Chesterfield Vacations from ₩936,050
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 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
The Latest Chesterfield Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
West End
₩1,443,913
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
8.8/10 Excellent! (1,549 reviews)
Very friendly and helpful staff. Clean property top to bottom. Easy walk (3-4 mins) from North Station/TD Gardens and rest of North End is easily walkable. As in any large city, rooms are pretty small, but four adults managed fine. Would certainly stay here again.
Reviewed on Aug 17, 2026
Find the Best Chesterfield Vacation Packages
Chesterfield Hotel Deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
₩172,196
₩201,488 total
Aug 23 - Aug 24
includes taxes & fees
9.2/10 Wonderful! (2,114 reviews)
"Room was clean, quiet and comfortable."
Reviewed on Aug 16, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
₩133,918
₩181,212 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (1,077 reviews)
"The rooms were spotless and a good size. And is not far from Lenox which was our focus. I’d suggest that guests bring some food with them and there is a supermarket nearby. There is not a morsel of food in the ‘resort’. The tv is complicated and I’m not sure why it is set up the way it is. Check ..."
Reviewed on Aug 17, 2026
Hotel Northampton
36 King Street Northampton MA
₩210,228
₩234,818 total
Aug 18 - Aug 19
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"Excellent reception desk and very professional. The hotel is gorgeous and very clean. The hotel also has excellent accessibility and parking."
Reviewed on Aug 15, 2026
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.
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 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.
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.
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.
Frequently asked questions
How much does a Chesterfield vacation package cost?
You'll find cheap prices from ₩936,050 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?
You can usually find reduced prices and greater availability in January, February and November. Browse our cheap Chesterfield vacation packages and you could get some excellent off-season deals.
How many days is enough for Chesterfield?
With a well-organized travel plan, you can easily visit the top Chesterfield sights in a handful of days. But if you'd like to venture off the beaten track or take day trips, 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.
How to plan a trip to Chesterfield?
- Pick your dates: The things you'd like to do in Chesterfield and your preferred season will help you decide when to get away.
- Budget wisely: Besides the cost of your stay, you'll need to factor in other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Chesterfield.
- Set the duration of your trip: Start by compiling a list of the activities and sights you want to experience in Chesterfield. Then, estimate how long you'll need at each, as well as any travel time.
- Combine your accommodations and airfare: After you've settled on your travel dates and duration, book the right Chesterfield vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
