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.
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $1,254, price is now CA $761 per person
CA $761
per person
Aug 20 - Aug 23
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (177 reviews)
Great hotel staff, great location, great room :)

Reviewed on Jul 8, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $1,956, price is now CA $1,320 per person
CA $1,320
per person
Aug 21 - Aug 25
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (258 reviews)
Staff was super friendly and accommodating, and we very much enjoyed our stay. Room was good, location is great right on the edge of town and easily accessible.

Reviewed on Jul 8, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,502, price is now CA $2,440 per person
CA $2,440
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $2,772, price is now CA $1,957 per person
CA $1,957
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,301, price is now CA $933 per person
CA $933
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The location couldn’t have been more perfect and despite it being a holiday weekend the parking lot/BNB never felt crowded. Everyone we encountered was lovely and helpful, and the room was a perfect place to take a midday nap or unwind after hours on the beach! We would definitely stay again.

Reviewed on Jul 6, 2026

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Chesterfield Hotel Deals

Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Fully refundable
The price is CA $138 per night from Jul 23 to Jul 24
CA $138
CA $158 total
Jul 23 - Jul 24
includes taxes & fees
7/10 Good! (1,012 reviews)
"The front desk during the day on Monday and Tuesday during my day was horrible very rude. Definitely should not be greeting your guest at the door."

Reviewed on Jul 8, 2026

Quality Inn West Springfield
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Aug 9 to Aug 10
CA $190
CA $244 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (1,025 reviews)
"Nice property good coffee"

Reviewed on Jul 6, 2026

Berkshire Mountain Lodge
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 $183 per night from Jul 20 to Jul 21
CA $183
CA $214 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (2,129 reviews)
"Excelente hotel bonito limpio el personal muy atento y agradable la habitación grande buen aire acondicionado un desayuno variado y exquisito y acabado de preparar"

Reviewed on Jul 7, 2026

D. Hotel Suites & Spa
See all 508 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
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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

How much does a Chesterfield vacation package cost?
You can snap up a vacation package to this top destination from CA $761 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.

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