Chesterfield Vacations from $584
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Chesterfield Vacation
Skip the stress of organizing your next big adventure with a Chesterfield vacation package. Whether you're in town for its art, food, architecture or something else, this city offers countless exciting experiences to delve into. A trip to Chesterfield is an excellent opportunity to take in the sights. Check out renowned attractions like Chesterfield Gorge, Swift River and Petticoat Hill. Your perfect Chesterfield vacation is just clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored to suit your style.
The Latest Chesterfield vacation packages
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
$1,173
per person
Dec 18 - Dec 22
found 2 days ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
This hotel is one of, if not the, nicest hotels I have ever stayed at around the world. The level of service is second to none, and hotel itself, physically, is incredibly elegant. Being situated on Boston Harbor puts this hotel over the top and into a class of its own.
Reviewed on Oct 16, 2026
Raffles Boston
Back Bay
$1,129
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.6/10 Exceptional! (332 reviews)
A stunning hotel with super helpful staff. Would highly recommend the Raffles, from start to finish it was excellent and we’ll definitely be back.
Reviewed on Oct 14, 2026
Don't see what you're looking for?
See all available trips from Columbus to Chesterfield
View all tripsStay 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.
Chesterfield Gorge Reservation
You can take time to visit Chesterfield Gorge Reservation during your travels to Chesterfield. Amble around the area's parks or visit its shops.
Chesterfield Town Hall
After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Amble around the area's parks or visit its shops.
Chesterfield Public Library
Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.
Oak Hill
Commune with nature and explore the great outdoors at Oak Hill during your travels in Chesterfield. Amble around the area's parks or visit its shops.
Krug Sugarbush
You can take time to visit Krug Sugarbush during your travels to Chesterfield. Amble around the area's parks or visit its shops.
Chesterfield Hotel Deals
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Fully refundable
$88 nightly
$101 total
Nov 15 - Nov 16
Total with taxes and fees
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundable
$125 nightly
$139 total
Oct 29 - Oct 30
Total with taxes and fees
9.2/10 Wonderful! (2,081 reviews)
"Excellent, helpful staff. Nice breakfast. Convenient location just a short drive to Northampton. Loved the in-room electric fireplace."
Reviewed on Oct 16, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$113 nightly
$126 total
Nov 16 - Nov 17
Total with taxes and fees
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.
Find the Best Chesterfield Vacation Packages
Chesterfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,200 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Historic Northampton, Academy of Music Theater and Calvin Theatre and Performing Arts Center |
More vacations you might like
Frequently asked questions
How much does a Chesterfield vacation package cost?
You'll find cheap prices from $584 on Expedia for your Chesterfield getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
November, December and January are the best times to search for cheap Chesterfield vacation packages. Opting to travel in less busy months means you can typically find better prices on accommodations and flights.
How many days is enough for Chesterfield?
With a well-organized travel plan, you can easily tick off the most popular Chesterfield attractions in a handful of days. But if you'd like to explore off the beaten track or go on day tours, think about booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Landing a cheap Chesterfield package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Chesterfield package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your next Chesterfield retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chesterfield?
If you have your Chesterfield vacation dates finalized, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Your Chesterfield break should be a relaxing escape from your busy life, not a source of money-related stress. So to give you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
Explore a world of travel with Expedia
- Marriott Hotels & Resorts Hotels in Northampton
- Romantic in Western Massachusetts
- Bedandbreakfast in Western Massachusetts
- Cabins in Western Massachusetts
- Hotels in Cummington
- Hotels in Northampton
- Hotels in Haydenville
- Spa in Western Massachusetts
- Hilton Hotels in Northampton
- 5 Star Hotels in Northampton
- Hotels in Williamsburg
- 4 Star Hotels in Western Massachusetts
- Hotels in Florence
- Flights to Western Massachusetts
- Flights to Plainfield
- Flights to Southampton
- Flights to Amherst
- Oceanic Airlines Flushing (LGA) to Westfield (BAF) flights
- Flights from Jamaica (JFK) to Westfield (BAF)
- JetBlue Airways Orlando (MCO) to Worcester (ORH) flights
- Delta Air Lines Detroit (DTW) to Worcester (ORH) flights
- Flights from Arlington (DCA) to Westfield (BAF)
- Flights to Shelburne Falls
- Flights to Northampton
- Western Massachusetts All Inclusive Vacation Packages
- Visit Northampton
- Visit Amherst
- Visit Holyoke
- Adams Vacations
- Tanglewood Music Center
- Naumkeag Museum
- Where to stay in Shelburne Falls
- Western Massachusetts All Inclusive Vacation Packages
- Naismith Memorial Basketball
- Where to stay in Great Barrington
- East Village Historic District Vacations
- Visit Shelburne Falls
- Where to stay in Ashuwillticook Rail Trail
- Northampton Vacations
- Where to stay in The Berkshires
- Western Massachusetts All Inclusive Vacation Packages
- Where to stay in Greenfield
- Where to stay in Western Massachusetts
- Where to stay in Northampton
- Drury Vacations
- Visit Otis
- Visit Western Massachusetts
- Otis Vacations
- Western Massachusetts All Inclusive Vacation Packages
- Southampton Vacations
- Visit Becket
- Six Flags New England
- Western Massachusetts All Inclusive Vacation Packages
- Visit Turners Falls
- Visit Easthampton
- Springfield Vacations
- Western Massachusetts All Inclusive Vacation Packages
- Western Massachusetts All Inclusive Vacation Packages
- Visit Southampton
- Where to stay in Stockbridge
- Orange Vacations
- Where to stay in Mohawk Trail State Forest
- Western Massachusetts All Inclusive Vacation Packages
- Visit Hatfield
- Where to stay in Hadley
- Western Massachusetts All Inclusive Vacation Packages
- Western Massachusetts All Inclusive Vacation Packages
- Western Massachusetts All Inclusive Vacation Packages
- New Salem Vacations
- Where to stay in Amherst
- Western Massachusetts All Inclusive Vacation Packages
- Visit Hadley
- Where to stay in Holyoke
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
