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Our top choices for Chesterfield hotels

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (127 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
The price is NT$3,486
NT$3,894 total
includes taxes & fees
Apr 12 - Apr 13
River Valley Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is NT$3,486
NT$3,894 total
includes taxes & fees
Apr 19 - Apr 20
Quality Inn Lee - Lenox South

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (840 reviews)
"We had an excellent experience all around. "
United States
Jennifer
The price is NT$3,773
NT$4,215 total
includes taxes & fees
Apr 19 - Apr 20
Hampton Inn Westfield

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, (1,001 reviews)
"Comfy bed, nice front desk staff."
United States
Christina
The price is NT$2,792
NT$3,118 total
includes taxes & fees
Apr 14 - Apr 15
Red Roof Inn PLUS+ South Deerfield – Amherst

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (625 reviews)
"We enjoyed our 3 nights it was quiet and very clean "
United States
Joanne
The price is NT$4,062
NT$4,537 total
includes taxes & fees
Apr 22 - Apr 23
Fairfield Inn & Suites Springfield Holyoke

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,001 reviews)
"Best hotel in area."
United States
William
The price is NT$3,642
NT$4,132 total
includes taxes & fees
May 4 - May 5
Tru by Hilton Chicopee Springfield

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2,231 reviews)
"Very clean, comfortable, and quiet hotel. We enjoyed our visit."
United States
Larry
The price is NT$4,620
NT$5,367 total
includes taxes & fees
Apr 21 - Apr 22
D. Hotel Suites & Spa

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (27 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 NT$4,796
NT$5,357 total
includes taxes & fees
Apr 21 - Apr 22
The Revival House

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (896 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is NT$3,153
NT$4,236 total
includes taxes & fees
Apr 20 - Apr 21
Berkshire Mountain Lodge

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
9.8 out of 10, Exceptional, (112 reviews)
"Beautiful Inn. Love the old brick front and antiques. The staff was amazing, breakfast was delicious and the rooms were spotless. The molasses cookies at check in were a bonus. Loved our stay here. "
United States
Rosemarie
The price is NT$5,604
NT$6,260 total
includes taxes & fees
Apr 27 - Apr 28
Black Walnut Inn

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.8 out of 10, Exceptional, (77 reviews)
"The check in staff were amazing "
United States
mandeep
The price is NT$4,862
NT$5,431 total
includes taxes & fees
Apr 19 - Apr 20
TownePlace Suites by Marriott Hadley Amherst

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (919 reviews)
"Everything clean "
United States
GLADYS
The price is NT$3,022
NT$3,375 total
includes taxes & fees
Apr 26 - Apr 27
Quality Inn Westfield - Springfield

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1,011 reviews)
"Clean and great breakfast. Friendly staff!"
United States
Kim
The price is NT$4,337
NT$4,844 total
includes taxes & fees
Apr 20 - Apr 21
Comfort Inn & Suites Hadley - Amherst

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
The price is NT$2,994
NT$4,911 total
includes taxes & fees
Apr 12 - Apr 13
Blooming Inn

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (999 reviews)
"Very good place to stay"
United States
Gloria
The price is NT$3,380
NT$3,869 total
includes taxes & fees
Apr 19 - Apr 20
Hampton Inn West Springfield

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1,004 reviews)
"Very good service and nice stay. "
United States
Deepak
The price is NT$4,017
NT$4,532 total
includes taxes & fees
Apr 12 - Apr 13
Hotel UMass

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, (87 reviews)
"New hotel clean and nice. Heated pool and hot tub a bonus. Timely breakfast for early departures- great on demand coffee. Added bonus they have a car charger."
United States
Charline
The price is NT$3,774
NT$4,216 total
includes taxes & fees
Apr 16 - Apr 17
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Best Western Springfield West Inn

Best Western Springfield West Inn
2.5 star property
West Springfield
7.8 out of 10, Good, (1,001 reviews)
"Very safe place "
United States
Madinakhon
The price is NT$2,987
NT$3,419 total
includes taxes & fees
Apr 19 - Apr 20
Best Western Springfield West Inn

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,006 reviews)
"Really liked staying here and will come back when I am in the area again!"
United States
William
The price is NT$5,002
NT$5,587 total
includes taxes & fees
Apr 29 - Apr 30
The Ellery

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (240 reviews)
"Found dead flies in the beds and the sheets were stained. I would not expect much from an inexpensive room but I do expect it to be clean."
United States
Heidi
The price is NT$2,445
NT$2,731 total
includes taxes & fees
Apr 21 - Apr 22
Rodeway Inn
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 Adventure: Chesterfield is perfect for skiing, water rafting, and exploring national and state parks, catering to adventure seekers.
  • Charming Towns: Discover picturesque market towns nearby, offering a friendly atmosphere and local charm.
  • Cultural Experiences: Visit historic colleges and universities, and enjoy local music venues for a taste of the community.
  • Family-Friendly Activities: Chesterfield provides a variety of fun options for families, ensuring everyone has a memorable visit.
  • Diverse Accommodations: Choose from family-friendly hotels to unique agritourism properties, all equipped with modern amenities.

Find great hotels near Chesterfield

Explore a variety of lodging options in Chesterfield, Massachusetts, perfect for both business and leisure travelers. From family-friendly accommodations to pet-friendly stays, you'll find hotels equipped with modern amenities, including EV charging stations. Whether you're seeking the best hotels or charming agritourism properties, Chesterfield offers a unique vacation experience tailored to your needs.

  • Red Roof Inn PLUS+ West Springfield: Experience a warm and welcoming atmosphere at Red Roof Inn PLUS+ West Springfield, located 33.8km from Chesterfield. This hotel is perfect for travelers seeking a pet-friendly and LGBTQIA-friendly environment. The property proudly partners with LGBTQI travel guides, ensuring an inclusive experience for all guests. Amenities include in-room pet accommodations for dogs and cats, with specific policies for service animals. Enjoy a comfortable stay with modern conveniences and easy access to local attractions, making it an ideal choice for those traveling with furry companions.
  • Red Roof Inn PLUS+ South Deerfield – Amherst: Situated 20.9km from Chesterfield, Red Roof Inn PLUS+ South Deerfield – Amherst offers a cozy retreat for travelers looking for a pet-friendly and LGBTQIA-welcoming getaway. This hotel is also affiliated with LGBTQI travel guides, emphasizing its commitment to inclusivity. Guests can enjoy the convenience of in-room pet policies that allow dogs and cats, ensuring your four-legged friends feel at home. With its welcoming atmosphere and modern amenities, this hotel is a great choice for those wanting to explore the beautiful surrounding area.
  • Quality Inn West Springfield: Located 33.8km from Chesterfield, Quality Inn West Springfield caters to business travelers, families, and pet owners alike. This hotel offers essential amenities for children, including free cribs and a first aid kit, ensuring a family-friendly experience. Pets are welcome, with specific policies for dogs, making it a suitable choice for guests traveling with their furry friends. The hotel balances comfort and functionality, providing a reliable stay with easy access to local businesses and attractions, making it perfect for both work and play.

Where to stay near Chesterfield

Chesterfield, Massachusetts, offers an enchanting blend of adventure and relaxation, perfect for outdoor enthusiasts and families alike. Explore nearby charming market towns, enjoy clean air, and embrace the friendly atmosphere. Don't miss the local music venues and shopping malls, where you can experience the vibrant community. With its mix of family-friendly vibes and outdoor activities, Chesterfield is an ideal destination for travelers seeking a memorable getaway.

  • Northampton: Located 17.7km from Chesterfield, Northampton is a vibrant city known for its rich cultural scene and outdoor adventures. With visitor numbers peaking in April, July, and September, the city offers an engaging atmosphere year-round. Travelers flock here for its historic and modern colleges, along with opportunities for skiing and various outdoor activities. The local landmarks, including educational institutions and event venues, provide a unique experience for visitors eager to explore art, history, and nature.
  • Western Massachusetts: Just 3.2km away from Chesterfield, Western Massachusetts is a picturesque region perfect for outdoor enthusiasts. With a peak travel season in July and August, it invites visitors to enjoy its stunning scenery and romantic settings. The area is renowned for its ski fields and resorts, making it a winter wonderland during the colder months. Local attractions such as lakes, mountains, and national state parks provide ample opportunities for hiking, skiing, and enjoying the natural beauty of the landscape.
  • Williamsburg: Located 9.7km from Chesterfield, Williamsburg is a charming city that attracts visitors seeking adventure and scenic views. With travel peaks in June, July, and September, it offers a variety of outdoor experiences, including skiing and exploring local mountains. The proximity to modern colleges and beautiful lakes enhances its appeal. Whether you're hiking or simply enjoying the breathtaking landscapes, Williamsburg provides a perfect backdrop for a memorable vacation.

Things to do near Chesterfield

Chesterfield, Massachusetts, is an ideal destination for adventure and outdoor activities. Visitors can enjoy skiing at local resorts, water rafting for an exhilarating experience, and excursions to explore the charming town. The Westport Event Center offers additional recreational options, ensuring a fun-filled vacation for sports enthusiasts and nature lovers alike.

Shopping

For a unique shopping experience in Chesterfield, visit Montague Bookmill, a charming bookstore 22.5km away. If you're up for a drive, Don Muller Gallery, located 19.3km away, offers stunning local art, while Richardson's Candy Kitchen, 25.7km away, is perfect for sweet treats and gifts.

Recreation

Explore the serene Land of Providence, a recreational area perfect for relaxation and rejuvenation, just 16.1km from Chesterfield. For a cultural experience, visit Jacob's Pillow, a renowned dance venue 27.4km away, offering romance and entertainment. Catch a thrilling game at Mullins Center, 25.7km away, for sports vibes.

Adventure

Experience the breathtaking views on the Skyline Trail, a hiking paradise located 16.1km from Chesterfield. For winter sports enthusiasts, the Blandford Ski Area, situated 22.5km away, offers thrilling skiing adventures. Meanwhile, the Central Rock Climbing Center, 20.9km from Chesterfield, provides an exhilarating climbing experience for all skill levels.

Nightlife

Experience the vibrant nightlife in Chesterfield with a visit to the Academy of Music Theater for a romantic show, or enjoy family fun at Spare Time Bowling. For a unique performance, check out the Double Edge Theatre, where culture and entertainment come to life.

*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, consider visiting during the cheaper months of March and December to January, and aim for a Tuesday stay, as it’s the least expensive day. Utilize Expedia to find budget-friendly accommodations by filtering for the best deals, including package options that combine flights and hotel stays. Additionally, explore free local activities and take advantage of public transport to minimize costs. Keep an eye out for special deals on holiday homes and EV parking to enhance your experience while keeping expenses low.

  • 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 options according to your budget, desired location, and preferred hotel category. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can potentially save money by booking a package through Expedia that combines your Chesterfield hotel stay with your flights and activities.

Find the best attractions in and around Chesterfield

Chesterfield, Massachusetts, is an ideal destination for adventure seekers and outdoor enthusiasts. Visitors can explore a variety of attractions, including historic and modern colleges and universities, as well as national and state parks. Whether you're looking for outdoor activities, cultural experiences, or family-friendly fun, Chesterfield offers a diverse range of points of interest that will make your visit memorable.

  • Smith College: Explore the charming campus of Smith College, a historic institution rich in culture. With stunning gardens, art galleries, and unique architecture, it's a perfect spot for leisurely strolls and admiring the academic atmosphere.
  • University of Massachusetts Amherst: Experience the vibrant energy of UMass Amherst, a thriving modern university. Enjoy the lively campus life, diverse dining options, and cultural events, all set against a backdrop of contemporary architecture in a bustling college town.
  • Chesterfield Gorge: Discover the breathtaking beauty of Chesterfield Gorge, a natural wonder offering scenic views and outdoor adventures. Hike along the trails, enjoy the tranquility of the gorge, and witness the stunning landscapes that change with the seasons.

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 visit Chesterfield, Massachusetts, you can fly into three major airports. Bradley International Airport (BDL) in Hartford, CT is 53.1km away and offers nearby hotels such as the DoubleTree by Hilton Hartford – Bradley Airport, 1.6km from the airport, and Simsbury 1820 House, 11.3km away. Albany International Airport (ALB) is 88.5km from Chesterfield, with options like Park Manor Hotel and The Landing Hotel at Rivers Casino, both 12.9km away. Lastly, Worcester Regional Airport (ORH) is 80.5km distant, featuring hotels like Beechwood Hotel and AC Hotel by Marriott, both within 8.0km. Each hotel provides convenient access to its respective 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 Comfort Inn & Suites Hadley - Amherst 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.
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. In Chesterfield, there are 2 hotels and other accommodations to choose from. Find out more about Chesterfield.
What should I see while I'm in Chesterfield?
Natural beauty is on display at Chesterfield Gorge, Westfield River, and Knightville Dam & Reservation. A couple of additional sights to add to your agenda are Silvio O. Conte National Fish and Wildlife Refuge 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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