Chesterfield Vacation Packages

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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.

Top Chesterfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
The air conditioner sound like a truck trailer was in your room

Reviewed on Jul. 11, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 12 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 12 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Appreciated the free airport shuttle on demand

Reviewed on Jul. 9, 2025

Ready to book your vacation to Chesterfield?

 

Choose your dates

Chesterfield Hotel Deals

D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Jul 27 to Jul 28
CA $150
CA $175 total
Jul 27 - Jul 28
includes taxes & fees
9.2/10 Wonderful! (2,266 reviews)
We will be back very soon!
"What a warm welcome. Front desk was most welcoming. Very nice swim & hot tub! Great breakfast!"

Reviewed on Jul. 9, 2025

D. Hotel Suites & Spa
Hotel UMass
Hotel UMass
2.5 out of 5
1 Campus Center Way, Amherst, MA
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Jul 23 to Jul 24
CA $215
CA $243 total
Jul 23 - Jul 24
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Nice and clean hotel in the center of UMass."

Reviewed on Jul. 11, 2025

Hotel UMass
Quality Inn West Springfield
Quality Inn West Springfield
2.5 out of 5
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Aug 1 to Aug 2
CA $124
CA $142 total
Aug 1 - Aug 2
includes taxes & fees
7/10 Good! (1,006 reviews)
"Safe and convenient"

Reviewed on Jul. 11, 2025

Quality Inn West Springfield
See all 457 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
You can snap up a vacation package to this top destination from CA $705 on Expedia. However, how much your vacation to Chesterfield costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Chesterfield?
January, February and November are great times to look for cheap Chesterfield vacation packages. Opting to travel in less busy periods means you can usually find reduced prices on flights and hotels.
How many days is enough for Chesterfield?
You can easily explore all the top attractions in Chesterfield within a few days, including the must-see Chesterfield Gorge. If you're after a longer Chesterfield vacation, look at which kind of day trips and activities are available close by.
How to find the best Chesterfield package deals?
Use Expedia's filter tool to find some great Chesterfield package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Chesterfield package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your Chesterfield getaway by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to see the best hotel prices and airfares. 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 travel dates locked in, book early to score some outstanding deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Chesterfield?

  1. Choose your travel dates: What you'd like to do in Chesterfield and your favourite season will help you decide when to travel.
  2. Plan your budget wisely: As well as the cost of your stay, you should consider other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that could crop up during your trip to Chesterfield.
  3. Decide how long to go away for: Now that you're more familiar with Chesterfield, you can work out the perfect length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Chesterfield vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.