Chesterfield, MA

Travel Guide

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $128 total per night from Dec 3 to Dec 4
$128 total
Dec 3 - Dec 4
Total with taxes and fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
$137 nightly
The price is $153 total per night from Nov 29 to Nov 30
$153 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this spa hotel in Holyoke. Enjoy free breakfast, a full-service spa, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,086 reviews)
"Room : clean Breakfast: variety of good choice Staff: polite and friendly Parking: plenty of available spots"

Reviewed on Nov 4, 2026

D. Hotel Suites & Spa
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
$97 nightly
The price is $108 total per night from Nov 15 to Nov 16
$108 total
Nov 15 - Nov 16
Total with taxes and fees
Stay at this hotel in Amherst. Enjoy free breakfast, free WiFi, and 5 coffee shops/cafes. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hotel UMass
See all 517 properties in Chesterfield
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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
Berkshire Mountain Lodge
Experience Three Sisters Sanctuary in Goshen, MA

Experience Three Sisters Sanctuary in Goshen, MA

Goshen MA
Stay at this vacation home in Goshen. Enjoy a garden and air conditioning. Popular attractions Three Sisters Sanctuary and Swift River are located nearby.
9.6/10 Exceptional! (25 reviews)
"This property was exactly what we needed! The photos were completely accurate but the experience of being in the unit was so much better than the photos could show. The entire apartment was clean and comfortable and the kitchen had everything we needed to cook basic meals. We loved exploring the ..."

Reviewed on Oct 31, 2026

Experience Three Sisters Sanctuary in Goshen, MA
Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass

Otis MA
Stay at this cottage in Otis. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Larkum Pond and Otis Reservoir are located nearby.
8.6/10 Excellent! (10 reviews)
"A fantastic location with a great view of the lake, lots of friendly people, quaint, nice town. Gonna go back."

Reviewed on Jul 23, 2026

Private Island - Largest Fresh Water Reservoir in Mass
See all properties in Chesterfield
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.

Stay near popular Chesterfield attractions

Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest while you're in the area.
See properties

Frequently asked questions

Is Chesterfield worth visiting?
Chesterfield is worth visiting for its natural beauty, highlighted by the Chesterfield Gorge, and its historical landmarks such as the Chesterfield Town Hall. Travelers can also explore a variety of dining experiences, with local restaurants serving delicious Italian and Asian cuisines.
When is the best time to visit Chesterfield?
The best time to visit Chesterfield is from March through May, when the weather is mild and pleasant. For fewer crowds and better value, consider the cooler months of November through January, which may also bring snow. This period offers a different experience with lower visitor numbers and typically more affordable rates.
What is Chesterfield known for?
Chesterfield is known for its natural landmark, Chesterfield Gorge, and its historic Chesterfield Town Hall. Travelers can also explore Krug Sugarbush. The area offers a strong presence of Italian food for travelers to enjoy.
What is a good itinerary length for Chesterfield?
A good itinerary length for Chesterfield is one to two days to explore key highlights like Chesterfield Gorge, Chesterfield Town Hall, and Krug Sugarbush. For an extended stay of three to four days, travelers can enjoy these attractions at a more relaxed pace and sample local dining, including Italian, Asian, and North American cuisine.
What are the top things to do in and around Chesterfield?
Chesterfield offers natural beauty and local landmarks for travelers to explore:

  • Explore Chesterfield Gorge Reservation, a scenic natural area.
  • Visit Chesterfield Town Hall, a significant local landmark.
  • Discover Krug Sugarbush, another beautiful natural point of interest.

How do I plan a trip to Chesterfield?
To plan your trip to Chesterfield, search for places to stay on Expedia. Book flights and activities like visiting Chesterfield Gorge, Chesterfield Town Hall, and Krug Sugarbush in advance. Remember to pair outdoor plans with indoor backups for weather flexibility, ensuring a smooth trip.
What cuisines can you find in Chesterfield?
In Chesterfield you can find Thai cuisine, with dishes like Pad Thai, green curry, and tom yum soup. Travelers can also enjoy Italian favorites such as pasta and pizza, along with Mexican options like tacos and burritos. Various other Asian, North American, and European choices are also available.
Can I book a refundable hotel in Chesterfield?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Chesterfield by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Chesterfield with Expedia?
Expedia makes it easier to plan your Chesterfield trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Chesterfield?
The best choice depends on your travel style. Hotels in Chesterfield can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Chesterfield trip on Expedia?
Once you've booked your Chesterfield trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Chesterfield trip?
Expedia offers customer support before, during, and after your Chesterfield trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Chesterfield?
If it's your first trip to Chesterfield, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Chesterfield hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Chesterfield hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Chesterfield

A rocky stream with cascading water surrounded by trees.

Huntington

Explore a world of travel with Expedia