Find hotels in Chesterfield, MA from AED 290

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Compare 485 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Hotel UMass

2.5 star property
Amherst
8.8 out of 10, Excellent, (1001)
"Great on campus location!"
United States
Shuhui
The price is AED 461
AED 519 total
includes taxes & fees
21 Dec - 22 Dec
Hotel UMass

Inn on Boltwood

3.0 star property
Amherst
9.4 out of 10, Exceptional, (747)
"Room was clean and the bed was very comfortable. "
United States
Michael
Inn on Boltwood

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is AED 335
AED 374 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (979)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AED 337
AED 377 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Candlewood Suites West Springfield by IHG

2.5 star property
West Springfield
8.4 out of 10, Very Good, (791)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is AED 262
AED 299 total
includes taxes & fees
7 Dec - 8 Dec
Candlewood Suites West Springfield by IHG

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (803)
"Clean room and staff was super friendly"
United States
Yuen
The price is AED 490
AED 547 total
includes taxes & fees
22 Dec - 23 Dec
Hotel On North

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (777)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge

Red Roof Inn PLUS+ West Springfield

2.5 star property
West Springfield
6.8 out of 10, (1001)
"Great like always "
United States
Sharee
The price is AED 311
AED 356 total
includes taxes & fees
11 Dec - 12 Dec
Red Roof Inn PLUS+ West Springfield

River Valley Inn

2.0 star property
West Hatfield
8.6 out of 10, Excellent, (98)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is AED 400
AED 447 total
includes taxes & fees
7 Dec - 8 Dec
River Valley Inn

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2276)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is AED 314
AED 365 total
includes taxes & fees
28 Dec - 29 Dec
D. Hotel Suites & Spa

Quality Inn West Springfield

2.5 star property
West Springfield
7.0 out of 10, Good, (1001)
"Room and staff were good "
United States
George
The price is AED 291
AED 334 total
includes taxes & fees
1 Jan - 2 January 2026
Quality Inn West Springfield

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
Northampton
9.2 out of 10, Wonderful, (1005)
"Clean room great breakfast selections would stay here again"
United States
Mary
The price is AED 459
AED 513 total
includes taxes & fees
21 Dec - 22 Dec
Fairfield Inn & Suites Springfield Northampton/Amherst

Courtyard by Marriott Hadley Amherst

3.0 star property
Hadley
9.0 out of 10, Wonderful, (681)
"Nice and quiet and conveniently located very close to UMass"
United States
Connor
The price is AED 525
AED 587 total
includes taxes & fees
17 Dec - 18 Dec
Courtyard by Marriott Hadley Amherst

Courtyard by Marriott West Springfield

3.0 star property
West Springfield
9.2 out of 10, Wonderful, (576)
"Room was clean and staff was super friendly "
United States
Jessuca
The price is AED 434
AED 497 total
includes taxes & fees
7 Dec - 8 Dec
Courtyard by Marriott West Springfield

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 star property
West Springfield
9.6 out of 10, Exceptional, (98)
"Great staff super nice beautiful hotel lots of parking "
United States
Yovelys
The price is AED 399
AED 456 total
includes taxes & fees
25 Dec - 26 Dec
Blue – A Modern Hotel, an Ascend Collection Hotel

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1000)
"Clean room and good breakfast "
United States
Kelly
The price is AED 333
AED 372 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn

Comfort Inn & Suites

2.5 star property
Hadley
9.2 out of 10, Wonderful, (1002)
"Room was spotless and the amenities were great. "
United States
kathleen
The price is AED 455
AED 508 total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites

Hampton Inn West Springfield

2.5 star property
West Springfield
8.2 out of 10, Very Good, (1001)
"nearby eateries"
United States
Majorie
The price is AED 379
AED 434 total
includes taxes & fees
11 Dec - 12 Dec
Hampton Inn West Springfield

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is AED 328
AED 366 total
includes taxes & fees
7 Dec - 8 Dec
The Central Downtown Inn & Suites

Homewood Suites by Hilton Hadley Amherst

3.0 star property
Hadley
9.4 out of 10, Exceptional, (708)
"Clean room, spacious room, nice staff, and good location for our trip. "
United States
Susan
The price is AED 520
AED 581 total
includes taxes & fees
4 Jan - 5 January 2026
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

More cheap stays in Chesterfield

Hotels in Chesterfield with star-rating

Find out more about Chesterfield

Top reasons to visit Chesterfield

  • Outdoor Adventures: Chesterfield offers thrilling skiing, water rafting, and scenic hiking opportunities, perfect for adventure enthusiasts.
  • Family-Friendly Activities: The town features a variety of family-oriented attractions and outdoor sports, ensuring fun for all ages.
  • Charming Accommodations: Enjoy a range of hotels and inns, including pet-friendly and eco-conscious options with EV charging stations.
  • Vibrant Local Culture: Explore nearby neighborhoods filled with music venues, shops, and a welcoming atmosphere.
  • Beautiful State Parks: Experience the stunning natural beauty of Chesterfield's state parks, perfect for relaxation and exploration.

Find great hotels near Chesterfield

Discover the charm of Chesterfield, Massachusetts, with a variety of hotel accommodations designed to cater to every traveler's needs. Whether you’re seeking a family-friendly getaway, a pet-friendly retreat, or a business-focused stay, you’ll find options that include EV charging stations for eco-conscious travelers. Experience the best of Chesterfield with welcoming inns and hotels that provide comfort and convenience for an unforgettable vacation.

  • Red Roof Inn PLUS+ West Springfield: Embrace a welcoming atmosphere at Red Roof Inn PLUS+ West Springfield, just 33.8km from Chesterfield. This hotel is perfect for travelers seeking a pet-friendly and LGBTQIA-friendly experience. The property boasts a commitment to inclusivity and comfort, making it an ideal choice for all guests. With amenities that cater to your furry companions, including variable fees and service animal waivers, you can relax knowing your pets are accommodated. Enjoy a stay that celebrates diversity in a cozy setting.
  • Red Roof Inn PLUS+ South Deerfield – Amherst: Located 20.9km from Chesterfield, Red Roof Inn PLUS+ South Deerfield – Amherst offers a delightful blend of comfort and convenience. Ideal for pet owners and LGBTQIA travelers, this hotel ensures a welcoming environment for all. Guests can take advantage of the pet-friendly policies, allowing pets in rooms and providing necessary amenities with variable fees. This property’s affiliation with LGBTQI travel guides highlights its commitment to inclusivity, making it a favored destination for diverse travelers.
  • Quality Inn West Springfield: Situated 33.8km from Chesterfield, Quality Inn West Springfield is tailored for business travelers and families alike. The hotel features a golf-themed experience, perfect for guests looking to unwind with a round of golf. Families will appreciate the thoughtful amenities, such as complimentary cribs and first aid kits, ensuring a comfortable stay for guests of all ages. With a focus on convenience and recreation, this hotel is an excellent choice for your family vacation.

Where to stay near Chesterfield

Chesterfield, Massachusetts, offers a delightful blend of adventure and relaxation for every traveler. Enjoy outdoor sports and family-friendly activities in the scenic landscapes surrounding the town. Explore nearby neighborhoods for vibrant music venues and charming shopping malls while soaking in the friendly atmosphere. Experience the clean air and welcoming vibe of this market town, making it a perfect base for your vacation adventures.

  • Northampton: A vibrant city located 17.7km from Chesterfield, Northampton is a cultural hub known for its lively arts scene and outdoor adventures. Visitors flock to this area throughout the year, with peak travel in April, July, and September. The city boasts historic and modern colleges, making it an educational hotspot. Engage in a range of activities, from skiing in the nearby fields to exploring local galleries and theaters. With its mix of scenic parks and cultural venues, Northampton promises a rich travel experience that blends education, adventure, and outdoor exploration.
  • Western Massachusetts: Only 3.2km from Chesterfield, Western Massachusetts offers a picturesque landscape perfect for outdoor enthusiasts. This region attracts visitors year-round, particularly during the summer and fall, with peak travel in July and October. Known for its stunning scenery, visitors can enjoy skiing at local resorts or hiking in the nearby mountains and state parks. With serene lakes and breathtaking views, Western Massachusetts is ideal for romantic getaways and nature retreats, ensuring a memorable experience for all who visit.
  • Williamsburg: Situated 9.7km from Chesterfield, Williamsburg is a charming city that captivates with its outdoor adventures and scenic beauty. The area sees a steady influx of travelers, peaking in the summer months of June and July. Known for its educational institutions and skiing opportunities, visitors can enjoy a range of activities from exploring local lakes to hitting the slopes. With its picturesque mountains and inviting atmosphere, Williamsburg is a fantastic destination for those seeking adventure and natural beauty.

Things to do near Chesterfield

Chesterfield, Massachusetts, is perfect for adventure and outdoor activities. Visitors can enjoy skiing at local resorts, experience thrilling water rafting, and explore town excursions. Don't miss the Westport Event Center for additional entertainment options. Whether you're hitting the slopes or seeking a relaxing day on the water, Chesterfield offers a range of exciting activities for an unforgettable vacation.

Shopping

For a unique shopping experience in Chesterfield, visit Yankee Candle Village, located 20.9km away, known for its delightful candles. If you're up for a drive, check out Montague Bookmill, 22.5km away, for books and gifts, or Don Muller Gallery, 19.3km away, for local art.

Recreation

Explore the serene Land of Providence, where you can unwind in nature and enjoy rejuvenating outdoor activities. At Jacob's Pillow, immerse yourself in captivating dance performances that blend romance and culture. For sports enthusiasts, the Mullins Center offers thrilling events in a vibrant atmosphere.

Adventure

Embark on the Skyline Trail for an invigorating hike surrounded by breathtaking scenery, located 16.1km from Chesterfield. Enjoy thrilling skiing at Blandford Ski Area, 22.5km away, or challenge yourself at the Central Rock Climbing Center, situated 20.9km from town for a fun climbing experience.

Nightlife

Experience the vibrant nightlife in Chesterfield by visiting the Academy of Music Theater for captivating performances, or enjoy family fun at Spare Time Bowling's arcadeAdventureZone. For a unique cultural experience, don't miss Double Edge Theatre, where romance and entertainment await just a few miles away.

*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 traveling in March or from December to January when hotel prices are lower, and avoid peak months like July and August. Book your stay on a Tuesday for the best rates, and use Expedia's search tool to find budget-friendly accommodations by sorting options from lowest to highest price. Combine your hotel, flight, and activities into an Expedia package for additional savings. Take advantage of free activities like hiking in the scenic outdoors, and explore public transport options to keep travel costs down.

  • 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 customize your options based on your budget, desired location, and preferred hotel type. 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 hotel reservation in Chesterfield with your flights and activities by choosing an Expedia package.

Find the best attractions in and around Chesterfield

Chesterfield is perfect for adventure seekers and outdoor enthusiasts, offering a blend of historic and modern colleges, as well as beautiful state parks. Visitors can enjoy a variety of activities that cater to families and culture lovers alike, ensuring a memorable experience in this charming town. Whether you're exploring the great outdoors or delving into local history, Chesterfield has something for everyone.

  • Smith College: Nestled in Northampton, this historic college exudes charm with its beautiful architecture and lush gardens. Visitors can enjoy art exhibitions and stroll through the vibrant campus, soaking in the rich culture and academic atmosphere.
  • University of Massachusetts Amherst: A modern university with a lively city vibe, UMass Amherst offers a dynamic environment. Explore its expansive campus, enjoy diverse dining options, and experience the vibrant student life that brings energy to the area.
  • Chesterfield Gorge: This stunning canyon offers breathtaking scenery and outdoor adventures. Hike along scenic trails, take in the natural beauty, and immerse yourself in the tranquility of the surrounding wilderness.

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

To reach Chesterfield, Massachusetts, you have several airport options. Bradley International Airport (BDL) in Hartford, CT, is 53.1km away and offers nearby accommodations such as the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport, and the Marriott Hartford Downtown, 19.3km away. Albany International Airport (ALB) is located 88.5km from Chesterfield, with excellent hotel choices like the Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 12.9km from the airport. Lastly, Worcester Regional Airport (ORH) is 80.5km away, with options like Beechwood Hotel and AC Hotel by Marriott, both within 8.0km of 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 Berkshire Mountain Lodge 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?
Peace and quiet on the lake: Visitors like this Chesterfield vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind. 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 483 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 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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