Search for Cheap Deals onHotels in Chesterfield
Choose from 502 Chesterfield Hotel Deals
D. Hotel Suites & Spa
Excellent
Reviewed on Jan 20, 2026
Berkshire Mountain Lodge
Clean, great location near Bosquet Mountain and grocery store, spacious condo, easy.
Reviewed on Jan 19, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
generally good
Reviewed on Jan 19, 2026
Courtyard by Marriott West Springfield
Clean, great area, and welcoming.
Reviewed on Jan 8, 2026
Comfort Inn & Suites
Room looked newly renovated. The entire building was spotless including the breakfast area. Comfortable bed and sofa. Could have used some real dishes and glasses.
Reviewed on Jan 20, 2026
Tru by Hilton Chicopee Springfield
Johnathan at the front desk is a prime example of exemplary customer service. I was blown away by his willingness to help all guests not just myself.
Reviewed on Jan 19, 2026
Red Roof Inn PLUS+ South Deerfield – Amherst
Execellent
Reviewed on Jan 16, 2026
The Ellery
Each visit, I've found the rooms, bed and bath clean and comfortable. The breakfast options are very thoughtful and help me start the day well. The staff at check in and check out are kind and attentive. It is nice to enjoy time by a fireplace, and the occasional puzzle at a table is a fun ...
Reviewed on Jan 19, 2026
Hotel Northampton
Room was clean but small. Hotel lobby was beautiful so room was a little disappointing
Reviewed on Jan 22, 2026
Blue – A Modern Hotel, an Ascend Collection Hotel
Clean and comfortable rooms including a massage chair. Fresh baked cookies daily. Very friendly staff...every single one of them. Fresh muffins baked for continental breakfast, but I missed them because I woke up late every day...lol
Reviewed on Jan 23, 2026
Riverdale Inn
There is working being done to the space infornt on the Hotel. That was poor driving in, potholes were trouble. The place we stayed was clean and kind and not bad to stay.
Reviewed on Jan 15, 2026
Hotel On North
It can be hard trying to choose a place to stay lately, especially since AI has blown up. I'm so happy I gave this place a chance. The staff was extremely friendly and helpful. Not once did I feel like they didn't want to be there. When we checked out at noon (which is an amazing checkout time), ...
Reviewed on Jan 18, 2026
Find cheap hotels in Chesterfield
You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Chesterfield hotel with Hotwire to complete your one-of-a-kind travel checklist.
For you, intrepid voyager, Hotwire has a large selection of the best hotels in Chesterfield.
Choosing the right hotel in Massachusetts has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Chesterfield’s 502 hotels. Choose the one that best catches your trip’s tourist drift.
If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $93. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Chesterfield hotel deals at the last minute.
While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Chesterfield. No matter your reason for visiting Chesterfield, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.
Frequently Asked Questions About Chesterfield hotels
Where can I find the best last-minute travel deals?
If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Chesterfield for as low as $93.
How many hotels are there in Chesterfield?
With over 502 hotels in Chesterfield, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $93.
How to find cheap car rentals in Chesterfield?
Finding a cheap car rental deal in Chesterfield is as easy as scoring cheap hotels in Chesterfield. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.
- Hotels near Chesterfield Gorge
- Hotels near University of Massachusetts Amherst
- Hotels near Amherst College
- Hotels near Berkshire East Ski Resort
- Hotels near Big E
- Hotels near Mount Holyoke College
- Hotels near Smith College
- Hotels near Holyoke Mall
- Hotels near Connecticut River
- Hotels near Hampshire College
- Hotels near Jacob's Pillow
- Hotels near Lee Premium Outlets
- Hotels near Historic Northampton
- Hotels near Deerfield Academy
- Hotels near Academy of Music Theater
- Hotels near Olympia Ice Center
- Hotels near Historic Deerfield Village
- Hotels near Emily Dickinson Museum
- Hotels near Eric Carle Museum of Picture Book Art
- Springfield Hotels
- Lenox Hotels
- The Berkshires Hotels
- Pittsfield Hotels
- Northampton Hotels
- Amherst Hotels
- West Springfield Hotels
- Lee Hotels
- Holyoke Hotels
- Chicopee Hotels
- North Adams Hotels
- Appalachian Mountains Hotels
- Greenfield Hotels
- Hadley Hotels
- Westfield Hotels
- Charlemont Hotels
- Western Massachusetts Hotels
- Otis Hotels
- Easthampton Hotels
- Shelburne Falls Hotels
