn

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is SAR 334
SAR 373 total
includes taxes & fees
23 Jan - 24 Jan
Elm Motel

Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (723 reviews)
"great location and huge room, very nice hotel suite!"
United States
Lihong
The price is SAR 520
SAR 581 total
includes taxes & fees
10 Feb - 11 Feb
Homewood Suites by Hilton Hadley Amherst

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (968 reviews)
"Staff was very friendly, room very clean"
United States
Christine
The price is SAR 483
SAR 540 total
includes taxes & fees
12 Feb - 13 Feb
Hampton Inn Hadley-Amherst Area

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (144 reviews)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is SAR 652
SAR 728 total
includes taxes & fees
14 Jan - 15 Jan
The Trail in Adams - Berkshires’ Art Hotel

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (661 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is SAR 480
SAR 536 total
includes taxes & fees
30 Jan - 31 Jan
Hilton Garden Inn Lenox Pittsfield

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.6 out of 10, Exceptional, (60 reviews)
"The property is very clean and pet friendly. The staff were very friendly and professional. I will definitely stay here again."
United States
Diana
The price is SAR 558
SAR 623 total
includes taxes & fees
27 Jan - 28 Jan
TownePlace Suites by Marriott Hadley Amherst

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (815 reviews)
"Great staff, room was huge and comfortable. "
United States
Cameron
The price is SAR 559
SAR 624 total
includes taxes & fees
15 Jan - 16 Jan
Hotel On North

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (354 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is SAR 353
SAR 394 total
includes taxes & fees
1 Feb - 2 Feb
The Central Downtown Inn & Suites

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is SAR 758
SAR 801 total
includes taxes & fees
10 Feb - 11 Feb
Harbour House Inn

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (25 reviews)
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
The price is SAR 563
SAR 629 total
includes taxes & fees
14 Jan - 15 Jan
The Revival House

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (810 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is SAR 370
SAR 497 total
includes taxes & fees
2 Feb - 3 Feb
Berkshire Mountain Lodge

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1,003 reviews)
"Clean room, great staff, and good options for breakfast."
United States
nancy
The price is SAR 433
SAR 483 total
includes taxes & fees
12 Feb - 13 Feb
Comfort Inn & Suites Hadley - Amherst
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 Chesterfield attractions

Top Chesterfield Hotel Reviews

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Hotels in Chesterfield with star-rating

Find out more about Chesterfield

Top reasons to visit Chesterfield

  • Outdoor Adventures: Chesterfield is ideal for outdoor enthusiasts, offering activities like skiing and water rafting amidst stunning scenery.
  • Scenic Beauty: Experience the breathtaking landscapes and clean air in this charming market town, perfect for relaxation.
  • Cultural Experiences: Explore historic colleges and vibrant nearby towns with unique shopping and local music venues.
  • Family-Friendly Activities: Enjoy a variety of attractions that cater to families, ensuring memorable experiences for everyone.
  • Diverse Accommodations: Choose from a range of lodging options, including pet-friendly hotels and eco-conscious stays.

Find great hotels near Chesterfield

Discover a range of hotel accommodations in Chesterfield, Massachusetts, ideal for both business and leisure travelers. From pet-friendly options to family-oriented stays, you'll find the perfect place to relax. Many hotels also feature EV charging stations, catering to eco-conscious guests. Whether you're seeking a top-rated hotel or a charming inn, Chesterfield offers a variety of lodging experiences to meet your needs.

  • Red Roof Inn PLUS+ West Springfield: Experience a welcoming atmosphere at Red Roof Inn PLUS+ West Springfield, located 33.8km from Chesterfield. This hotel stands out for its pet-friendly policy and LGBTQIA inclusivity, making it an excellent choice for diverse travelers. With a commitment to comfort, the property allows pets with certain restrictions and offers amenities tailored for furry companions. Guests can enjoy a cozy stay while knowing they are in an inclusive environment, ideal for anyone seeking a home away from home.
  • Red Roof Inn PLUS+ South Deerfield – Amherst: Just 20.9km from Chesterfield, Red Roof Inn PLUS+ South Deerfield – Amherst offers an inviting escape for guests looking for pet-friendly and LGBTQIA welcoming accommodations. The hotel emphasizes comfort and understanding, allowing pets in rooms with applicable policies. The property’s affiliation with LGBTQI travel guides highlights its commitment to inclusivity. Guests can relax in a friendly atmosphere while enjoying facilities that cater to both pet owners and those seeking a warm, welcoming environment.
  • Quality Inn West Springfield: Ideal for families and business travelers, Quality Inn West Springfield is located 33.8km from Chesterfield. The hotel features a golf theme that appeals to enthusiasts, offering guests an opportunity to enjoy a round of golf during their stay. With amenities designed for children, including free cribs and first aid kits, families will find it a comforting choice. The property’s focus on both leisure and business needs ensures a balanced experience for all visitors.

Where to stay near Chesterfield

Chesterfield, Massachusetts, offers a delightful blend of outdoor adventure and scenic beauty, perfect for family-friendly vacations. Explore charming nearby towns with vibrant atmospheres, including local music venues and unique shopping malls. Enjoy clean air and the warmth of friendly people as you immerse yourself in this relaxing market town. Whether seeking adventure or a peaceful retreat, Chesterfield and its surrounding areas promise an unforgettable experience for every traveler.

  • Northampton: A vibrant city located 17.7km from Chesterfield, Northampton is known for its rich cultural scene and outdoor activities. With a steady influx of visitors throughout the year, this city peaks in popularity during the months of April, July, and September. Travelers can immerse themselves in educational experiences at historic and modern colleges or enjoy the excitement of local ski fields. The city's landmarks, including charming universities and event venues, provide a blend of culture and fun that makes Northampton a must-visit destination.
  • Western Massachusetts: Just 3.2km away from Chesterfield, Western Massachusetts is a picturesque region that attracts visitors year-round, with peaks in July to August and October. Known for its stunning scenery and romantic outdoor experiences, this area offers a wealth of activities such as skiing at local resorts and exploring nearby national parks. Adventure seekers can revel in the natural beauty of lakes and mountains, making it an ideal spot for nature lovers and those looking for a serene escape.
  • Williamsburg: Located 9.7km from Chesterfield, Williamsburg is a charming city popular for its family-friendly outdoor adventures. With a steady number of visitors year-round, the city sees a surge in travelers during June to July and September. Families can enjoy various educational activities and skiing experiences, all while soaking in the beauty of nearby mountains and lakes. Williamsburg's inviting atmosphere and array of outdoor pursuits make it an excellent choice for those seeking adventure and quality time with loved ones.

Things to do near Chesterfield

Chesterfield, Massachusetts, is perfect for outdoor and adventure enthusiasts. Visitors can enjoy activities at the local ski field and resort, while the Westport Event Center offers exciting town excursions. For those seeking more thrill, water rafting is also available. Experience the beautiful scenery and engage in various outdoor adventures during your stay in this charming town.

Shopping

Chesterfield offers charming shopping experiences. Visit Don Muller Gallery for unique art, only 19.3km away. If you're up for a drive, Yankee Candle Village and Montague Bookmill, located 13 and 22.5km away respectively, provide delightful options for gifts and souvenirs in lovely settings.

Recreation

Experience tranquility at Land of Providence, only 16.1km from Chesterfield, where you can unwind in serene nature. For a cultural escape, head to Jacob's Pillow, 27.4km away, to enjoy captivating dance performances. If you're in the mood for sports, catch an event at Mullins Center, located 25.7km from Chesterfield.

Adventure

Embark on the Skyline Trail for a breathtaking hiking experience, located 16.1km from Chesterfield, where scenic views and outdoor adventure await. For winter sports enthusiasts, the Blandford Ski Area, 22.5km away, offers thrilling skiing opportunities. Additionally, challenge yourself at the Central Rock Climbing Center, located 20.9km from town.

Nightlife

In Chesterfield, the Academy of Music Theater offers a romantic and cultural experience just 19.3km away, while the Double Edge Theatre provides an intimate atmosphere with engaging performances. For a fun adventure, head to Spare Time Bowling, also 19.3km away, where you can enjoy arcade games and bowling excitement.

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

Booking tips and Expedia advantages for Chesterfield

To save money during your trip to Chesterfield, consider visiting in March or between December and January, when accommodation prices are lower compared to the peak summer months. Booking your stay for a Tuesday instead of a Saturday can also help reduce costs. Use Expedia’s search tool to filter for budget-friendly and eco-certified hotels, and consider bundling your hotel, flights, and activities for additional savings. Don’t forget to look for deals on electric vehicle parking and holiday home rentals 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 Chesterfield 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 Chesterfield is Tuesday. The most expensive day to stay in Chesterfield is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to tailor your preferences, such as your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified option will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Chesterfield hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Chesterfield

Chesterfield, Massachusetts, is perfect for outdoor enthusiasts and adventure seekers, boasting stunning scenery and a variety of attractions. Visitors can explore historic and modern colleges and universities, as well as nearby national and state parks. The area's points of interest cater to families and culture lovers alike, offering memorable experiences that combine nature and history in a charming setting.

  • Smith College: A prestigious women's college, Smith College boasts stunning architecture and beautiful gardens. Located 17.7km from Chesterfield, it offers a rich cultural experience with art galleries, performances, and lectures that reflect its historic charm.
  • University of Massachusetts Amherst: This vibrant university, 25.7km away, is known for its innovative programs and lively atmosphere. With modern facilities and a strong sense of community, it provides a dynamic city vibe perfect for exploring student life and various cultural events.
  • Chesterfield Gorge: Nestled within Chesterfield, this breathtaking canyon offers outdoor adventure and scenic beauty. Hike the trails to enjoy stunning views of the gorge and the surrounding nature, making it a perfect spot for nature lovers and thrill-seekers alike.

Best time to go to Chesterfield

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.9°F (-3.4°C)Light RainMostly SunnyLowSlightly Low
February27.3°F (-2.6°C)Light RainMostly SunnyAverageAverage
March35.2°F (1.8°C)Light RainMostly SunnyHighSlightly Low
April47.1°F (8.4°C)Light RainMostly SunnyHighAverage
May58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageAverage
July72.7°F (22.6°C)Light RainMostly SunnyHighSlightly High
August70.9°F (21.6°C)Light RainMostly SunnyAverageSlightly High
September63.7°F (17.6°C)Light RainMostly SunnyAverageAverage
October52.3°F (11.3°C)Light RainMostly SunnyAverageSlightly High
November40.3°F (4.6°C)Light RainMostly SunnyLowAverage
December32.0°F (0.0°C)Light RainMostly SunnyLowSlightly Low

The nearest major airports for your trip to Chesterfield

For your visit to Chesterfield, Massachusetts, you can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is 53.1km away, with nearby hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport, and the Marriott Hartford Downtown, 19.3km away. ALBany, NY (ALB-Albany Intl.) is 88.5km away, featuring options such as the Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 12.9km from the airport. Worcester, MA (ORH-Worcester Regional) is 80.5km away, with hotels like Beechwood Hotel, located 8.0km from the airport. Each hotel provides convenient access to their respective airports.

Frequently asked questions

Where is the best place to stay in Chesterfield?
Located 14.5 mi (23.3 km) from the heart of Chesterfield, D. Hotel Suites & Spa is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are Holiday Inn & Suites Pittsfield-Berkshires by IHG and Quality Inn West Springfield. See all available top hotels, or vacation rentals in Chesterfield.
What are some of the best vacation rentals that Chesterfield has to offer?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: Visitors like this Chesterfield vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. See all vacation rentals in Chesterfield.
If I need to cancel my hotel reservation in Chesterfield, will I receive a refund?
Yes, most 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 non-refundable reservation, you may still be able to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chesterfield.
Where can I learn more about changing or cancelling my trip to Chesterfield?
For additional details about rescheduling or cancelling your trip to Chesterfield, click here.
Where is the best place to stay close to Chesterfield Gorge?
Fiddlehead Inn is one of the top choices for your stay based on our traveler data, and this 3-star inn offers a restaurant and free parking. It's located 2.9 mi (4.7 km) from Chesterfield Gorge. Another good choice is Charming Farmhouse - quiet, private & peaceful, located 3 mi (4.9 km) away.
What's the best hotel for staying near Logan International Airport (BOS)?
Hilton Boston Logan Airport is a popular 4-star hotel featuring a restaurant and an indoor pool. It's located a short 0.2 mi (0.4 km) from Logan Intl. Airport. Other accommodations close to the airport are Hyatt Regency Boston Harbor and Embassy Suites Boston Logan Airport.
What is staying in Chesterfield like?
Visitors can enjoy all that Chesterfield has to offer including the restaurants, shopping, and parks. There are 487 hotels and other accommodations in the surrounding area. Find out more about Chesterfield.
What should I see while I'm in Chesterfield?
Natural beauty is on display at Chesterfield Gorge, Knightville Dam & Reservation, and Westfield River. A couple of additional sights to add to your agenda are Krug Sugarbush and Chesterfield Public Library. Check out what more to see and do in Expedia's Chesterfield guide.
What's the weather like in Chesterfield?
The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chesterfield are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.

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