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.
Sea Mist Resort

Sea Mist Resort

3 out of 5
per person
Jun. 5 - Jun. 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.8/10 Excellent! (115 reviews)
Did not like that I could hear the person walking in the rooms above me

Reviewed on Apr. 29, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Jul. 6 - Jul. 12
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (234 reviews)
Beautiful accommodations and unique character

Reviewed on Nov. 6, 2024

The Cove At Salem

The Cove At Salem

3 out of 5
Save 100% on your flight
per person
Jul. 10 - Jul. 14
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (459 reviews)
This was a cute cozy little suite! It was perfect for a small girls trip getaway! The only thing missing was a microwave in the room. It was nice to have access extra towels and blankets available without calling to have them brought. Staff was kind and friendly!

Reviewed on Apr. 24, 2025

The Beverly

The Beverly

3 out of 5
per person
Jul. 10 - Jul. 14
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (277 reviews)
Communication was fantastic.

Reviewed on Feb. 27, 2025

XV Beacon

XV Beacon

5 out of 5
Beacon Hill
Save 100% on your flight
per person
Jul. 10 - Jul. 14
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
9.4/10 Exceptional! (370 reviews)
Beautiful large well appointed room and friendly attentive staff. The curtesy car is a nice extra as well as the attached restaurant/bar.

Reviewed on Feb. 23, 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
The price is CA $155 per night from May 4 to May 5
CA $155
CA $180 total
includes taxes & fees
May 4 - May 5
9.2/10 Wonderful! (2,296 reviews)
"Really nice hotel. Quiet location, clean, good breakfast options. The front desk staff member who checked my in was awesome. He went above and beyond for us."

Reviewed on Apr. 27, 2025

D. Hotel Suites & Spa
Howard Johnson by Wyndham Amherst Hadley
Howard Johnson by Wyndham Amherst Hadley
2 out of 5
401 Russell St, Hadley, MA
The price is CA $152 per night from May 4 to May 5
CA $152
CA $169 total
includes taxes & fees
May 4 - May 5
7.2/10 Good! (1,001 reviews)
"Very friendly staff; breakfast was decent; Very confusing to find rooms 1001-3; room was very low on toilet paper and tissues when we got there; the sidewalks in the front had over grown trees covering them; the hotel overall felt clean and safe."

Reviewed on Apr. 21, 2025

Howard Johnson by Wyndham Amherst Hadley
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
400 Russell St, Hadley, MA
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from May 5 to May 6
CA $175
CA $196 total
includes taxes & fees
May 5 - May 6
9.2/10 Wonderful! (1,008 reviews)
"loved it , would recommend and come again only downfall was our card randomly stopped working but they were communicative with us and got it back working quickly"

Reviewed on Apr. 28, 2025

Comfort Inn & Suites
See all 462 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 $929 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.