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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, (130 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is AU$213
includes taxes & fees
8 Feb - 9 Feb
Blooming Inn

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (911 reviews)
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
United States
Gloria
The price is AU$139
includes taxes & fees
27 Feb - 28 Feb
Quality Inn Westfield - Springfield

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (825 reviews)
"I will stay again"
United States
Jailene
The price is AU$195
includes taxes & fees
26 Feb - 27 Feb
Hampton Inn Westfield

Inn on Boltwood

Inn on Boltwood
3.0 star property
Amherst
9.4 out of 10, Exceptional, (762 reviews)
"It is a beautiful and historic property with an amazing restaurant and bar."
United States
Kelly
The price is AU$328
includes taxes & fees
10 Feb - 11 Feb
Inn on Boltwood

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, (81 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is AU$211
includes taxes & fees
26 Feb - 27 Feb
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1,003 reviews)
"Friendly staff, access to a meal during a snowstorm, under-roof parking also during a snowstorm and a very clean room."
United States
Kevin
The price is AU$201
includes taxes & fees
9 Feb - 10 Feb
Hotel UMass

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (665 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is AU$219
includes taxes & fees
27 Feb - 28 Feb
Hilton Garden Inn Lenox Pittsfield

Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (690 reviews)
"My son and I stayed during a big snow storm, staff not only got us checked in early but were super friendly and helpful. Hotel was also relatively spotless and clean given the circumstances with the storm."
United States
William
The price is AU$228
includes taxes & fees
10 Feb - 11 Feb
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, (728 reviews)
"The room was efficient, clean and spacious. The pool was great and so was the breakfast. "
United States
Julianne
The price is AU$223
includes taxes & fees
12 Feb - 13 Feb
Homewood Suites by Hilton Hadley Amherst

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (821 reviews)
"Great staff, beautiful hotel. Would definitely recommend "
United States
Shawn
The price is AU$237
includes taxes & fees
8 Mar - 9 Mar
Hotel On North

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 AU$158
includes taxes & fees
24 Feb - 25 Feb
Elm Motel

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (975 reviews)
"Best hotel in the area, hands down"
United States
alexander
The price is AU$197
includes taxes & fees
18 Feb - 19 Feb
Hampton Inn Hadley-Amherst Area

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (355 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is AU$161
includes taxes & fees
1 Mar - 2 Mar
The Central Downtown Inn & Suites

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (826 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is AU$190
includes taxes & fees
8 Feb - 9 Feb
Berkshire Mountain Lodge

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
9.8 out of 10, Exceptional, (101 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

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 AU$276
includes taxes & fees
6 Feb - 7 Feb
The Trail in Adams - Berkshires’ Art Hotel

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.8 out of 10, Exceptional, (62 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 AU$237
includes taxes & fees
12 Feb - 13 Feb
TownePlace Suites by Marriott Hadley Amherst

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (842 reviews)
"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 AU$135
includes taxes & fees
15 Feb - 16 Feb
Berkshire Inn

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 AU$324
includes taxes & fees
9 Feb - 10 Feb
Harbour House 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, (1,001 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is AU$162
includes taxes & fees
7 Mar - 8 Mar
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 accommodation in Chesterfield

Find out more about Chesterfield

Top reasons to visit Chesterfield

  • Outdoor Adventures: Chesterfield is a haven for outdoor enthusiasts, offering activities like skiing, hiking, and camping amidst stunning landscapes.
  • Cultural Experiences: Explore local heritage at the Chesterfield Museum and the scenic Chesterfield Canal for a taste of the town's history.
  • Charming Town Centre: The welcoming atmosphere of the town centre, filled with friendly locals, enhances your visit.
  • Diverse Accommodation: From family-friendly to pet-friendly options, Chesterfield caters to all types of travellers.
  • Scenic State Parks: Nearby state parks provide additional opportunities for relaxation and adventure in nature.

Find great hotels near Chesterfield

Discover the charm of Chesterfield, Massachusetts, with a range of accommodation options that cater to all types of travellers. From family-friendly stays to pet-friendly hotels, Chesterfield offers a unique blend of agritourism and stylish lodgings. Whether you’re seeking a business-focused hotel or a relaxing getaway, you’ll find the perfect base to explore this picturesque area.

  • D. Hotel Suites & Spa: Nestled 22.5km from Chesterfield, D. Hotel Suites & Spa is a delightful retreat for those seeking a romantic or family getaway. This 3-star property is perfect for couples wishing to indulge in a spa-themed experience, featuring amenities like Deep Tissue and Hot Stone massages, a sauna, and a full-service spa. Guests can savour romantic dining options with room service and nearby winery tours, along with exclusive romance packages. For families, the hotel provides child-friendly amenities, ensuring a relaxing stay for travellers of all ages.
  • Red Roof Inn PLUS+ South Deerfield – Amherst: Located 20.9km from Chesterfield, Red Roof Inn PLUS+ South Deerfield – Amherst is an inclusive and pet-friendly accommodation. Emphasising a warm welcome for LGBTQIA travellers, this property allows pets with specific restrictions and offers amenities that cater to furry companions. Guests can rest easy knowing their service animals are welcomed without fees. This hotel is ideal for those looking for a comfortable stay with the option to bring their pets along, ensuring everyone in the family feels at home.
  • Howard Johnson by Wyndham Amherst Hadley: Situated 24.1km from Chesterfield, Howard Johnson by Wyndham Amherst Hadley is a family and pet-friendly haven. With complimentary cribs for little ones and a welcoming atmosphere for pets, this hotel is designed for comfort and convenience. Families can enjoy spacious rooms while pets can accompany them without hassle. The hotel also waives fees for service animals, making it a perfect choice for those travelling with furry friends. With a focus on family-oriented amenities, this property ensures an enjoyable stay for all.

Where to stay near Chesterfield

Chesterfield, Massachusetts, offers a delightful blend of outdoor adventures and scenic beauty, perfect for a family getaway or a romantic escape. Explore the charming town centre, where friendly locals create a welcoming atmosphere. Nearby attractions provide opportunities for relaxation and adventure, ensuring a memorable experience. Whether you're hiking the stunning landscapes or enjoying the quaint ambiance of the Welcome to Chesterfield House, this region promises an unforgettable holiday filled with diverse vibes.

  • Northampton: Situated 17.7km from Chesterfield, Northampton is a vibrant city steeped in culture and history. Known for its lively arts scene, visitors flock here for a blend of cultural experiences, outdoor activities, and urban exploration. The city is home to historic and modern colleges, making it a hub for educational events and concerts. Nature enthusiasts can enjoy nearby lakes and parks, while foodies will love the diverse dining options. Peak travel months are April, July, and September, providing a great atmosphere for exploring the city's rich offerings.
  • Western Massachusetts: Just 3.2km from Chesterfield, Western Massachusetts is a stunning region that captivates outdoor lovers and adventure seekers alike. With a focus on scenery and exploration, this area boasts ski fields and resorts that draw visitors year-round, especially in the summer and autumn months. Outdoor activities abound, from hiking in national state parks to enjoying tranquil moments by the lake. The stunning mountains provide a picturesque backdrop for all your adventures, making it a must-visit for those seeking natural beauty.
  • Goshen: Located 6.4km from Chesterfield, Goshen is a charming city known for its picturesque landscapes and romantic ambiance. Visitors are drawn to this area primarily during the summer months when outdoor activities flourish. Enjoy the local resorts and recreational areas, or explore the nearby national state parks for a taste of nature's splendour. The local art gallery adds a cultural touch, making it a perfect spot for those looking to unwind and appreciate the beauty and creativity of the surroundings.

Things to do near Chesterfield

Chesterfield, Massachusetts offers a fantastic getaway for outdoor enthusiasts, featuring activities like skiing and exploring scenic landscapes. Visitors can enjoy a day filled with adventure, including camping at picturesque sites. Whether you're keen to hit the slopes or simply soak in the natural beauty, Chesterfield provides a perfect backdrop for a memorable holiday.

Shopping

For a delightful shopping experience in Chesterfield, visit the Don Muller Gallery, located 19.3km away. If you're up for a drive, check out Holyoke Mall and Holyoke Crossing, both offering a mix of family-friendly shops and vibrant city vibes, about 19 and 29.0km away, respectively.

Recreation

Experience the magic of Jacob's Pillow, a renowned dance venue 27.4km from Chesterfield, offering vibrant performances and cultural immersion. For relaxation, head to Land of Providence, 16.1km away, where you can unwind amidst nature. Mullins Center, 25.7km away, is perfect for sports enthusiasts seeking excitement.

Adventure

Experience the Look Memorial Park Tennis Center, located 14.5km from Chesterfield, where you can enjoy tennis surrounded by adventure vibes. For hiking enthusiasts, the Skyline Trail, 16.1km away, offers stunning scenery and outdoor excitement. If you're into skiing, the Blandford Ski Area, 22.5km away, promises thrilling slopes.

Nightlife

In Chesterfield, the Academy of Music Theater offers a charming atmosphere with cultural performances, just 19.3km away. Spare Time Bowling, also 19.3km out, provides a fun-filled adventure for families, while Cinemark At Hampshire Mall, 24.1km away, showcases the latest films in a romantic setting.

Booking tips and Expedia advantages for Chesterfield

When visiting Chesterfield, Massachusetts, save money by travelling during the cheaper months of March or December to January, and avoid peak times like July and August. Stay on a Tuesday for the lowest rates. Use Expedia’s search tool to find budget-friendly hotels, filter by Eco-certified options, and consider package deals that combine flights and accommodations for extra savings. Additionally, explore free local activities to enhance your experience without breaking the bank.

  • 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: Expedia’s search tool makes it easy to tailor your travel experience to your budget and preferred location, among other options. You can organise your search results to display prices from the lowest to the highest, ensuring you find the most affordable hotels right away. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that you can book.
  • Consider bundling your trip: You can save some cash by combining your Chesterfield hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Chesterfield

Chesterfield, Massachusetts, offers a delightful blend of outdoor adventures and cultural experiences perfect for families and travellers alike. Explore the historic and modern colleges and universities, along with the stunning landscapes of nearby state parks. Don't miss the Chesterfield Museum and the scenic Chesterfield Canal for an enriching experience. This charming town is sure to leave a lasting impression on your holiday.

  • University of Massachusetts Amherst: This modern university offers a vibrant city atmosphere with its bustling campus life, diverse student body, and a variety of cultural events. Explore art galleries, attend performances, and enjoy the beautiful grounds filled with scenic walking paths.
  • Smith College: Rich in history and culture, Smith College is renowned for its stunning architecture and lush gardens. Visitors can stroll through the botanic garden, visit the museums, and appreciate the college's commitment to women's education in a serene and inspiring environment.
  • Berkshire East Ski Resort: Perfect for adventure enthusiasts, this ski resort features diverse slopes for all skill levels, along with thrilling outdoor activities year-round. Experience the breathtaking views while skiing, snowboarding, or mountain biking in a picturesque setting.

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 trip to Chesterfield, Massachusetts, you can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is approximately 53.1km away, with nearby hotels like the 4-star Simsbury 1820 House, 11.3km from the airport, and the 3.5-star Sheraton Hartford Hotel located right at the airport. Albany, NY (ALB-Albany Intl.) is about 88.5km away, offering options such as the 4-star Landing Hotel at Rivers Casino & Resort, 12.9km from the airport. Lastly, Worcester, MA (ORH-Worcester Regional) is around 80.5km away, with great accommodation choices like the 4-star Beechwood Hotel just 8.0km away 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 traveller data. Two other choices for your visit to the area are Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or vacation rentals in Chesterfield.
What are some of the best holiday rentals that Chesterfield has to offer?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Chesterfield offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. See all vacation rentals in Chesterfield.
If I need to cancel my hotel reservation in Chesterfield, will I receive a refund?
Yes, you'll find most hotel room reservations are refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, it might still be possible to cancel it and be given a refund within a 24-hour period 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 506 hotels and other accommodation options in the surrounding area. Find out more about Chesterfield.
What should I do while I'm visiting Chesterfield?
Natural beauty is on display at Chesterfield Gorge, Knightville Dam & Reservation and Westfield River. A couple of additional sights to add to your itinerary are Chesterfield Public Library and Chesterfield Town Hall. Take a look at what more there is to see and do in Expedia's Chesterfield guide.
What's the seasonal weather in Chesterfield?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Chesterfield are January, February, November and March, with each month seeing an average of 16 cm of snowfall.

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