Chesterfield Hotels

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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, (126)
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
United States
Allison
The price is P4,659
P8,087 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Blooming Inn

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (818)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
The price is P6,850
P7,651 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hampton Inn Westfield

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (904)
"We left too early for breakfast. Parking was fine "
United States
Virginia
The price is P5,500
P6,144 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Quality Inn Westfield - Springfield

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (69)
"This is a brand new hotel. Everything was perfect, from check-in to check-out. We especially enjoyed the hot tub and pool. "
United States
Joan
The price is P7,199
P8,042 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (809)
"Clean room and staff was super friendly"
United States
Yuen
The price is P8,753
P9,777 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hotel On North

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is P7,513
P8,391 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hilton Garden Inn Lenox Pittsfield

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (796)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is P5,797
P7,788 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Berkshire Mountain Lodge

Inn on Boltwood

Inn on Boltwood
3.0 star property
Amherst
9.4 out of 10, Exceptional, (752)
"Room was clean and the bed was very comfortable. "
United States
Michael
Inn on Boltwood

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1002)
"Love staying on campus when we visit!"
United States
Joan
The price is P7,379
P8,309 total
includes taxes & fees
Dec 28 - Dec 29
Hotel UMass

Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (683)
"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 P8,412
P9,397 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Courtyard by Marriott Hadley Amherst

Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (718)
"great location and huge room, very nice hotel suite!"
United States
Lihong
The price is P8,286
P9,255 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Homewood Suites by Hilton Hadley Amherst

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (347)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is P5,522
P6,168 total
includes taxes & fees
Dec 29 - Dec 30
The Central Downtown Inn & Suites

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1004)
"Clean room, great staff, and good options for breakfast."
United States
nancy
The price is P6,698
P7,482 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Comfort Inn & Suites Hadley - Amherst

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (960)
"Great welcome at front desk."
United States
RAYMAN
The price is P7,730
P8,635 total
includes taxes & fees
Jan 22 - Jan 23, 2026
Hampton Inn Hadley-Amherst Area

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is P5,052
P5,643 total
includes taxes & fees
Dec 28 - Dec 29
Berkshire Inn

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
10.0 out of 10, Exceptional, (98)
"Was a wonderful inn and breakfast absolutely delicious!"
United States
Valerie
Black Walnut Inn

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (998)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is P5,181
P5,788 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"Nice place for a weekend away."
United States
Gregory
The price is P12,631
P13,351 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Harbour House Inn

Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst
3.0 star property
Northampton
9.2 out of 10, Wonderful, (1000)
"An excellent stay. Wonderfully clean, friendly front desk staff and the breakfast buffet was actually good. Will definitely stay again."
United States
Joyce
The price is P7,872
P8,793 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Fairfield Inn & Suites Springfield Northampton/Amherst

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, (143)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is P10,207
P11,402 total
includes taxes & fees
Dec 28 - Dec 29
The Trail in Adams - Berkshires’ Art Hotel
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

More cheap stays in Chesterfield

Find out more about Chesterfield

Top reasons to visit Chesterfield

  • Outdoor Adventures: Chesterfield is ideal for outdoor enthusiasts, offering skiing, water rafting, and scenic excursions in beautiful surroundings.
  • Charming Local Communities: Experience the delightful atmosphere of nearby towns with family-friendly vibes and vibrant markets.
  • Historic Attractions: Explore a mix of historic and modern colleges, as well as national and state parks.
  • Diverse Accommodation: Choose from charming hotels and unique agritourism properties, catering to all needs.
  • Recreational Opportunities: Enjoy various activities at the Westport Event Center and local shopping malls.

Find great hotels near Chesterfield

Chesterfield offers a delightful selection of accommodation options, from charming hotels to unique agritourism properties. Whether you're seeking a family-friendly retreat, a pet-friendly haven, or a business-oriented stay, you'll find establishments equipped with EV charging stations and exceptional amenities. Discover the best hotels in the area, including the renowned Chesterfield Inn, ensuring a memorable experience in this picturesque location.

  • Red Roof Inn PLUS+ West Springfield: Nestled 33.8km from Chesterfield, the Red Roof Inn PLUS+ West Springfield offers a welcoming atmosphere for LGBTQIA travellers and pet owners alike. This hotel prides itself on its inclusivity, making it a perfect choice for those seeking a friendly environment. With a variety of pet amenities, including permitted in-room stays for dogs and cats, it ensures your furry friends can enjoy the trip with you. The pet policy is designed with flexibility in mind, accommodating various needs while maintaining a comfortable setting for all guests.
  • Red Roof Inn PLUS+ South Deerfield – Amherst: Located 20.9km from Chesterfield, the Red Roof Inn PLUS+ South Deerfield – Amherst is another excellent option for pet-friendly and LGBTQIA welcoming accommodation. This hotel embodies a relaxed and inviting atmosphere, making it ideal for those travelling with pets. With amenities that allow dogs and cats in rooms and a service animal policy with waived fees, it caters to all pet lovers. The hotel's dedication to inclusivity makes it a popular choice among visitors seeking comfort and convenience during their stay.
  • Comfort Inn & Suites: Situated 24.1km from Chesterfield, Comfort Inn & Suites is designed for business travellers and families seeking a welcoming and practical lodging experience. This property stands out for its family-friendly amenities, including complimentary cribs for younger guests, ensuring a hassle-free stay for families. With its affiliation to LGBTQI travel guides, it guarantees a comfortable environment for all. Its strategic location and range of services make it a superb choice for those balancing work and leisure during their visit.

Where to stay near Chesterfield

Chesterfield, Massachusetts, offers a delightful blend of adventure and relaxation for all types of travellers. Immerse yourself in the charming atmosphere of nearby towns, where family-friendly vibes meet vibrant markets and music venues. Enjoy the clean air while exploring local shopping malls and the stunning natural surroundings. Whether you seek outdoor sports or a peaceful retreat, Chesterfield's welcoming community and picturesque landscapes promise an unforgettable experience.

  • Northampton: This vibrant city is located 17.7km from Chesterfield and is known for its rich cultural scene and outdoor adventures. Northampton offers a unique travel experience, especially for those interested in educational and recreational activities. The city is home to historic and modern colleges, providing a blend of academia and youthful energy. Visitors can enjoy skiing during the winter months, or explore various events and conferences throughout the year, making it an ideal destination for culture enthusiasts and adventure seekers alike.
  • Western Massachusetts: Just 3.2km from Chesterfield, Western Massachusetts is a picturesque region perfect for outdoor lovers. The area is particularly popular during the summer months and in October, offering breathtaking scenery, romantic getaways, and thrilling outdoor adventures. From serene lakes to majestic mountains and national state parks, the natural beauty here is unparalleled. With ample opportunities for skiing at local resorts, this destination promises an invigorating experience for those who appreciate nature’s wonders.
  • Williamsburg: Located 9.7km away from Chesterfield, Williamsburg is an outdoor enthusiast's paradise. Known for its scenic landscapes and adventurous spirit, the city attracts visitors year-round, with peak travel in the summer and early autumn. Here, you can engage in various outdoor activities, including skiing and exploring the surrounding mountains and lakes. The presence of a modern college adds a youthful vibe, making Williamsburg a lively and engaging place to visit, whether you're seeking relaxation or adventure.

Things to do near Chesterfield

Chesterfield is perfect for adventure and outdoor sports enthusiasts, offering a range of activities such as skiing at local resorts and exploring scenic town excursions. For thrill-seekers, water rafting is a must-try, while the Westport Event Center provides various recreational options. Whether you're hitting the slopes or enjoying the natural beauty, Chesterfield promises an exciting getaway.

Shopping

For a delightful shopping experience in Chesterfield, visit the local shops for unique gifts and souvenirs. If you're up for a drive, Yankee Candle Village, 20.9km away, offers a charming atmosphere, while Montague Bookmill, 22.5km away, provides a quaint, literary vibe. Holyoke Crossing, 29.0km away, is perfect for family shopping.

Recreation

Explore the serene Land of Providence, a tranquil recreational area perfect for relaxation amidst nature. Experience the artistry at Jacob's Pillow, where dance meets culture and romance. For sports enthusiasts, the Mullins Center offers an engaging atmosphere filled with excitement and energy.

Adventure

Embark on the Skyline Trail, a stunning hiking route located 16.1km from Chesterfield, offering breathtaking scenery and a true outdoor adventure. For a thrilling day of tennis, visit the Look Memorial Park Tennis Center, situated 14.5km away, where excitement awaits. In winter, the Blandford Ski Area, 22.5km distant, provides exhilarating skiing experiences.

Nightlife

In Chesterfield, the Academy of Music Theater offers a charming cultural experience, just 19.3km away, perfect for a romantic evening. For family fun, Spare Time Bowling, also 19.3km distant, provides a lively arcade atmosphere. Meanwhile, Cinemark at Hampshire Mall, 24.1km away, promises entertaining films for all ages.

*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 visit to Chesterfield, consider travelling in March or from December to January when accommodation prices are lower. Book your stay on a Tuesday, the cheapest day, and avoid Saturdays for better rates. Utilise Expedia's search tool to find eco-friendly hotels and combine your bookings for flights and activities to secure package deals. Explore the area on foot or use public transport to keep costs down, and look for free local attractions to enhance your experience without overspending.

  • 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: Utilise Expedia’s search tool to refine your choices based on your budget, preferred location, and the type of accommodation you desire. For instance, selecting the Eco-certified option will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can reduce your expenses by combining your Chesterfield hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Chesterfield

Chesterfield offers a delightful blend of adventure and outdoor pursuits, making it an ideal destination for sports enthusiasts and families alike. Visitors can explore a variety of attractions, including historic and modern colleges and universities, as well as national and state parks. Whether you seek a cultural experience or simply wish to enjoy the great outdoors, Chesterfield promises memorable activities for every type of traveller.

  • Smith College Museum of Art: Located 19.3km from Chesterfield, this art museum boasts an impressive collection that spans centuries and cultures, providing a rich cultural experience. Visitors can immerse themselves in both contemporary and classical artworks, making it a must-visit for art enthusiasts.
  • Deerfield River: Situated 24.1km away, the Deerfield River offers stunning outdoor scenery and is perfect for various recreational activities such as kayaking, fishing, and hiking. The picturesque views along the riverbanks create an idyllic backdrop for nature lovers.
  • Calvin Coolidge Presidential Library and Museum: Also 19.3km from Chesterfield, this history museum showcases the life and legacy of the 30th President of the United States. Visitors can explore fascinating exhibits that provide insight into early 20th-century American history and politics.

Best time to go to Chesterfield

The best time to visit Chesterfield is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

Chesterfield, Massachusetts, can be conveniently accessed via several major airports. Hartford, CT (BDL-Bradley International) is situated 53.1km away, with nearby accommodation options such as the 4-star Simsbury 1820 House, located 11.3km from the airport, and the Marriott Hartford Downtown, 19.3km away. Albany, NY (ALB-Albany International) lies 88.5km from Chesterfield, featuring hotels like The Landing Hotel at Rivers Casino & Resort, 12.9km from the airport, and Crowne Plaza Albany - The Desmond Hotel by IHG, just 1.6km away. Lastly, Worcester, MA (ORH-Worcester Regional) is 80.5km distant, with hotel choices including the 4-star Beechwood Hotel, located 8.0km from the airport.

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 Berkshire Mountain Lodge. See all available top hotels, or 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.
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, Chesterfield Gorge Reservation, and Westfield River. A couple of additional sights to add to your agenda are Chesterfield Public Library and Chesterfield Town Hall. 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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