Chesterfield Holidays

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Top Flight + Hotel Deals in Chesterfield

Price found within the past 48 hours. Click for updated prices.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
per person
18 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (2,098 reviews)
Tiny hotel rooms! Convenient for a quick business trip 1 or 2 days. Anything longer, send extra for more space.

Reviewed on 31 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
18 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
The bed and room were very comfortable with a lovely view. The gym was fabulous. The restaurant has a very limited menu with few to none green simple salad option or vegetables-all the meals we chose were well prepared with good service but pricey.

Reviewed on 1 Aug 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
1 Sept - 8 Sept
found 2 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (1,009 reviews)
Beautiful hotel located right in the heart of the city! Nice big room with a big bathroom. Located near all the shopping and great restaurants. Also very close to the T station and very safe!

Reviewed on 28 Jul 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
1 Sept - 8 Sept
found 2 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (227 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

2 out of 5
South End
per person
1 Sept - 8 Sept
found 2 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
7.4/10 Good! (114 reviews)
Property is located in a very nice area. No frill, what they advertise, you get.

Reviewed on 23 May 2025

Top hotels in Chesterfield

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 €112 per night from 3 Aug to 4 Aug
€112
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (2,262 reviews)
Perfect getaway!
"The bed was so comfortable! The room had everything one could want: plugs for charging, mirrors, temperature control, warm shower. Breakfast was good and the coupon for Delaney House was much appreciated"

Reviewed on 29 Jul 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 €163 per night from 6 Aug to 7 Aug
€163
6 Aug - 7 Aug
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Good and convenient for orientation at umass."

Reviewed on 20 Jul 2025

Hotel UMass
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is €70 per night from 17 Aug to 18 Aug
€70
17 Aug - 18 Aug
includes taxes & fees
5.2/10 (758 reviews)
"Will stay at again."

Reviewed on 1 Aug 2025

FairBridge Inn Express
See all 463 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.

Popular places to visit

Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forests while you're in the area.

Chesterfield Gorge

Frequently asked questions

How much does a Chesterfield holiday package cost?
You'll find cheap prices from €818 on Expedia for your Chesterfield getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your holiday 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 holiday packages and you could get some excellent off-season deals.
How many days is enough for Chesterfield?
With a well-organised 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 holiday 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 holiday as a package?
You can enjoy significant savings on your next Chesterfield retreat by booking a personalised holiday 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 holiday package to Chesterfield?
If you have your Chesterfield holiday 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?

  1. Pick your dates: The things you'd like to do in Chesterfield and your preferred season will help you decide when to get away.
  2. 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.
  3. 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.
  4. Combine your accommodation and airfare: After you've settled on your travel dates and duration, book the right Chesterfield holiday package for you.

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