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Our top choices for Chesterfield hotels

1. The Ellery

The Ellery
3.5 star property
Northampton
9.4 out of 10, Exceptional, (1,001 reviews)
"great and quaint stay"
United States
Adalie
The price is AU$166
includes taxes & fees
9 Dec - 10 Dec
The Ellery

2. Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1,003 reviews)
"We stayed in a spacious, clean bedroom. The staff was friendly and the breakfast had many options"
United States
Claudia
The price is AU$197
includes taxes & fees
11 Dec - 12 Dec
Comfort Inn & Suites Hadley - Amherst

3. River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very good, (308 reviews)
"Super friendly and helpful staff, convenient parking, decently sized room."
United States
Brandon
The price is AU$137
includes taxes & fees
15 Dec - 16 Dec
River Valley Inn

4. 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)
"Great place"
United States
John
The price is AU$147
includes taxes & fees
6 Dec - 7 Dec
Red Roof Inn PLUS+ South Deerfield – Amherst

5. Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst
3.0 star property
Northampton
9.2 out of 10, Wonderful, (1,000 reviews)
"Nice, clean, room; friendly staff; good breakfast options"
United States
Erik
The price is AU$241
includes taxes & fees
7 Dec - 8 Dec
Fairfield Inn & Suites Springfield Northampton/Amherst

6. Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean room, friendly staff"
United States
Gina
The price is AU$215
includes taxes & fees
22 Nov - 23 Nov
Hampton Inn Hadley-Amherst Area

7. TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.6 out of 10, Exceptional, (115 reviews)
"What a lovely property- such a great place to stay when in the Amherst area - staff is excellent- the rooms are all perfect and the amenities are outstanding"
United States
Sarah
The price is AU$236
includes taxes & fees
29 Nov - 30 Nov
TownePlace Suites by Marriott Hadley Amherst

8. Hotel Northampton

Hotel Northampton
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,002 reviews)
"nice place to stay in the heart of downtown Northampton"
United States
Beth
The price is AU$310
includes taxes & fees
27 Nov - 28 Nov
Hotel Northampton

9. Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst
2.5 star property
Northampton
7.2 out of 10, Good, (1,001 reviews)
"The hotel is a great place to stay for a trip in this area."
United States
Ni-Ling
The price is AU$194
includes taxes & fees
13 Dec - 14 Dec
Quality Inn & Suites Northampton - Amherst

10. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,000 reviews)
"Just perfect lodging place for short time travelers"
United States
Bernardo Jr
The price is AU$140
includes taxes & fees
6 Dec - 7 Dec
Quality Inn Lee - Lenox South

11. Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (553 reviews)
"The Old Mill Inn exceeded my expectations! Check-in was easy and seamless, with clear directions to the room. The views were beautiful, the breakfast offerings were amazing, and the innkeeper was incredibly thorough, friendly, and welcoming. I would absolutely stay here again!"
United States
Jaime
The price is AU$312
includes taxes & fees
15 Nov - 16 Nov
Old Mill Inn

12. D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,068 reviews)
"Extremely clean and professional a wonderful stay"
United States
Patrick
The price is AU$203
includes taxes & fees
30 Nov - 1 Dec
D. Hotel Suites & Spa

13. Hotel UMass

Hotel UMass
2.5 star property
Amherst
9.0 out of 10, Wonderful, (1,003 reviews)
"Lovely room, great location, staff excellent"
United States
Lyla
The price is AU$177
includes taxes & fees
15 Dec - 16 Dec
Hotel UMass

14. Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (851 reviews)
"Great breakfast, excellent staff"
United States
Jenny
The price is AU$241
includes taxes & fees
1 Dec - 2 Dec
Homewood Suites by Hilton Hadley Amherst

15. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (985 reviews)
"Staff very pleasant and accommodating."
United States
Rosemarie
The price is AU$188
includes taxes & fees
29 Nov - 30 Nov
Hotel On North

16. Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (790 reviews)
"the room was clean and the staff was so kind"
United States
valerie
The price is AU$235
includes taxes & fees
18 Nov - 19 Nov
Courtyard by Marriott Hadley Amherst

17. Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (151 reviews)
"Like the ambiance as well as the decor! The location was perfect for walking around town!"
United States
Robert
The price is AU$189
includes taxes & fees
15 Nov - 16 Nov
Blooming Inn

18. Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (710 reviews)
"Super clean room, excellent temperature control wihh the the room a/c. Breakfast was hot and fresh, eggs, sausage, fruit, yogurts, oatmeal with all the toppings"
United States
Caroline
The price is AU$206
includes taxes & fees
9 Dec - 10 Dec
Fairfield Inn & Suites Springfield Holyoke

19. Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel
2.0 star property
West Springfield
9.2 out of 10, Wonderful, (410 reviews)
"Great place to stay"
United States
Julian
The price is AU$176
includes taxes & fees
9 Dec - 10 Dec
Blue A Modern Hotel, an Ascend Collection Hotel

20. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,271 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is AU$159
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
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

Recent Reviews in Chesterfield

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

When is the best time to go to Chesterfield?
The best time to go to Chesterfield is during the autumn months, specifically from late September through October.

This period offers stunning natural beauty as the Berkshire Hills transform with vibrant fall foliage. The weather is typically crisp and pleasant, ideal for outdoor activities like hiking, scenic drives, and exploring the local area. You'll find fewer crowds compared to peak summer, allowing for a more relaxed experience.

Couples looking for a romantic getaway will particularly enjoy Chesterfield in the autumn. The picturesque landscapes provide a beautiful backdrop for leisurely drives along Route 143 or walks through the Chesterfield Gorge. Many local inns and bed and breakfasts offer cosy amenities, great for a peaceful escape.

For travellers interested in outdoor pursuits, the autumn weather is great for exploring the many hiking trails in the surrounding state forests, such as the Knightville Dam area. The cooler temperatures make for comfortable walking, and the changing leaves offer spectacular views.
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 cancelled 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 hotel booking in Chesterfield with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Chesterfield hotels. Plus, you'll earn OneKeyCashā„¢* 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. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Chesterfield?
Prices for hotels in Chesterfield often vary, but you can find a great deal from AU$137 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 our cheapest rates.

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