Find hotels in Chesterfield, MA from $78

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Our top choices for Chesterfield hotels

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1003)
"Everything was perfect: clean room, great breakfast, courteous staff!"
United States
Tiffany
$89 nightly
The price is $101
Dec 30 - Dec 31
Total with taxes and fees
Tru by Hilton Chicopee Springfield

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, (997)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$98 nightly
The price is $109
Jan 2 - Jan 3, 2026
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2247)
"The room was clean quiet and breakfast is great!! "
United States
Amanda
$134 nightly
The price is $149
Jan 1 - Jan 2, 2026
Total with taxes and fees
D. Hotel Suites & Spa

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
West Springfield
9.6 out of 10, Exceptional, (110)
"New and still working some kinks out but overall a great stay. "
United States
Jesse
$115 nightly
The price is $132
Jan 13 - Jan 14, 2026
Total with taxes and fees
Blue – A Modern Hotel, an Ascend Collection Hotel

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1006)
"Clean room, great staff, and good options for breakfast."
United States
nancy
$114 nightly
The price is $127
Jan 4 - Jan 5, 2026
Total with taxes and fees
Comfort Inn & Suites Hadley - Amherst

Best Western Springfield West Inn

Best Western Springfield West Inn
2.5 star property
West Springfield
7.8 out of 10, Good, (1001)
"Decent breakfast"
United States
Jennifer
$93 nightly
The price is $107
Dec 30 - Dec 31
Total with taxes and fees
Best Western Springfield West Inn

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (928)
"Clean, lovely staff and breakfast "
United Kingdom
MICHAEL
$123 nightly
The price is $137
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Ellery

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (817)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
$116 nightly
The price is $130
Jan 11 - Jan 12, 2026
Total with taxes and fees
Hampton Inn Westfield

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (1000)
"nearby eateries"
United States
Majorie
$98 nightly
The price is $112
Dec 28 - Dec 29
Total with taxes and fees
Hampton Inn West Springfield

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
2.5 star property
Holyoke
9.2 out of 10, Wonderful, (598)
"Room was very clean, the breakfast was delicious!"
United States
William
$118 nightly
The price is $132
Dec 25 - Dec 26
Total with taxes and fees
Fairfield Inn & Suites Springfield Holyoke

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1001)
"Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. "
United States
Max
$85 nightly
The price is $95
Dec 28 - Dec 29
Total with taxes and fees
Red Roof Inn PLUS+ South Deerfield – Amherst

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1007)
"Love staying on campus when we visit!"
United States
Joan
$144 nightly
The price is $161
Dec 25 - Dec 26
Total with taxes and fees
Hotel UMass

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1003)
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
$83 nightly
The price is $92
Jan 11 - Jan 12, 2026
Total with taxes and fees
Quality Inn Lee - Lenox South

Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG
2.5 star property
West Springfield
8.4 out of 10, Very Good, (810)
"Great staff"
United States
JOHN
$98 nightly
The price is $112
Jan 1 - Jan 2, 2026
Total with taxes and fees
Candlewood Suites West Springfield by IHG

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
$128 nightly
The price is $143
Jan 2 - Jan 3, 2026
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield

Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield
3.0 star property
West Springfield
9.2 out of 10, Wonderful, (585)
"Room was clean and staff was super friendly "
United States
Jessuca
$118 nightly
The price is $135
Dec 28 - Dec 29
Total with taxes and fees
Courtyard by Marriott West Springfield

Hotel Northampton

Hotel Northampton
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1000)
"Very good stay"
United States
Richard
$165 nightly
The price is $184
Dec 25 - Dec 26
Total with taxes and fees
Hotel Northampton

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
$94 nightly
The price is $104
Jan 11 - Jan 12, 2026
Total with taxes and fees
Quality Inn Westfield - Springfield

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (959)
"Great welcome at front desk."
United States
RAYMAN
$130 nightly
The price is $146
Jan 13 - Jan 14, 2026
Total with taxes and fees
Hampton Inn Hadley-Amherst Area

Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (715)
"great location and huge room, very nice hotel suite!"
United States
Lihong
$141 nightly
The price is $158
Jan 5 - Jan 6, 2026
Total with taxes and fees
Homewood Suites by Hilton 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 a haven for outdoor enthusiasts, offering activities like water rafting, skiing, and exploring national parks.
  • Charming Nearby Towns: Discover delightful local towns with family-friendly atmospheres, vibrant music venues, and shopping opportunities.
  • Scenic Beauty: Enjoy the breathtaking landscapes and clean air, perfect for relaxation and rejuvenation.
  • Diverse Accommodations: Find a range of lodging options, from family-friendly to pet-friendly hotels, catering to various traveler needs.
  • Community Vibe: Experience the warm and welcoming atmosphere of Chesterfield, making it an ideal destination for all visitors.

Find great hotels near Chesterfield

Discover a range of hotel accommodations in Chesterfield, Massachusetts, designed to cater to the diverse needs of travelers. From family-friendly options to pet-friendly stays, you'll find the perfect fit for your vacation. Many hotels also offer business-centered services and amenities, including EV charging stations for electric vehicle owners. Experience a relaxing getaway in this charming town with our carefully selected lodging options.

  • Red Roof Inn PLUS+ West Springfield: Nestled 21 miles from Chesterfield, Red Roof Inn PLUS+ West Springfield is a welcoming haven for travelers seeking a pet-friendly experience with a strong commitment to inclusivity. This hotel proudly embraces LGBTQIA guests and is affiliated with LGBTQI travel guides, ensuring a comfortable stay for all. Its amenities include pet-friendly policies that allow dogs and cats, alongside a service animal policy that waives fees. With a warm atmosphere and accommodating staff, this hotel is perfect for those traveling with furry companions.
  • Red Roof Inn PLUS+ South Deerfield – Amherst: Located 13 miles from Chesterfield, Red Roof Inn PLUS+ South Deerfield – Amherst stands as an ideal choice for LGBTQIA travelers and pet lovers alike. This hotel emphasizes a welcoming environment and provides pet-friendly accommodations, allowing for a stress-free stay with your pets. Guests can enjoy the flexibility of variable pet fees and in-room access for dogs and cats, making it a convenient option for those on the go. Here, comfort meets inclusivity, ensuring a delightful vacation experience.
  • Quality Inn West Springfield: Situated 21 miles from Chesterfield, Quality Inn West Springfield is a family-friendly hotel that caters to both leisure and business travelers. With a golf-themed atmosphere, this property offers an array of business amenities, including a 24-hour business center and accessible meeting spaces, making it well-suited for corporate gatherings. Families will appreciate the thoughtful amenities for children, such as complimentary cribs and first aid kits. Quality Inn combines comfort and practicality, creating a versatile environment for every guest.

Where to stay near Chesterfield

Chesterfield, Massachusetts, offers a perfect blend of outdoor adventures and scenic beauty, making it an ideal vacation spot. Explore charming nearby towns with family-friendly atmospheres, vibrant music venues, and delightful shopping malls. Breathe in the clean air as you enjoy the welcoming vibe of the community. Whether you're seeking relaxation or excitement, Chesterfield and its surroundings promise a memorable experience for every traveler.

  • Northampton: Located 11 miles from Chesterfield, Northampton is a vibrant city known for its rich cultural scene and outdoor activities. Visitors flock here for music concerts, educational experiences, and scenic landscapes. The city boasts historic and modern colleges, making it a hub of academic and artistic endeavors. With its charming downtown area filled with eclectic shops and cafes, Northampton is perfect for those seeking a mix of urban energy and natural beauty. Don't miss the nearby lake, where you can relax or engage in water activities, especially during the peak months of April, July, and September.
  • Western Massachusetts: Just 2 miles from Chesterfield, Western Massachusetts offers a delightful escape for nature lovers and adventure seekers. This area is celebrated for its stunning scenery and outdoor recreational opportunities, including skiing and hiking in the national state parks and mountains. Visitors can immerse themselves in the beautiful landscape, particularly during the bustling summer months of July and August, as well as in October. The region is perfect for those looking to explore its natural wonders and enjoy thrilling adventures amidst breathtaking views.
  • Goshen: A charming city located 4 miles from Chesterfield, Goshen is known for its seasonal appeal, with peak visitor numbers in the summer months. This area is ideal for couples and families seeking romantic getaways or outdoor adventures. With a focus on scenic beauty, Goshen features a variety of recreational areas and resorts. Visitors can explore the local art gallery or spend time at the nearby lake and national state park, making it an attractive destination for nature enthusiasts and art lovers alike.

Things to do near Chesterfield

Chesterfield, Massachusetts, is perfect for outdoor enthusiasts seeking adventure and beautiful scenery. Visitors can enjoy activities such as water rafting, town excursions, and skiing at local ski fields. Don't miss the Westport Event Center for additional entertainment options. Whether you’re looking to explore nature or engage in thrilling sports, Chesterfield offers a variety of experiences for an unforgettable vacation.

Shopping

For a charming shopping experience in Chesterfield, visit Montague Bookmill, a unique bookstore 14 miles away. If you're up for a drive, Don Muller Gallery offers fine art 12 miles away, while Richardson's Candy Kitchen, 16 miles away, is perfect for sweet gifts and treats.

Recreation

Experience the vibrant arts at Jacob's Pillow, where you can enjoy captivating dance performances in a beautiful setting. For relaxation, head to Land of Providence, a serene recreational area perfect for unwinding. Don’t miss the Mullins Center for exciting sports events that energize and entertain.

Adventure

Experience the breathtaking views on the Skyline Trail, a hiking path located 10 miles from Chesterfield, perfect for outdoor enthusiasts. For climbing lovers, the Central Rock Climbing Center, 13 miles away, offers thrilling climbing experiences. If you enjoy winter sports, head to Blandford Ski Area, 14 miles from Chesterfield, for skiing adventures.

Nightlife

Experience the vibrant nightlife in Chesterfield by visiting the Academy of Music Theater for an enchanting show, or enjoy a fun-filled evening at Spare Time Bowling with arcade games. For more culture, check out Double Edge Theatre for a captivating performance, all within a short drive.

*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 on your trip to Chesterfield, plan your visit during the cheaper months of March or December to January, and aim for a Tuesday stay, as Saturdays are the priciest. Use Expedia to find budget-friendly accommodations by applying filters like Eco-certified hotels and sorting prices from low to high. Consider booking a package that includes flights and activities for additional savings. Joining Expedia's One Key membership can unlock exclusive discounts and allow you to earn OneKeyCash for future bookings. Look out for deals on EV parking and holiday homes to further reduce costs.

  • 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 refine your preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply arrange 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.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Chesterfield

Chesterfield, Massachusetts, is an ideal destination for outdoor enthusiasts and adventure seekers. Visitors can explore a variety of attractions, including historic and modern colleges and universities, as well as national and state parks. These points of interest cater to travelers looking for outdoor activities, cultural experiences, and family-friendly adventures, ensuring a memorable vacation for everyone.

  • Smith College: Located 11 miles from Chesterfield, Smith College is a historic institution known for its stunning architecture and vibrant cultural atmosphere. Visitors can enjoy beautiful gardens, art galleries, and a rich history that reflects the women's educational movement.
  • University of Massachusetts Amherst: Situated 16 miles away, this modern university embodies a lively city vibe, featuring contemporary campus buildings and a diverse student body. The university hosts various events and activities, making it a hub of innovation and learning.
  • Swift River: Just 4 miles from Chesterfield, the Swift River offers breathtaking scenery and ample opportunities for outdoor activities such as hiking, fishing, and picnicking amidst nature's beauty.

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

If you're planning to visit Chesterfield, Massachusetts, there are several major airports to consider flying into. Hartford, CT (BDL-Bradley Intl.) is located 33 miles away, with nearby hotel options like the DoubleTree by Hilton Hartford - Bradley Airport and Marriott Hartford Downtown. Albany, NY (ALB-Albany Intl.) is 55 miles away, offering hotels such as Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort. Lastly, Worcester, MA (ORH-Worcester Regional) is 50 miles from Chesterfield, with accommodations including Beechwood Hotel and AC Hotel by Marriott Worcester. Each airport has convenient access from these hotels, making travel hassle-free.

Frequently asked questions

When is the best time to go to Chesterfield?
The best time to visit Chesterfield is in April, when the city comes alive with vibrant spring colors and pleasant weather. During this month, temperatures typically range from the mid-50s to low 60s Fahrenheit, providing a comfortable backdrop for exploring Chesterfield's charming market square and historical sites.

As you consider your travel plans, keep in mind that the peak season runs from March to May. This is when the city experiences a lively atmosphere, with various events and activities drawing visitors eager to experience the local culture. April, in particular, offers a delightful balance of mild weather and fewer crowds compared to later spring months, allowing for a more relaxed sightseeing experience.

For those who enjoy outdoor activities, April is ideal for leisurely strolls in the picturesque parks or enjoying a canal-side picnic. The blossoming flowers and budding trees create a refreshing environment that enhances your outdoor adventures. Chesterfield's proximity to the stunning Peak District also presents exciting hiking opportunities for those looking to connect with nature.

If you're seeking a more budget-friendly option, visiting in January can provide great value, as this month typically sees lower accommodation rates and fewer tourists. However, April's pleasant climate and array of activities make it a great choice for a memorable visit.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 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 Chesterfield.
How can I save on a Chesterfield hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and Member Prices on Chesterfield hotels. Plus, you'll earn OneKeyCash™* 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.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Chesterfield hotel?
Prices for hotels in Chesterfield often vary, but you can find a great deal from $78 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 the cheapest rate.

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