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.
Lakeside Inn

Lakeside Inn

2 out of 5
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
7.4/10 Good! (2,199 reviews)
Staff was very friendly and room was clean. Bathroom was very outdated but clean

Reviewed on Aug. 4, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on Aug. 3, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on Aug. 5, 2025

Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
7/10 Good! (157 reviews)
There were a few places to eat near the pier the view of the city was amazing and the tall boat was great for food,dancing and drinking however the vibe is younger college kids. I did enjoy the few places we visited to eat. The parking was horrible, We received no directions and it took us an hour to find someone to check in… I was left with two keys and no directions. I managed and once the sun came up an employee at the front desk named Craig was very helpful. The bed was so uncomfortable I would recommend getting a new more comfortable mattress for the amount we paid. All in all we made the best of it and everything else was okay. Lastly no TV directions I had to purchase Netflix on my own. This was not the best stay provided by Expedia. I was disappointed.

Reviewed on Jul. 31, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
8.8/10 Excellent! (234 reviews)
We enjoyed having the bistro on site.

Reviewed on Jul. 17, 2025

Ready to book your vacation to Chesterfield?

 

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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 refundableReserve now, pay when you stay
The price is CA $127 per night from Aug 24 to Aug 25
CA $127
CA $146 total
Aug 24 - Aug 25
includes taxes & fees
7/10 Good! (1,008 reviews)
"Staff was very friendly. The price was right"

Reviewed on Aug. 4, 2025

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 $132 per night from Sep 7 to Sep 8
CA $132
CA $178 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (543 reviews)
"Very spacious room with full kitchen. Definitely worth the price. Would use again"

Reviewed on Aug. 5, 2025

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 $178 per night from Aug 11 to Aug 12
CA $178
CA $206 total
Aug 11 - Aug 12
includes taxes & fees
9.2/10 Wonderful! (2,241 reviews)
"Clean, comfortable beds and fun live music at the restaurant attached"

Reviewed on Aug. 6, 2025

D. Hotel Suites & Spa
See all 465 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 $512 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.